ffi

I6I
 General Organic Chemistry

lsomerism (Structurat & Stereoisomerism)

Grignard Reagent

Hydrocarbons (Alkanes)

Hyd rocarbons (Atkenes)

Hyd rocarbons (Atkynes)

Atkyt Hatides (Substitut'ion Reaction)

Atkyt Halides (Etimination Reaction)

Atkyt Hatides

Atcohot, Ether and Epoxides

Atdehydes and Ketones

Atdot and Cannizaro Reaction

Carboxytic Acid and their Derivatives

Amines

Carbene and Nitrene

Aromatic Compounds

Practical Organic Chemistry

Biomotecutes

{5 , IUPAC Names

Learning Chart
'
 ffiffiHffiT HUfiNIC. G.HiEffiil THr

1. How many 20 Hydrogen atoms are present in the given follon-ing compound ?

(a) 2 (b) s ,(c) 7 (d) 8

Identify which functional group are Not present in the given follor,r,ing compound ?

A/ruu
(a) Ketone (b) Ester
A,) (c) tunide (d) Ether
3. Correct energy profile for amine inversion and hybridization of nitrogen in transition state is:
,zNr
Hli-"sH.
D
l;r
D \N/
(A) (B)
 sp3

(b) 4,,,
,^/

4.
>< (0

Compare the heats of combustion of above compounds:

(a) (i)>(ii)>(iii) (b)(i)>(iii)>(ii) (c) (ii)>(i)>(iii) (d)(ii)>(iii)>(i)
Which of the following is not a resonance structure of the others ?

(a) (b) (c) (d)

6. Rank the hydrogen atoms (H", Hu, H.) in the following molecule according to their acidic

I
strength.

o
Hzc
cHs

(a)a>b>c (b)b>a>c (c) b>c>a (d)c>b>a

o
il
7. cHs
- a;oTcHr;
Compare the bond lengths c and b.
(a) a-b (b)b>a
(c) b<a (d) Impossible to predict
 8. The number of spz -sp2 sigma'bonds in the compound given below is :

(a) 1 (b) s (c) + (d) s

9. The total number of lone pair of electrons in the given molecule is :

,-.
O N-H
(a) 2 (b) s (c) 4 (d) s

ff
10. Which of the following rings is highly strained ?

(a)
,<:
\--ro .i"
LJ-
8-lactone
o)y-lactone (c) l_o
p-lactone
Cal
-J(
o

L--,* -'
6-lactam
11. The functional groups present in Cortisone are :

HOH

(a) Ether, alkene, alcohol O) Alcohol, ketone, alkene, ether

(c) Alcohol, ketone, amine (d) Ether, amine, ketone
12. Select the acid with the higbestKu (i.e.,lowest pK").

o o
Ao, oH AAou
(a) Hsc ,0,:lT\' (c)
r
(d) cl,\)
13. Most stable carbocation among the given example is :

@I
(b). ./\../
I

(d) * cH,
14. Set the following in increasing order of their pKo values.
oo
(x) cH,
-H-o-H lt
0) cHg -U-o-H (z) cH3
-oH
o
(a)y<x<z (b)x<y<z (c)y<z<x (d)x<z<y
 I

L5, Which is the major product of the following reaction ?

t'
H

eeJ. -#
Product

HH
\(r7

,,,en. H
(b)Gfd..
f,T
,.,ef_J.. ,.,er:T.'
HH
L6. In the given pair identify most acidic compound in (A) and (B). Most basic in (C) and (D).

cHs cHs
(A)
(D

NHz

(c)o (D)

(D

(a) A-I, B-II,C-I,D-II o) A-II, B-I,C-I,D-II

(c) A- II, B - II, C -II, D - II (d) A-I, B-lI,C-I,D-I
1-7, Several factors (steric, electronic, orbital interactions etc.) can affect the inversion barrier of
an amine. In the given pair which data is correctly placed ?
Me i-Pr
I I

Ys - P'IN\M.
(a) M.'N-M. i

AG*- T.gkcaVmol AG* : O.2kcal,/mol

(b) -*-*.'
A*n 1-N-,,a.
AG*- 2o"SkcaVmol AG* :7.okcallmol
 Me C1
I I
Ys

(c) M.'N-M. cr
/N\cl
AGt : 7.9 kcaVmol AG* : 22.9 kcaVmol
(d) All of these
L8. Select the response that correctly identifies the number of carbon atoms of each rype of
hybridization in the compound given below
H2C:C-CH-CH:O
sp3 spz sp sp3 sp2 sp
(a)22 0(b) 1 30
(c)03 1 (d) 1 21
19. Circle represents most basi c atoms in these molecule. Which of the following is
representation ?

,rrffi (b)

')
dq
HzN

(c) HzN
(d) A11 of these

20. Circle represent most acidic hydrogens in these molecules. Which of the following is correct
representation ?

MeO2C

(b) HO

(d) All of these

 I

2t.

v ?". R.
Rank the following in decreasing order of their acidic strengths.

rgr
I

H H cHs
(B) (c) (D)
(a)A>C>(3r, (b)A>D>B >C (c) A>D>C>B (d)D>A>C>B
22. a
Cyclopropane
tr
Cyclobutane Cyclopentane
(D (r) (IID
The correct order of heats of combustion of above compounds is :
(a) I>II>III (b)Ir>r>IIr
(c) III>II>I (d)III>I>II

zs.*,X (B)R (c)?

Compare carbon-carbon bond rotation across & B, and C
(a)A>B>C (b)A>C>B
(c)B>A>C (d)B>C>A
24. Which of the following acids would have a STRONGER CONJUGATE BASE ?
(A) HzS vs Hzo

.1*, .i*,
(B) (-\o vs (,
(C) CH3C CH vs CH3CH : CHz
-
(a) 2, 4,6 (b) 1, 3, 5 (c) Z, g, s (d) 1, 3, 6

ffi
O ' tr,o + Hz; (e =c14)

M"j; r.10,.,
Major products of the reaction is (are):
26.
,ro ,0,O.
'yVhich of the following compound is most stable
N'Q ?
(d) both (b)& (c)

,cgHrg FaHrz

(a) (b)

Hv 9qHrq

(c) (d)
AcO AcO

27. Selected bond angles for six hydrocarbons are shown below. Arrange these hvdrocarbons
according to their pKovalues, from the lowest to the highest.
12go

,fl,
4")
H',\l09'50
4<b11so :X:
\-,
ll70 fr*:108.
(r) (r) (m) (nt
1900
{-
H:H ><p,,0"
CV) (u)
(a)V<I<VI<II<III<IV (b)rv<I<II<III<V<VI
(c) II<tV<I<VI<V<III (d)I<V<IV<III<II<VI
28. Which statement about the following equilibrium is true ?

o- K+ + H2o -I-o, I
+ x+os-
t-butoxide pKo : 15.7 pKo : 18
(a) The equilibrium favours the products
(b) t-Butoxide is the dominant anionic species in the equilibrium
(c) Water is the weaker acid
(d) t-Butoxide is stabilized by resonance
29. Consider the following reaction involving two acids shown below : formic acid and HF.
o o
K+F- + ,Ao,
pK": 3.8
+ HAo-r +HF :3.2
PK"
 @ i r',*#.rffi
Which of the foliowing statements about this reaction are true ?

(A) I;ormic acid is the strongest llrons{e,i acid rn the reaction

(B) Hf is the strongest Bronsted acid in the reaction
(C) KF is the strongest Bronsted base in the react-ion
(D) KO2CH is the strongest Bronsteri base in the r"eaction
(E) The equilibrium favours the reactants
(F) The equilibrium favours the products
(G) Formic acid has a rveaker conjugate base
(H) HF has a weaker conjugate base
(a) A, D and F (b) B, D, and H (c) A, C, and H (d) B, D, E and H
30. Which one of the foliou'ing compounds has a dipole moment significantly different from zero?
OH

(a) (b) (c)

CICH2 \ /rCH2Cl (d) fry
HNJ
H

HO NC -a:
c\t
clcH2xcH2cr
z

3L. Which one of the following has the smallest heat of combustion ?

9H,
!",
(a)ll - =
-
(b) (c) .$\./.L J tal
nrr:a' Hsc Hsc I Hs(
C(CH3)3 c(cH3)3 c(cH3)3 c(cH3)3
'92. Rank the following substances in order of lecreasing heat of combustion (maximum *>
minimum].

j*' SHs

CH:
d"' ,rrtl
CH3
1 3 4
(a)1>2>4>3 (b) 3 >4>2>7
(c)2>4>1>3 (d) 1 > 3 > 2> 4
33. Which of the following has lowest pK o value ?

o)e.r€
o ra
"'oAo "'6ft
 t*#Ca{*:"i**i.#il'.l,j:liilil ji.ti.iii,ili]ilr i'i j,;ri'?i $'iit, :.t,.ii:;'i.il i

3,4. Arrange the following (w, x, !, z) in decreasing order o f their boiling points:

q, L) -N-
I

cHs I

H
(w) (x) (Y) (z)

(a)w>x>z>y (b) w >x>y>z

(c) w>z>y>x (d) w >z>x>y
35. Arrange the following in increasing order of their acidic strength.
o^aoo
(i,& ,,,,"5 (m)# ,,ffocH3
(a) III<tr<IV<II G) II<l<IV<III
(c) I<III<IV<II (d)II<III<I<IV
36. How many degrees of unsaturation are there the following compound ?

(a) 6 (b) 7 (c) 10 (d) 11

37, The heat of hydrogenation for 3-methylbutene and 2-pentene are -30 kcal,/mol and -28
kcal,/mol respectively. The heats of combustion of 2-methyibutane and pentane are - 784
kcal./mol and -782 kcal/mol respectively. All the values are given under standard
conditions. Taking into account that combustion of both alkanes give the same products,
what is AH (in kcal/mol) for the following reaction under same conditions ?

z r .

(a)0 G)-+ (c)-2 (d) 2

38. Vfhich of the following o-bonds participate in hyperconjugarion ?

H
cHg

(a) I and II (b) I and V (c) II and V (d) III and IV

.d'
 *1o-,
L(*)
39.

,-HO
((r)
Decreasing order of acidic strength of different (-oH) groups is :
(a)w>x>y>z (b)w>z>x>y (c)z>w>x>y (d)z>x>w>y

w@@
40. Arrange the following alcohols in decreasing order of the ease of ionization under acidic
conditions.

OH OH OH
(r) (rr) (m)
(a) I>III>II (b) I>rI>rrl (c) II>III>I (d)II>I>III
41.

,,,()
42.

o)O+,rm (d)O
Which one of the compounds shown below, is not an isomer of the others
,r ?

43. Arrange the anions (p) eHr, (q) NHz, (r) ou-, (s) F-, in decreasing order of their basic
strength.
(a)p>q.>r>s (b)q>p>r>s (c) r>q>p>s (d)r>p>q>s
One among the following compounds will not give effervescence with sodium carbonate:

-.^.- /so3H Noz Noz

(a) C6H5CO2H *, q (c) c6HsoH (d)

Noz
45. The carbo>rylic acid which has maximum solubility in water is:
(a) phthalic acid (b) succinic acid
(c) malonic acid (d) salicylic acid
46.

o
Among the following compounds, the most basic compound is :

O ,orQ
(a)

H
H ",Q (d)
N
H

47.

Arrange the (C - H) bonds x,y and z in decreasing order of their bond dissociarion energies
in homolysis.
(a)y>x>z (b)z>x>y (c)z>y>x (d)),>z>x
48. 23 g of sodium will react with methyl alcohol to give :
(a) one mole of oxygen b) 22.4 dm 3 of hydrogen gas at NTP
(c) 1 mole of H2 (d) 11.2L of hy'drogen gas at NTP
49. Which of the following is most polar?

,.rfu
o

,rr8

(x) (z)
The correct order of decreasing basic strengths of x, y and a is :

(a)x>y>z (b)x>z>y (c)y>x>z (d)y>z>x

51. Which of the following is the srrongest Bronsted acid ?

NHz OH OH

52.
(a)
",O (c)

Which of the following is the strongest Bronsted base ?

O (d)
O
H H
H

o o
I I

(a) (b) zNl (c) (d)

HH
53. Which of the following is polar aprotic solvent ?
(a) DMSO (b) Crown ether (c) DMG (d) All of these
 Some
(a) CH3COzH and CH2FCO2H
(b) CH2FCO2H and CH2CICO2H
(c) CHzCICO2H and CH2BTCO2H
(d) CH3CH2CHFCO2H and CH3CHFCH2CO2H

55. H-C - C3C: Ci-CHg;

Compare the bond lengths a and b:
(a) a-b (b)c>b (c) b>a (d) o >>> b
56. \rVhich (isomeric) amine has lowest boiling point ?
(a) 10 amine O) 2o amine
(c) 30 amine (d) cannot predict

2sbcls > P;
Pwillbe:

,u@ o)@)2sbcr8

,ro (d) mixture of (a) and (b)

58. Which of the following substances is not an isomer of 3-ethyl 2-methyl pentane ?

(b)

fcl,,l-F I
(d) All are isomers

59. Which of the following is an isomer of compound 1 ?

o
il
cH3cH2cHo CHs
-C-CH3 CHa cHz-cH-cH3
(1) (2) -CH:CH-OH
(3) \o/
(4)
(a) 2 (b) + (c) 2 and 3 (d) all are isomers
Br

60. _sr}- rat ;

which statement is incorrect in respect of the above reaction ?

(a) Product is aromatic (b) Product has high dipole momenr
(c) Product has less resonance energy (d) Product is soluble in polar solvent
61. Some pairs of ions are given below. In which pair, first ion is more stable than second?
@o
(a) CHa andCH3
-CH-CH3 -CH-OCH3
:
(b) CH3
-CHz
o@- 3, -CHs and CH, CH- CHz -3 r,

(c)
Utt'u,ro
cHg cH3 cH3 N
ef* CHg
(d) -gH-
| and - l^ -
cHz
- c@- cH3 cHg
- cu - cH,
62. Among the given pairs in which pair, first compound has higher boiling point than second ?

(a) CHs andCHg CH-CH3

-CH2OCH3 -
OH
(b) CH3 and CH3
-CHz -CHz -CHs -CHz -cc#j_cr,J
l'
(c) CHg andCH3
-CHz -CHz -CHz -CHe -CH-CHz-OH
(d) CH3 and CH3
-CHz -CHz -CHs -CHz -CHz -Cl
63. Which of the following alcohols is the least soluble in water ?

(a) Ethanol (b) 1-Propanol

(c) 1-Butanol (d) l-Pentanol
64. Which of the following alcohols is expected to have a lowest pKo value ?

(a) Ethanol (b) 1-propanol

(c) 2, 2, 2-trifluorethanol (d) 2-chloroethanol
65. Which of the following alkenes is the most stable ?

ro1\ (b) (c)a (d)^(

66. Bond X is made by the overlap of which type of hybridized orbitals ?

(a) sp and sp3 (b) sp and sp2

(c) sp2 and sp3 (d) none of these
67. Increasing order of acidic strength of given compounds is :

OH OH

NC H3CO
(III)
ry"'(IV)
 (a) III<I<IV<II (b)ll<I<tV<III
(c) I<III<[V<II (d)I<III<II<IV
68.@CooH+NaH3o3-_-Co2+@CooNa,tiswiththeproduct:
(a) coz *, (c) both (d) none of these
@cooNa
69. Rank in the order of increasing acidity.

coloH r,,r$**,, (rrr)

Go"
(a) III<l<ll (b) I<III<II
(c) III<ll<I (d) II<I<III
70. Which compound has the highest value of pKo?
(a) Cl CHz CHz COOH (b) cHs
- - - -cHz
CI -cooH
I

(c) CHs CH-COOH (d) CHs C-COOH

- I
- I

CI CI
71. Consider the hydrogen atoms attached to three different carbon atoms (labeled 1, 2 & 3).
Rank the attached hydrogen atomr.r" ot.r from most acidic to least acidic.

(A+o{'
t2
(a)2>1>3 (b) 1>2>3 (c) 2>3>L (d)S>2>l
72. Decreasing order of acidic strengths of following compounds is :

oro (y)o (z)$

(a)x>y>z (b)y > x > z (c)z>y>x (d)z>x>y
73. Among the given pairs, in which pair second compound is more acidic than first ?
o o
lt lt
(a) BTCHzNOz and CH3CH3 (b) CHs C CH2CN and CHs C- CH3
OH
- -
OH OH

(c) &6 (d)Q &

6
CHs-C: O cHs
74. Which of the underlined atoms in the molecules shown below have sp-hybridization ?
(u) GHzCHCH3 (v) CHzGCHCI (w) CHgCHj (x) H-C:C-H
(y) CHgEN (z) (CHg )zCNNHz
(a) x and z (b) x, y, and z (c) u, w and x (d) v, x and y
75. Which of the following, is the product of the reaction benareen AlCl3 and CH3OCH3 ?
CI CI
| - rCHs
di.r, I* d-rcH,
(a) cr
- i-- G) cl - Al*- ics,
CI CI
CI CI

cr-^|,.O (::, l- +
(c) (d) Cl
- 4t - CH3OCH3
I

CI C1

76. Which of the following compounds contain at least one secondary alcohol ?

ffoffi"?+"T*A,ffi*
OH

(D 0D (rrr) (IV) o) or)

(a) I, II, [V, VI (b) I, III (c) I, II, III, V
(d) I, III, V
77.

,rf $)ry
Which of the following has the most negative heat of hydrogenation ?

(oe)- (c)

78. Which of the following options is the correct order of relative stabilities of cations I, II and III
as written below (most stable first) ?
+ cHs

(r)ry." (II) H2C : CH (III)H3C-C-CHz

l*
-CHz -tt -CHs I

cHs
(a) I>II>III (b) lr>III>I (c) III>I>II (d)I>III>II
79. What is the decreasing order of stability (most stable + least stable) of the following
carbocations ?
+
.A+ r\ A A.r* (,
72 5

(a)3>2>1>4>5 (b)g>2>5>4>1
(c) 7=4)2=5>3 (d)3>1=4>2x5
80.
the hydrogen indicated by arrow will be easily removed as :

(a) H* (b) Ho (c) H' (d) H-2

8L. Rank the bond dissociation energies of the bonds indicated with the arrows. (from smallest
to largest).
H
t ?'2
H!/1*zcu'
II
\}fi-'
(a) l<2<3 (b)3<2<1 (c) 2<3<7 (d)3<7<2
82. Rank the following compounds in order of decreasing acid strength (most acidic + least
acidic) .
OH

d.*",6 + o Noz
l2 34
(a) 2>4>1>3 (b) 1>3> 4>2 (c) 3> 1 >2>4 (d) 3> 1 > 4>2
83. Rank the following compounds in order of increasing acidiry (r,veakest acid first).
Noz
oH Hsc

Noz

(a)2<3<1 (b) 3 <7<2 (c) l<2<3 (d)2<1 <3

84. Which of the following phenols has the largest pKo value (i. e., is least acidic) ?

(a).,$on o) orr$o,
(c) (d)ru-cOo'
85.
',t$o'
Among the given sets, which represents the resonating structures ?
-II
ao aa
(a) H-C: N-9: -
and H-O-C:N3
I aa
I
H-9 :
Oa

- N: and H-o-C-N:
(b) C -

:o:
+ il
rr
..- ..
(c)H-C:N-O: and H-C-N:
86. Identify each species in the following equilibrium according to the code :

SA : stronger acid ; SB = strongerbase ; WA : weaker acid ; WB : weakerbase.

The pKo of (CH3 )zNH is 36 ; the pK, of CH3OH is 15.2.

+ (CHs )2 NH *
CH3OH
72
CHs
- O- + CH3
- ,.iH- Cn,
I

H
L2 72 72 l2
(a) WA WB (b) wB wA (c) SA SB (d) SB SA
(e) WA wA
87. The hydrogen bonding is strongest in which one of the following set ?
(a)F-H---F (b)o-H---S (c)S-H---F (d)F-H---o
88. Intermolecular hydrogen bonding is strongest in :

(a) methylamine (b) phenol (c) formaldehyde (d) methanoi

\ o-H (u
gg. H SH
OH
OH
\C

{
Identify most acidic hydrogen in given compound.
(a) a (b) b (c) c (d) d
90. Which of the following compounds would ]'ou expect to be strongest carbon acid ?

,",vo .,,c(
(c) CHr(COrEt), (d) cH3cocH2cooc2Hs
9L. 5-Bromo-2-cyclopropyl cyclohex-2-enol have correct structure is:
Br OH

(a)
HO
_tr ,rrrrff
Br
(c)
OH
92. Rearrange the following in the increasing order of acidic strengtfi.
(i) benzoic acid (ii) p-methorybenzoic acid (iii) o-methyoxybenzoic acid
(a) i<ii<iii (b)iii<i<ii (c)ii<i<iii (d)iii<ii<i
93. In the following acid-base reaction, in which can backward reaction if favoured?
(r) ntoo.@oH=-- o) KH+EIOH =-
go

(c) tuegcoo + H2o (d) + CH3OH = -

=:=
94. Which compound posses highest dipole moment ?
(a) naphthalene (b) phenanthrene
(c) anthracene (d) azulene

es
OtrO -HrO -hO
(E - activation enerry)
Relation benveen activation energies of above reacrions is :

(a)Ez>Er>Ee (b)Es>&>Ez (c) E3>EzrE, (d)E,>Ez>Es

96. Rank the following solvents in decreasing order of abiliry to dissolve given compound.

Solute
(a) EtrO > HrO > EIOH (b) H2O > EIOH > EtrO
(c) HzO > EtrO > EtOH (d) UtrO > ErOH > HzO
:NMe2

97.

""'h*."#i::,]"0
"i;ntn','illtfl
so as (Proton sponge)
Its basic strength is 1010 more than l-dimethyl amino naphthalene.
Reason for high basic strength is :
(a) resonance (b) steric inhibitation of resonance
(c) oftho effect (d) hyperconjugation
 98. In the- given pair o[ compounds, in which pair second compound has higher boiling point
than first compound'?
"

(")[\ oHandLo

(c) HO CHz CH, OH and CH, CHz CHz OH

- - - - - -
CH
T^.3
lruH
cal /il- and
(,
LJ
Me-NaM"
'"-*a'e
ss
+ H:"
NOz
(A) (B)
NOz
. Dipole moments of given compound will be :

(a) (A) = 6.87D, (B) = 4.11D (b) (A) = 4.11 D , (B) : 6.87 D
(c) (A) = 4.11 D, (B) : 4.11 D (d) (A) - 6.87 D, (B) = 6.87 D
1OO. Order of decreasing basic strengths of halides is :

(a) F- > Cl- > I- > Br- (b) F- > Cl- > Br- > I-
(c) I- > Br- > Cl- > F- (d) t- > Cl- > Br- > F-

,,d
1o1. Among the rylenes, which is thermodynamically most stable ?

o,d
(c) (d) All are equally stable

lO2. Heat of combustion of nvo isomer x and y are 17 kJ/mol and L2kJ/mol respectively. From
this information it may be concluded that :
(a) isomer x is 5 kJ /mol more stable
(b) isomer y is 5 kllmol less stable
(c) isomer y has 5 kIlmol more potential energy
(d) isomer x is 5 kIlmol less stable
 least exothermic)

x
--+

(A) (B)
\ (c)

(a) B>A>C (b)A>B>C (c) C>A>B (d)c>B>A

104. rI (2) (3) G)

Choose the statement that best describes given compounds.

(a) 1,3, 4 represent same compound (b) l and 3 are isomer of 2 and 4
(c) 7,4 are isomer of 2 and 3
(d) All the structure represent the same compound
1O5. Decreasing order of acid strengths is :
e
Ph-OH, Ph-cH2 Ph-co2H, Ph-cHr- NHs
(A) (B) -oH, (c) (D)
(a)B>A>C>D (b)C>A>B>D (c)C>A>D>B (d)c>B>A>D
L06. Rank the following in decreasing order of basic strength is :
(A) CH3 C- (B) CH3
-CH, -C - -CHz -S-
(c) cH: cHz co, (D) CH3
- - -CHz -O-

"t
(a) B>A>D>C (b) D>A>B>C (c) A>D>B>C (d) A>D>C>B
1.OZ. Among the given compound choose the rwo that yield same carbocation on ionization.

o,. +
(A)
5" Br
(B) (c) (D)

(a) A, c (b) B, D (c) A, B (d) B, C

L08. Oxalic acid PKr
Malonic acid PKz
Heptanedioic acid PKs
where pKt, pK z, pK z are first ionization constants. Incorrect order is :

(a) pKr > pKz > PKa (b) pKr <pKz < PKe
(c) pKs > pKz > PKr (d) pKs > pKr > PKz
 .,,V
H

HH

Noz cHa
1L0. Dipole moment of which ketone is maximum ?

,,,Y
o

o)
V o
(c)
A (d)ao
L1 1. Correct order of basic strengths of given amines is :
(a) MerNH > MeNH2 > MerN , NHs (Protic solvent)
20 10 3"
(b) Et2NH > Et3H > EINH, > NHa (Protic solvent)
2" 3" 10

(c) Me.N > MerNH > Me-NHz > NHs (Gas phase)
(d) All are correct
T"
\--cH,
112. Order of basic strength Ph
- (A) - (B)
NH2,
-
Ph NH Me Ph -oi-*''
-
Me
d,
(c) (D)
(a) A>B>C>D (b) B>A>C>D (c) C>B>A>D (d) C>B>D>A
 (a) CHs CH (b) CH3
(c) CHs - - CHz CH CH CH,
(d) CH2 - CH'- -
tt
-C -C-CH3
cH3 cH3
-

ll4. Which has maximum dipole moment ?

o
il
C
/\
(a)o (c)
db ,^,6'b
115. (i) Et rN (ii)ffi (iii)ca
Compare the basic srrengths of compounds given:
(a) (i) > (ii) > (iii) o) (ii) > (i) > (iii)
(c) (ii) > (iii) > (i) (d) (iii) > (ii) > (i)
116. For the following rwo reactions, which statement is true ?
J
I
J
J
'l
] ^.
]reactants \
Ptoa'*
Reacnon A

(a) Reaction A is faster and less exergonic than B

(b) Reaction B is faster and more exergonic than A
(c) Reaction A is faster and less endergonic than B
(d) Reaction B is faster and more endergonic than A

tt7. :=5 n* ,

d,/'i
cHs
Idenrify the site, where attack of H*. is most favourable.
(a) a (b) b (c) c (d) d
118. Rank the following l"**.

",@ o,@ .,,OO

alkenes on order of increasing

(a) 1<2<3 (b)1<3<2 (c)2<1<3 (d)2<3<1

119. Which of the following cyclic amine has lowest LG# for inversion ?

ol - n-Bu
)N
t.l - ph
)N -
t-Bu cal
)rv
l2O. Rank in the order of increasing acidic strength:

oo
r,o,.tco,Et
(A)
#t;xr
(B)
"v QO2Et

(c)
(a)A<B<C G)e<c<B
(c)B<A<C (d)B<C<A
121.. Which one of the following dienes would you expect to be the most stable ?

(a) (b) (c) (d)

122. Which metal catalyzed reaction would release the maximum amount of heat per CH, unit ?
(a) cyclopropane +Hz -) propane (b) cyclobutane +Hz -+ butane
(c) ryclopentane + Hz + pentane (d) cyclohexane +Hz -+ hexane
o o o

12g, Or0' ,rr0 (.)0e

o
Compare basic strengths of the above compounds:
(a)A>B>C (b)B>A>C
(c)C>A>B (d)c>B>A
124. On reaction with acid, 4-pyrone gives a very stable cationic product. Which of the following
structures shows the protonation site in that product ?

L}4-Pvrone
o

,.r6 I
H
 Which of the following

A\"
OMe OMe

(a) (b)^t (c)

126. Which carbocation is the most stable ?

r"r# ratS
1,27. Consider a positively charged C2H3 species in which the positively charged carbon is sp-
hybridized. the uncharged carbon is sp'-hybridized and an empty p-orbital is perpendicular
to the ft s\/stem. What it the best description of this cation ?
(a) vinvl (b) allenyl (c) alkyl (d) allyl
L28. Which of the tollowing reactions is not exothermic ?
(a) CH, Cl -'. CHs CHs
- - -----) CHo + CHs
- - CH2 CI
(b) cH3-cl - (cH3)3c-H ---> cHo+ (cH3)3c-cl
(c) CHs-Cl - CH2:CH-CH. ----+ CHo + CH2:CH-CH2-Cl
(d) cH3 cl * cHz : cH2 ---+ CHo + CH2: CHCI
-
129. List the follon-ing carbocations in order of decreasing stabilization energies.

(r)t
(a) II, III, I, [V
rrU
(b) III. n-. il. I
(rrDer
(c) III, IV, I, II
(Mo
(d) I, II, IV, III
L30. For the following rwo acid-base reactions. n'hich statement is true ?

(l) CH3CH; + CH3NHz CH.CH3 = CH3NH-

pKo=35 == ci.. =50

(II) F- + HzO : HF + HO-

pK,:15.7 PI.=32
(a) I is favoured to the right, II is favoured to the left
(b) I is favoured to the left, II is favoured to the right
(c) I is favoured to the right, II is favoured to the right
(d) I is favoured to the left, II is favoured to the left
L3L. Rank the hydrogen atoms (Ho, H6, H. ) in the following molecules according to their acidic
strengths:

(a)c>b>c (b)b>q>'c (c)b>c>a (d)a>c>b

1,32. In which of the follow'ing reactions, baclorvard reaction is favoured ?

(a) H- + Li+ -CH2CH3 + H-C :C :@Li+ + H3C-CHg

{b)
IB3-C-H
,raAou +
-ocH2cH3 {dl + HocH2cH3
= F3c

(c) CHTCH2 S H2 + CHTCHTOH * cHrcH2sH + cHrcH, 3- n

I

H
+
NHz
TN,

133.
(d)
o =o+
Which carbocation is the most stabilized ?

134. Taking into account of h.vbridization and resonance effects, rank the following bonds in
order of decreasing bond length.

,,,,j'/"'
-.P()9,-
(rr)
(a)I>II:lll (b) II>rII>I (c) I>III>II (d)II:III:I
L35. Which one among the follorving carbocations has the longest half-life

,rrry
?

,',OiO
,rw (d)
@
cu.-i<H,
CH:

136. Rank the following alkenes in order of decreasing heats of hydrogenation (largest first)

,/\/ ,,4/ ,,4.

1 34
(a)2>3>4>l (b)2>4>3>1
(c) l--, ll>4>2 (d)1>4>3>2
i:t!,,:,:.

'''#,''''
137.

o)>+ Brr4)-r,. +HBr

hv
@)Y+Br, , *HBr
138.
Yr,

,ranar,

(a,^.,'1n,",1
139. Which one of the following is most stable ?

^(d,m
HHH
,r,q!*-H,.,q$
5
T
(a) H-N*-H (d)

+
H
141. Compare relative stabiliry of the following resonating structure.

#
O-n o

C
(i) (ii) (1ll) c
il C
N ilt ll
N N_
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii)
(c) (i) > (iii) > (ii) (d) (ii) > (iii) > (i)
142. Compare relative stability of the following resonating structure.
o- o o

(p)
/-A I
cHs
(q)/-* I
(r)
.\[
C

lll lll il
N N N_
 ii i:;: :,::!ii,::il:ijltl;iiiai:i:i;i:. :.

(a) p>q>r (b)q>p>r

(c) q>r>p (d)p>r>q
143. Which of the following isomeric hydrocarbons is most acidic ?

(a) (b) (c) (d)

O?
144. Which of the following has the lowest barrier to rotation about the indi cated bond

+
?

(a) (b) cc) (d)

O>z
145. Use the following data to answer the question below.

O+
excess Hc
(AH = -28.6kcal mol-1)

(Ni) (AH = -7L6.2kcal mol-1)

Anthracene
Caiculate the resonance energy of anthracene:
(a) 8+ kcaf mol (b) 100 kcaf mol (c) 110
kcafmol (d) 116 kcafmol
146. How man]' double bond equivalents does a compound of molecular formula C6H12O6
possess?
(a) o o)1
(c) 2 (d) 3
147. How many double bond equivalents does amoxycillin (shown below) possess ?

(a) 5 (b) o
(c) 7 (d) e
148. What is the oxidation state of osmium inTB and 7C, respectively ?
oo o\
,- \orl-- zo
Os
/\
oo o,/ \o
7B 7C
(a) 6, 8 (b) B, 6 (c) 6,6 (d) 8, B
2A

Hb
149.
HC
iHal
HHe
Identify most acidic hydrogen present in the above compound:
(a) a (b) b (c) c (d) d
150. Which of the follorving compounds has most acidic hydrogen ?

(")O-*<l:
H

(.)@*<*:
tl
HH
15L. Acetic acid, (CH3COOH), has apKo of 4.8. Ethanol, (CH3CH2OH), has a pKo of 16.0. What
are the major species present, when acetic acid and ethanol are added to water and the pH is
adjusted to 7.0 ?
(a) CHTCOTH and CHTCO2OH (b) CH3CHTO- and CH3CH2OH
(c) CHTCOTH and CHTCHzO- (d) CH3CO, and CH3CH2OH

1.52.

The most stable canonical structure of given molecule is:

,.r8
153. In the potential energy diagram to the right, the point X represents :

Electronic Reorganization
 s#
(a) a transition state (b) a reaction intermediate
(c) a resonance hybrid (d) a reactant

rs4. p.n,
(r)
p.,, (II) (III)
Which of the following orders is correct for heat of hydrogenation of these compounds ?

(a) I>III>II (b) III>II>I

(c) III>I>II (d) II>I>III
cHg

1.55.
cHs

Which of the following orders is correct for heat of hydrogenation of these compounds ?
(a)I>ll>lII (b)rrr>il>I (c) II>III>I (d)III>I>II
156. CH2 : O <------) = CH2 Oo <----+ 'CH, - O@
-
(r) (II) (m)
Which of these stmcrures is practically not a valid canonical structure for formaldehyde ?

(a) I (b) rr
(c) III (d) None of these
157. CH2 : CH CH : CH 3NH3 :cHr-cH:cH-'cH- tNH,
- - ;

(r) (li)
tcHr-cH:cH-cH:NH:
(rI)
Which of these structures is not a valid canonical structure ?
(a) I (b) II (c) III (d) none of these
o go
L58. /\
il
<--)
tt *t
6G)

H cHz /.yr, /\r,

(r) (II) (m)

The correct order of stability for the given canonical structures is :

(a) I>III>II (b) III>I>II

(c) II>III>I (d) II>I>III

lse.O€O... O
@
(r) (II) 0n)
The most stable canonical structure among the given structure is :

(a) I (b) rr
(c) III (d) all are equally stable
160. *ocH3
(D
ry (r) OCH3
For the given compounds the correct order of resonance energy is
4*, OD
:
(a) III>I>II (b) II>I>III
(c) I>II>III (d)III>rr>r
OH
161. .r,:[- X<t" 1' ,cHs
cHs-E-*i^, CHs -
I : Niar,
C
e ,cHg
-cHg
(I)
-CHg
r,il (Iil)
The correct stability order of the given canonical strucrures is :

(a) I>II>III (b)III>r>tr

(c) I>III>II (d)Ir>rrr>r

162.

In the above compound, how many sites are available for the attack of CH.O- ?

(a) 1 (b) z (c) 3 (d) 4

163. CH2
tCH2 cH3o - cH tt cH, cH3o-cHt' cH-c-oEt
il
(D (II) (rr) o
Which of the following orders of rotation barrier about the C - C bond, as indicated, is
correct ?
(a) I>II>III (b)rrr>II>r
(c) III>l>II (d)II>I>III

!G4.
@cHpcHz @6s-,cr@ (D (II)

(}.6s-,cr@ocH3
(m)
Which of the following orders of rotation barrier about the C : C bond, as indicated, is
correct?
(a) I>II>III (b)ttt>II>I
(c) III>I>II (d)II>I>III
165. Which of the following compound is not resonance stabilized ?

@
A

(a)
ot" (b)
G" (c)
+" (d)
166. Homologous compound have same:
(a) General formula (b) Emperical formula
(c) Structural formula (d) Molecular formula
167. Most acidic is:
OH OH OH

(a)
d ",+cHa
Noz
Noz
tt'+
168. Which of the following substituents will decrease the acidic strength of phenol?
(a) (b)
(c) -NOz
{H, (d) -cN
-cHo
169. Which of the following structures possesses a cross-conjugated system?
(a) CH, :CH-CH:CH-CHz (b) CH2 :CH-C:CHz
I

cH2cH3
(c) CH, :CH-CH-CH:CHz (d) CH2:CH-C:CHz
:
I I

CH: CHz CH CHz

l7O. Examine the following resonating stralctures of formic acid for their individual stability and
then answer the quesrion given below.
oo-o-o+
lll+l*l-
H-C-O <--+ H-C :
H O-H e--+ H-C-O H +------+ H-C-OH
I II III tV
Which of the following arrangements gives the correct order of decreasing stability of the
above-mentioned resonance contributors?
(a) II>I>III>IV (b) I>II>III>IV
(c) IV>III>I>II (d) w >III>I>II
t7l. Which of the following is not resonating structure of each other?
(a) CH, andCHs N
-N -C -S -S -C -
(b) CH3
-A:OandCHs -C -6
o o-
(c)
il
CHr-C-OHandCH3- C :O-H
l*
(d) CH2 :CH-C - Nandi"r-CH:C: N-
172. In the molecule CH3C - CCH : CHr, the maximum number of carbon atoms arranged
linearly is:
(a) 2 (b) g
(c) 4 (d) s
 r,-y rf{,ff.ffi
173. The stabiliry order of the following carbocations is:
+++

,1 o
n /1
I II III IV
(a) II>IV>III>I (b) W>II>III>I
(c) II>III>I>IV (d) I>III>II>IV
174. Total number of cr-hydrogen in given compound is:

(a) 4 (b) (c) 6 (d) 7

1.75. In whi ch pair second ion i s more stable

90
than first?

VVo o
@

ero' ei-"'
(i) (iii) (iv)

(a) (i) and (ii) (b) (ii) and (iii)

(c) (ii) and (iv) (d) (iii) and (iv)
176. \tVhich one is the most stable cation in the following ?
OH OH

(a) o *'.d (c) (d)

d
177. The most reactive amine towards dilute hydrochloric acid is
ilH NHz

,rrd ,r# (d)

O
I
H
178. How many resonance structures are there for anthracene ?

(a) 6 (b) s (c) 4 (d) 2

179. Which base is strong enough to convert (CH, ), COH into (CH, ) 3 CONa in a reaction that goes
to completion ?

(a) NaNH 2 (b) CHTCHTNa

(c) NaOH (d) CH3COTNa
(e) More than one of the above
L80. Based upcn an understanding of product stabiliry, predict the product formed when the
following dianion reacts with one equivalent of atid
oo oo
Z\A HO>

oHoooooHooo ooo
(a)AA- b)AA. (c)A)- (d),.Al\..
o c'o

c.tA,A

ai
\./ A
\-'J -
7234
\l r-
\7
(a) 4<2<1 <3 (b) S<1< 2<4 (c) 1<3 <4<2 (d) 2 <4<3<1
L82. Among the given cations, the most stable carbonium ion is ?

sec-buryl
(a) (b) tert-buryl (c) n-buryl (d) None of these
L83. Cyclohexadiene contains vinylic and _ allylic hydrogen atoms ?

1)
\:/-.
(a) 2 and 2 respectively (b) + and 4 respectively
(c) 2 and 4 respectiveiy (C) + and 2 respectively
34

1. (c) 2. (d) 3. (d) 4. (a) D. (d) 6. (d) 7. (b) 8. (c)

9. (b) 1.O (c) 1L. (b) 12 (b) 13 (a) !4 (b) L5 (b) L6 (b)

t7 (d) 19. (c) 19. (d) 20 (d) 21 (c) 22 (c) 23 (c) 24 (a)

25 (d) 26. (d) 27. (d) 28 (a) 29 (d) 30 (a) 31 (c) 32 (c)

33 (d) 34 (d) 35. (d) 36. (d) 37 (b) 38 (b) 39 (a) 40 (c)

4L (c) 42 (d) 43. (a) 44. (c) 45. (c) 46. (d) 47 (b) 48 (d)

49 (b) 5(} (b) 5L. (d) 52. (d) 53 (d) 54 (a) 55 (c) 55. (c)

o/ (b) 58 (b) 59. (d) 60 (c) 61 (b) 62 (b) 63 (d) 64 (c)

6s. (d) 66, (c) 67. (a) 69. (a) 69 (d) 70 (b) 7l (a) 72 (d)

73. (d) 74. (d) 75. (a) 76. (d) 77 (a) 7A (a) 79 (b) 80 (a)

8L (d) 82 (d) 83. (d) 84. (c) 85. (b) 86. (a) fJ7. (a) 88. (b)

89. (a) 90. (d) 91. (b) 92. (c) 93. (d) 94. (d) 95. (d) 96. (d)

97. (b) 98. (d) 99. (a) 100. (b) lo1. (b) 102. (d) 103. (a) L04. (a)

105. (c) L06. (c) 1.O7. (c) 108. (b) 109. (c) 110. (c) 1_L 1. (d) tLz. (c)

113. (c) L14. (c) 1L5. (c) L 16. (a) ll7. (a) 1L8. (d) L1g. (c) Lzo. (c)

,,2l. (c) t22, (a) 123. (c) 124. (c) 125. (d) 7.26. (b) 127. (a) 128. (d)
129. (b) 130. (a) 131. (c) \32. (d) 133. (c) 134. (d) 135. (a) 136. (d)
137. (c) 139. (d) 139. (c) 140, (c) 141. (a) 142. (d) 14S. (b) 144. (c)
145. (a) 146. (b) 147. (d) t 48. (b) 149. (a) 150. (b) L51. (d) 152. (b)

153. (a) L54. (a) 155. (c) 156. (c) 157. (c) 158. (b) L59. (c) 160. (c)

161. (b) 162, (c) 163. (a) L64, (a) 16s. (c) L66. (a) 167. (d) 168 (c)

L69. (d) 17a. (b) 17l. (a) 172. (c) l7B. (c) 174, (c) 175. (b) !76. (b)
177. 178. 1go, (d)
(c) (c)
:1rl (e) 1g 1. (c) 182. (b) L83. (b)
1. Rank in order of radical stability (1 : most stable).

(a) o ,rrd ,.,Oao (d)tr

2. Predict the acidity order for the three phenols shown below :

Acidiry order : 1 (most) to 3 (least)

(c)

OH OH OH

,r,o'*$-" ,.,[}
(A)

+
Noz Noz cHs

h
OH OH OH

(F)
\,/
I

zcx.
O. CH
 L# li#ft#
i r ! i I ii: : i ii : i !r: 'i I
' r . ,

ffilii ffirri
A. Which of the phenol derivatives above is the strongest acid ?

I Compound A I Compound B tr Compound C

I Compound D I Compound E I Compound F
B. Which of the phenol derivatives above is the weakest acid ?

I Compound A n Compound B t-l Compound C

I Compound D tr Compound E Ll Compound F
C. Which of the mono-nitrophenol derivatives above is the strongest acid ?

tl Compound A - Compound D
D. Which of the carbon-substituted phenol derivatives above is the strongest acid ?

I Compound C I Compound F

4, The following questions refer to the twelve compounds given below. You may enter as many
as six choices in each answer box.

O
G
A. Which compound may serve only as H-bond acceptors ?
a"a
B. Which mav serye both as H-bond donors and acceptors?
C. Which compounds will not participate in H-bonding ?

5. Consider the following compounds and answer A and B.

(rr)clo
A. Which of the compounds is the strongest Bronsted acid ?

(a) I (b) rr (c) III (d) IV

B. \tVhich of the compounds is the strongest Lewis base ?

(a) I (b) II (c) III (d) IV

6. R.ank the non-bonding electrons indicated by the arrows in order of increasing energy.

7. In each of the following sections four nitrogen containing compounds are listed. In the box
under each formula write a number (1 to 4 ndicatins the order of base stren

(h) L--./* - cHs ozN

o
AN-H NHz A
I N_H
fb) (/ ozN NHz
Y o

4ru-H
N(cHrz (.\_H
I N-H
[#I
V H
I U*-cHs

HsC.. 4N-H
fdl H"C/)-c: N
v
I N-H (,
8. For the two sets of acids shown below, rank their acidity most acidic to least acidic.

oo
ll
ffoH ffi,
il

er^.) {,/
(ii0 (iv)

oo o

*,"-f" iA"'(i) (ii)

T,iA",
Br
(iii)
Br
(iv)

9. In each of the following sections four compounds are listed. In the box under each formula
enrer a number (1 to 4) indicating the order of acid strength (1 is strongest & 4 is weakest).

l CHTCH.CU.COTH I CHgCHZCHBTCOzH ClCHfHlCHrCo2H

r-
I CH"CCI.C0"H l

(a) I
IJlAI

l I

C6HSCHIOH C6H5CO2H c6HpcH3 c6HpH

i&)

(e) j" ,n
oo
\-/

ln-H
(d) U*-cHg Go
L0. In the two questions be1ow, you are asked to rank the relative strengths of illustrated acids
and bases. Use your knowledge of resonance and inductive to answer this.
A. For the series of bases shown below, rank the set from strongest to weakest.

(i)

(a)
re
(b) (c) (d)
Strongest

Weakest

0
Strongest

(ii)
OIv{e O
(c) (d) Weakest
__91 _
(b)

B. For the series oi acics shour belorv, rank the set from strongest to weakest.

S trongesl

(i)
-O
(a) (b) (c) (d) Weakest

Stronge

(ii)
HO2C noraD HO2C

OMe

(a) (b) (c) (d) Weakest

1L. In each of the following sections four compounds are listed. (Decreasing order of acidic
strength, 1 is strongest & 4 is weakest).

CH2(C02C zH)z I CH3COCH (CH3CO)2CH2

RCH2NO2

CH2(C :: N)2
ffi ifilx.# r&h,{#

($ o., fr
\r'"cHz
,l,iii,:iri;

12. Rank in the order of increasing basic strength.

NH,

A. (a)
.n
t'
*,J5" (c)A H

B. (a) -N/
O
H

*'tr*O (c) -r(

<)
H

(d)
/
H
p
./
H H H [{
N N/ N/ N/
il
C. (a) il
O) zcr
il il l]

/-\c (c)
,cr (d)
zcr
HzN NHz HzN CHg HzN OH HsC CFI3

13. Compare acidic strength of the following (Write your answer in box).
$#f, i,o"+ i€ ,I$E

L4. Arrange the hydrogens in increasing order of their acidic strengths.

A. "';4 B FF

:,xk-Ha
HU..rrffiH
rlu o-H. \,, HA H
 cHg

{..d'
[l
I
cHs cHs

co2H
l.limonene 2. muscone 3. hicotine 4. ibuprofen 5. camphor

"Y o CHa

Ano' -"
l" Hgc

pr"
+ o-H
6. vanillin
o-cH3 d"', ,.)"r.
H.cAo
7. aspirin 8. goraniol 9. acetaminophenol

l^&ich have carbon-carbon double bonds ?

Which have a ketone carbonyl group ?

Which have an aldehlde carbonyl group ?

Which have aromatic rings ?

Which have a hydroxy group ?

Which have ether groups ?

Which have an ester group ?

Which have an amide group ?

l{hich have a carboxylic acid gqoup:?

; ii ,,€xff :iiiili

16.
ArShte#i A iliiiit .H fl

t
o ocH3
cH2oH

o
_J< N-H
3 I N- H
t-7.t-cHs
\ o
H HCI
H
I
lcl
ll
I

4 C.
| -co2H c02H f -corH

A.
H

Which is the strongest acid in 1?

H
Pi-"::
(a) A (b) B (c) c (d) D
B. Which is weakest acid in 1 ?
(a) A (b) B (c) c (d) D
c. Which is the strongest acid in 2 ?
(a) A (b) B (c) c (d) D
D. Which is weakest acid in 2 ?

(a) A (b) B (c) c (d) D

E. Which is the strongest acid in 3 ?
(a) A (b) B (c) c (d) D
F. Which is weakest acid in 3 ?
(a) A (b) B (c) c (d) D
G. Which is the strongest acid in 4 ?

(a) A (b) B (c) c (d) D

H. Which is weakest acid in 4 ?

(a)A G)n (c) c (d) D

'L7. For each of the six structural formulae (A through F), short'n below', five questions are posed.
The answer to each is a number that should be entered in the a riate answer box.

Q cHz

CH.

ar\ lo
l"
I
SV N- HcC:CH-C.
H

+",
-
\-C-N /N-CH3
Hec
H,CACH,

(i) \umber of sp3 carbons : B. Number of sp3 C. Number of sp3

carbons : .................. carbons : ............
(ii) Number of spl carbons : Number of sp2 carbons : Number of sp2 carbons :

(iii);;;;.. or sp carbons : Number of sp carbons : Number of sp carbons :

(iv) Number of carbon-carbon *tt-O.r .urbon-.arbon il;;; ;r carbon-carbon

o -bonds : ...............
(v) Number of n-bonds to
carbon : ............
D. (i) Nurnber of sp3 carbons
"f
o -bonds : ................. o-bonds : ..................
Number of n-bonds to Number of n-bonds to
carbon : .................... carbon :..............
: E. Number of sp3 F" Nurnber of sp3 carbons :

carbons : ...............
(ii) Number of sp2 carbons : Number of sp2 Number of sp2
carbons : ............... carbons : ...............
(iiD ;;;i.. "t
sp carbons : Number of sp carbons : Number of sp carbons :

(i,z) Number of carbon-carbon Number of carbon-carbon Number of carbon-carbon

o-bonds : ............... o -bonds : ............... o -bonds : ...............
(v) Number of n-bonds to Number of ru-bonds to Number of n-bonds to
car:bon : ............... carbon :............... carbon :...............
 '(11) pur (1) uurnlor erft rIrtEI tr .6I

(xpr1etrtr1) '(11) pue (1) uurnloa eq] qrletril .gI

,tulsl'ffslrs fl.{J 'l
46. ,,
' '" ffii.#ft$ffi 4ffffi
,,.'.,,,,,"'.': ''".'
iiliiiiiriiiri:iii:iliiiii11i1iliir,iiii
iiii:ii;ii1iii1+ii1!iil*f1i*ii1
iiX+i'+riilii,i 1
20. The junctures centred on atoms A, B and C on the given structure.
. .
,-,()

ab abB
II

A. Which juncture has the greatest deviation from planariry ?

(a) A (b) B (c) c (d) Cannotbeprediaed

B. Of thecarbon-carbonbonds, (shownabove) numberedfrom lto4,whichrepresentthemost
favourable site for H, addition ?

(a) 1 (b) 2 (c) 3 (d) +

21. Select the most stable structure in each of the foll

ar\3
q61 (c)fl*.\,2 {il*.r\rt

(b)H#-C -CH*CH2-CHg
(c) HsC CH .':" C : CH (d)H29 :CH-CHz-CH:CHz
- CH3
-
22. Match the column I and II. (Matrix)

Dipole (crs > rrans)

Boiling point (cis > rraru)

24 . rdentify the most stable structure in each of the followins :

* rffi;;li',lr.;,''. .1,',..''.,',,'iliii; r,ll: 1, :#lttiii figiffi$$ffi

CHs\ + CH.r . H.
(a) -c-H
cHr/ (c) I)\H (d) ;
I

H/ H/ \\H
rart (3)
H\+ cHr-. *
(u)H r:>r_f,<: (b) H/c\f,:
caH
\H
H./
cHsr+ H:.+
CHZ
@)
cnr.rt)a:
(d) H ./C -T:
- cHz
H./ cHs

F;ffii.tSI

(a) (b)

,P.ortffiiiffi
a
(a) ',
(c)
(d)

S*ffi fffiIir:.

cHs\
,.cHg\^ c\
(a) ^./H (b) ^:
L ^/cH,
H./c - cH, H'/ "-,

H\ cH2- cH3 H\^

(.) c ,/cHz-
-\H ^/H
H'/- -
td)
cHr/L - "-n
Fmt (S,)

(d)

(a)
ffia",
 .r-TT:if Tfl :,XI
#
.--rlif

',tGI,,,,.,,,.

HH
H

-". H
(d)
G)n H
H
H

25. Identify the most basic compound in the following.

Part (A)

o NH

, An,
i(o)l
!
I
,ullxn I (c) (d)
ruHANH
l, I

P*rt (B)
NH CH"
-
l"
,.ro
fart (€D

(d) NaNH2
(a) NaOH [b) NaOOCCI{3 (c) ITIaOCH3

Part {D}

0.,
i
i

L**.
GENERAI, ORGAAIIC CHEMISTRY ii#*
26, Identify the most acidic hydrogen containing compound from the following.

, Part (A)

Part (B)

o (ob

,rr&"
5 o
il
C-O-Et

Part (C)
OH OH
oHi
ti
OH I
I
I
I

rbr t9 ,orA
"V\*o,
l

t
(a)

+ cHz cHs
I
I
Noz
I
I
I
NH-
i

oo
G)
oo
[l
*, ll_
.,4 o
(o)AoA

OH

oI-::-*,,'l*,or-x-o*' d .o,Q]acH2oH
 ffiffi#i:#

n1
ZUH
N:C1-C2- I
\l^ -CHz- Cr-H

Give the type of hybridization present at each atom.

(i) N (ii) cr
(iv) Q
-....... (v) CHz
 iifrfie 'G*ffi:ilffi
28. 'lii+lii#,ltii
Predict the direction of the following equilibrium. Write your answer in the box given.below.

(a)o(: n- Br-
CBr <*
@
+Ph3
L,f " + ph3cH

(A) (B) (D)

,o,p*. +cH4 + o-
rcH, I I

29. Match the column I and II. (Matrix)

NaHCO3 will react with

Squaric acid

Na will react with

NaOH will react with

l,a ll
(dl lNaNH2 will react with (s) I(Ols-o-H
l\=/ ll

30. Match the column I and fI.

H3
-CO2H
@
(CH3)3NCHTCO2H

@
(CH:)s N(CH2)4CO2H

(dl zc _cHz co
lo - 2H
d*$or;", ,t::. .,., '' "" r

31. Match the column I and II.

o
lt
c-o-H+NaHCO3--?
74

o
ll
C-O-H +
74
NaHCO3-----+

o
il
C-O-H+Na ----)

(dllG il
S-O-H+NaNH2---)
1t

so3H
+ (B) NuHCo.
={rH-qq *(A)
32. > (C) + (D)
gas gas

I
C
ill
CH

Sum of molecular mass of gas (A + C) is :

(a) 88 O) qo (c) 92 (d) +o
o
il
33. Ph-c *o H NaHCoe r(A) gas
-
Ph * C CH N? >(B) gAS
-
ph _ OH NINH, >(C) gas

R-o-H *u' ,(D)gas

Sum of molecular mass of gas A + B+C + D is :
 +

34. Match the column I and II.

MoIe Rotatibn alr fr eb enbf$,, $. h ter,

180 k{mol

ffiI 88.3 k/mol

q^ L: C
H
Negative barrier
H'/ -/ \.
t.nI
It
ITII
)t
\,
l\-/t
s#

35. Consider the following reaction of boron trifluoride (BF3) and acetone :

:o:

cHt-It -cHs
BFg + Product

A. What is the critical HOMO (nucleophile) of this reaction ?

(a) non-bonding orbital on boron (b) o-orbital of acetone

(c) n-orbital of acetone (d) non-bonding electron pair orbital on oxygen
B. What is the critical LUMO (electrophile) of the reaction ?

(a) p-orbital of BF, (b) o-orbital of BF,

(c) n " orbital of acetone (d) non-bonding electron pair orbital on oxygen
Which of the following is the correct product of this reaction ?

(Lone electron pairs are not shown explicitly).

o6"BF3 @
60

t"A-"'
to-BFs
tu' (b)
og''BFe
(d) /+\
I

.rrA.r, BF"
or

36. Rank the following carbocations according to stabiliry (1 : most stable, 5 - least stable).

AA ,<,,|-A\A\+ dcH"

l.t]trtr
l-lrt
-'^rA-
Etr +

Put the answer in the boxes.

ttEttftr
37. Among the given molecules, identify aromatic, anti-aromatic and non-aromatic molecules.

(1)a rzt 9:
(3) /-\
/\ H
.,\E
(-,[].

," []" (6)E (?)[J G)|i1)

n
o
(e)n
@

(10) (I1)
U (12) I=
otgro
I
E[

(13)
o-r'o
I
(14)
u {rs)
r.a-.--
illl
illt
\o/
(16)
lr
\s/
-
il

H @

qJ Q (1r)Q
Q
(17) (18) (20)

I
H
o

o
o
,
{2t1 ilrl
\o/
-
(rao {23)

A o

ffi fi
Q

(2s) lt
\o/ ll (26) (27) .,*,c)
l[ , :
l'
H,
,:,,, H

(2e) dl
\/,N
(30)
ffi Gzrft*
* ' i''.' fr'.
eaffi
'1',' 0. .

1331 ruenft-H I I
(s+) ia,-"
,-.t
(36)
:'i' oR6 tr,,ffieffiffigotr:rl{,!8ffi

t'
CH,

-Bt
(3e)w
{37) (38) (_} (40)
Q
H
I

N-N
/\
(41)I'.G, (42)Ui (43)
n-N\*/ Y
(44) /-\

A
/-\

,-rrB ,ou,n{:}-n,0,,@
\N/
H
I

Borazole
(48)
@ o

(4e)@,ro,ffn' (s1)

o
o

i"rfi-[l ,,,, \ ,rr* ,rrrfr

LI
o N-t' cH,

,'.,n ,rreO,*,ffi,r,m"
ll /la
-,^.- /l-^-

..4.' A,
til []
,u0,ffi(61)00 (.,)m
UU
,.,,€& ,u,p,urOr
6+,
-. oo
.GEIV.E ,,O$# ,,GXLflts ERY
38. Among the given pairs, which is more reactive towards AgNO3 (or) toward hydrolysis.
t,,
I
I
I
i
j
l
Comslo nd.i'dffi
I

1.

,)

J.

4.

i6. cFI3 -O -CH2 *Cl cHs -cHz -cH2 *cl

7.

i8.
I

I
I

9"
 58

10. n
II
\-/
CI
I

d'' I

39. Put the answer in boxes given as directed.

N ,bf'
,,:a
'
::tl

filice
$$b
:,.: :

$,No. Property ,#dspffi*i:

ffi*wer , effir
' ,, ,*hG..,
property

ro
highest boiling
o' clNH2
li point NCl3 NH4C1 NH,

highest boiling
B.
point

most soluble
C.
in water

highest
lNHlNn
D. solubility in
benzene
VV
^...
:@-re

40. Circle conjugated rtions of these molecules.

 l* ,
.f,:,i,,' ,,,

41.. Arrange in the order as directed -

A. The given alkenes in the order of their stability (1- most stable, 3-least stable).

6.
tf
d#
[J' '

''ffi,,
B. Arrange the following in the order of their acidic strength (1-most acidic, 4-least acidic)

\1r'oH rc {
t: /c
:[]I
'E
tf
i

t:]
A
',8

C. Arrange the following molecules in order of expected boiling point. (l-highest bpt;
4-lowest bpt.)

4, L
nnnfl * l";
:

#d#5
D. Arrange the following alkenes in order of their stability. (1 most stable ; 5 : least stable).

tl tl tl
A B C D

IJ
50 g&ffiffi:rcfrH ffi, r-ffi
42. Match the column. (Matrix)

ComFound$ HuffiGr af.Ben lt*,,hfd*o en

(a)

(b)

(c)

43. Identify (+M) mesomeric & (-M) group of following.

*Hl *M -I *[
 Gmfif# .'O- fiG;lulfiG cHEMISrRIr 6,il

io
I

iil il
, q-NH-CHs

6 o
C_CH"
l"
o Noz

6
d CH:O

O: C-OH

NH - CH3

44. Identify the following solvents as polar protic (PP), polar aprotic (PA), non-polar proric
(NPP) or non-poiar aprotic (NPA).

??(Y
,i. ,t.*r, V ,A*-
o

Dl
EIt] fl
45. Identify the stronger nucleophile in each pair.

(i,-...QQ (ii) o*
(M NHs CH+
AB
46. Encircle the molecule as directed :
(a) Which has higher boiling point : HBr or HCI
(b) Which has a higher boiling point : CH3 - CHz - OH or CHs - CH : O
(c) Which is more miscible with methanol (CH3OH) : CH3 -CHz -CHz -CHz - CH,

or CHs - CHz - CHz - CHz - CH2 - CH3

(d) Which has a higher melting point : CHa or CH3 - CHz - CHg
CH"
(e) Which has a higher boiling point : CH3 -CHz -CHz -CHz - CH, or
l"
CH.-CH,-CH"
47. Encircle the molecule as directed : 'rz\)
(a) Which is more stable : BH3 or BF3 cHs

(b) Which is a stronger base : HO- or H2O

(c) Which is a stronger base : HO- or HS-
(d) acid : HCI or HI
\tvhich is a stronger
(e) Which is a stronger acid : HOCI or HCI
48. Explain why A has lower boiling point than B ?

F3C-CF2 $Fs e
L1 ---L

(A).,, 1. , {B)
*
,

b.p' = ss$c b.p. 67oc

49. Arrange the protons shown in the decreasing order of their approximate bond energies.
qryW:,o.fi €rrffiffrsrnY , .ffi,,'.1, 'i'llLx . ;:;i" r', ij"'l'f'',r, rt,
,.," ,
,6,S

50. Consider the H-atoms in the molecule given below and answer the following.

H6 He Ha

(A) Identify the type (1o, 2" or 3o alkyl, vinyl, allyl etc.) of these H-atoms.
(B) Arrange them in the decreasing order of their case of abstraction (easiest first)
5L. Consider the molecule shown below and answer with respect to Hu # H"

(A) Identify the type of H-atom (1o,2",3" alkyl, vinyl or allyl)

(B) Arrange them in decreasing order of their bond energy.
52. Rank the following carbocations in order of stability (1 - most stable).

AA 2a lco

$
r r,on [ 13o
til
r r Ll^^
\,/z'
tt
\.r'z"
ff tf C

fl
D
B:

##)'-l
53. Rank the following alkenes according to energy (1 lowest energy).

0o0o
ABCD
[]flErl :i
 O,ftSd#{G :,(j',It*r is{ry for" fJsxd,ffi
::i.ii:. !.: : :l:irrli:i:iir,t::.:rj:itil:r!:i:;r:arir::ai:L:iri,]a;'.

Match the column:

GE,IV.ERAI, ORGAIWG

SI,BJECTIVE PROBTEITS

1.. How many 2o carbon in the following ?

G* ^rO
v:u:'-o
2. Find out the double bond equivalent (DBE) value of the given following compound:

3" Total number of functional groups present in the given following compound :

4.
d" o

Total number of o-hydrogen in the given following compound is:

 in the given following compouhd?

6. Total number of DBE value in ;

d..,
7. How many isomers of CaH19O reacts with Na metal to evolve H2 gas ? (eicluding
stereoisomer)
8.

lxl-crown;pl-ether.
valueof
x+Y
=?
3

9. Whichof thegivenfollowingcompoundwillreactwithNaHCO3 orsolubleinNaHCO3 ?

*,O ,oO
il
OH

,nL-,
-\

OH
I

(d) (e), Gn3 '.''* C :CFI

 How many compound are stable after deprotonation ?

2N
,rrA N,A r*r:fi, ;j,

,oQ (0 o
,o

OH
NHz

Sum of n?es of funcrional group and DBE value for given compound is X so the value of
X-10is
12. P = Number of anti-aromatic compound, so the value of x is :

Q =
llll
-N
-N d
Total number of resonating structures of carbonate ion tCO!- 3
0
R = Number of cr-hydrogen in given carbocation

s =Total number of geometrical isomers of CH3 CH-CH CHz

-CH:
T = Number of compound more acidic then CH3CH2OH -

, cH3so3H
6 +,CH3cooH
Noz
Sum of (P +Q + R + S +T) -15is :
13. x =rurrber of (+M)group attached with phenyl ring, so,the,valie of,xls,

NHe

,rrffio*
o
II
Noz
(d)
ryc*Hg
ocH3
(0
ONH-cH3
o o
il II

*,@r* (h) gC-H

1. a-4;b-3;c-2;d-1
2. a-3;b-2; c- 1
3. A-b;B-e;C-a;D-b
4. A- &, c,f, g,k, i; B -b, d, h, j; C - e, i
5. A-d;B-a
6. C<B<A
7, a-2,1,4,3;b- 1, 2,3,4; c-3, 4,L,2;d-3, 2, 4,1
8. a-iv > ii > i > iii; b-iii > iv > i > ii
g. t- 4,2,3, l; b - 3, 7, 4,2; c-2,t,3, 4; d-2,3, 4, L
10. A(i)-d>b> c> a; (ii)-c> a>b > d
B(i)-c>d>b>a; (ii) -b > d > c > a

1L. (a)32r4; G)2743; (c)3124; (d)34L2

1.2. A-c < a < b; B-b < a < c < d; C-d < b < c < a
I"3. A-c < a < b; B-a < b < c; C-c < b < a;D-d < c < a <b;E-c < a <b;F-a >b > c
14. A-H. (Hu <H6;B-H6 <Hc <Hu <Hu
15. A-1, 3,4,6,7,8,9;B-2,5; C-6; D- 3,4,6,7,9;E-6,8,9; F-6; G-7;H-9;I-4,7
16. A-b; B -a; C -d; D -b; E-a; F - d; G-d; H- a
17. (i) (iil (iii) (iv) (v)

A640102
80729 6

c5105 1

D1313 4
E2302 2

F1000 10 0

1.8. a-q; b-p, r; c-P, s; d-q

19. a-p;b-r;c-s;d-q
20.. A-c;B-d
21.. A-b;B-b;C-a
22. o-p, s; b-Q, ri C-9, si d-P, t
23. z-p, r, s; b- Q, ri c-9, t;d- P, r, s
24. A-b; B-c; C-a; D-c; E-a; F-b; G-d
25. A-d;B-a;C-d;D-c
26. A-c; B-b; C-b; D-b; E-b; F-a; G-b; H-c; I-b
27. i.-tp; ii-sp; iii-sp2; iv- tp2;u-sp3;vi-sp3
28. a-forward b-backward
29. a-p. q, s; b-p, Q, r, s; c-p,9, r, s; d-p, g, r, S
30. a-s;b-r; c-q;d-p
31. a-r:'b-q; c-s; d-p
32. b
33. 65
34. a-q;b-r; c-s; d-p
35. A-d;B-a;C-a
36. A -3; B-1;C-5; D-ZE-4
37. Aromatic- 3,4,5,9,12,13, 15, 16, 77,19,22,24,25,26 ,27,28,29,31,32,33,34,35,37,
38, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49,50, 51 , 53, 54, 56, 57,58, 61, 62, 63, 66
Non-aromatic- I, 6, 7, B, 18, 20, 23,30, 40, 55, 64, 65
Anti-aromatic- 2, lO, Ll, 14,27,36,52, 59, 60
38. 1 -B; 2-A;3-B; 4-A;5-A; 6-A; 7 -B;8-B; 9-A;10-A

39. A. NH4CI, cation-anion interactoin - van der waals'forces

.G: , H-bonding (Also dipole-dipole)

GcH3,

v
, 14*11, Aromatic stacking

4r. A. A-eB-ZC-1, B. A -1, B-A C-ZD-4

c. A -3, B-1, C-+D-2 D. A-1,8-ZC-3,D-4
42. a-s; b-r;c-q;d-p
(1)
o
o
(2)
G
oo
C_\H-CHS

,rrd
o
ll
C_CH"
l"
,-,o
Noz

,rro
OCH"
l"
,.,o
CH:O

,rro
O: C-OH

(B)
fi!{t
,'&

(e) X

44. A -PA; B-PP; C -NPA; D-PA 45" (i) B, (ii) B, (iii) B, (iv) A

46. rul@; rrl@, C.l ;

(d)

47. rul@; rui@; r.l@; r.l@

48. In A, highly electronegative F-atoms are present at the periphery. In liquid term these
F-atoms will repel each other due to partial negative charge and thus A rn ill have lower b.pt.
49. Hd >Ha >Hu rH.
50. A- Ha =1' alkyl; Hb = 2'alkyl; H. =2" allyl; Hd =vinyl; H" = 3' allyl
B- Easiest to abstract: H" ) H. ) H5 > Hu Ha Hardest to abstract
"
51. A- Hu =2" alkyl; Hb =2'allyl; H. = vinyli Hd = 3' allyl; H" : 1' alkyl
B-H. )H" )H, >H5 >H6
52. A-2; B-1; C-3,D- 4
5,4. a-r; b-t; c-t; d-s

Subjective Problems
l. 27 2. 17. 3. 3 4.6 5. 4 6. 13 7.4 8.7
9. 2 (c, d) 10. 3 (a, c,0 l1-.7
12. P:3,Q:3,R =7,5 =2,7 =4:19-75=4 13. 4
 replace H, with D and H6 with H
CH"
H,-#Hu
1' ,#t.
I
replace H6 with D and Hu with
cHs
(n
Relation between (X) and ()/) is :

(a) enantiomers (b) diastereomers

(c) E and Z isomer (d) constitutionai isomer
2. Which of the following cyclopentane derivative is optically inactive ?

(a)ffi, OH
,.rffi'
3. Which is the most stable conformer along the 2, 3 C - C bond axis of the compound ?

cHg

(a)
cHs

4. Assign double bond configurations to the following :

NC

H2N - H2C
(a) E b)z (c) E, E (d) Z, Z
5. Allegra, a common prescription drug with the structure shown below, is given for the
treatrnent of seasonal allergies. How many stereogenic carbon does Allegra possess ?

g,,ICOOH
cHe

(a) 1 (b) 2 (c) 3 (d)

6. How many meso isomers of CoHrCl, will be ?
(a) o (b) 1 (c) 2 (d)
7. The stable form of rrans-l, 4-dimethylcyclohexane is renresel;d

gHeJJ
(a)
\s" ,-) o)
\v) p
f
nu
vrr3 -A-r/ CHg
cHs
t---.-..
G)'r'vffrr, (d) \-\ I
CH
 sirP.iffi r^riie:&)}ff.?nHrti.rr,fi t*Snai6$Ir.*ffiffi.$4f.*$&ffifr ffi&1ffi
8. which of the following compound is non-resovable (meso) compounds
?
OH
Br
OH Br
(.)€) (b) (c) (d) AII of these

9. HO-CHr-cH2-F
(2) (3)
which conformer of above compound is most stable across c2
(a) staggered -c3?
eclipsed (partiatiy) G)
(c) gauche (d) fully eclipsed
10. The following molecule is fluorometholone, a steroidal anti-inflammatory
agent. How many
stereogenic centers does it contain ?

fluorometholone

(a) 5 (b) 6 (c) 7 (d) s

How many chiral carbons are there in Reserpine (an antipsychotic
drug) ?

(a) 9 (b) 8 (c) 7 (d) 6

12. How many chiral centers are in the following compound ?

(a) 4 (b) s (c) 6 (d) z

13. Among the following, the optically inactive compound is:
o
il

(a) HsCHr.€
Hsc ",Q]/s\cHs
76

14. :-
traces of base
(A) ; Unknown compound (A) is :
=
xL4
(C : C)
o OH

t*o
,rr(, ,,,U (c) (d)

15. Which of the following compounds might be useful to the chemist trylng to increase the
optical purity of the (d) sample ?
Hoz9

(b)
,.'ryco2H

(o)er'
16. Which of the following molecules is (are) chiral ?

i?,<:, (D
cH(cH3)2 ?l

0r)
H
(Iy)

o
tvj M)
(a) I and II (b) III and IV (c) II, IV and M (d) I, II, ilI and M
17. The structure of (S)-2-fluorobutane is best represented by :
F
E\
^C-H
o) H3cY
I

(a) CH, C HCH2CH3

cH2cH3

t
,r. ""f
F
(c) (d)
cH2cH3
cH2cH3
18. How are the following compounds related ?

,K* H
CH,

(a) Diastereomers (b) Enantiomers

(c) Meso compounds (d) Identical
1.9. Which one of the following is chiral ?
(a) 1, 1-Dibromo-1-chloropropane tb) 1, 3-Dibromo-1-chloropropane
(c) 1, 1-Dibromo-3-chloropropane (d) 1, 3-Dibromo-2-chloropropane
20. Among the following, the Newmann projections of meso-2, 3-butanediol are :
Me Me Me Me
HO Me Me

HO
Me Me
P a
(a) P, Q G) P,R
21. The binaphthol (Bnp) is:

(a) an optically active compound having chiral centre

(b) an optically inactive compound
(c) a meso compound
(d) an optically active compound without having chiral centre
 Which of the following pairs of compounds is a pair of enantiomers ?
!r \
@a .r

CI
(b)

,o CI

'.,o; G \Ar'
ll
CI CI

23. The maximum number of stereoisomers that could exist for the compound below ?

Br Br
(a) 6 O) e (c) 10 (d) 16
24. The following pair of compounds is best described as :

(a) identical (b) diastereomers

(c) enantiomers (d) none of the above
25. Determine the absolute configurations of the labeled carbons (a and b):
ab
SJ-dcr
\/-\
(a) o-R;b:R (b)o-R;b:S
(c) a:S;b:R (d)a:S;b:S
26. Which of the structures (a - d) will be produced if a "ring flip" occurs in the following
compound in chair form ?

27. Which of the following compounds is most stable ?

(a) 4Y (b) L
28. Which is the most stable chair form of this compound ?
 i

IffiII{ERIS*I

29. Which pairs of the salts would have identical solubilities in methanol ?
Ph Ph NHP
tl
(l) ,t*.r, cHr-fco; ,*in
H
(u) .r,*coo-
NH; H cHs Ph
Ph Ph r.rHP
l"l Ph

oru rvH$fcH, ,f.", lrynrrfH cHrfH

H cot cHg coo-
(a) I&ru (b) r&m (c) I&II (d) rr&ry
30. The following compounds differ in respect of :

(a) their chemical and physical properties

(b) nothing
(c) the direction in which they rotate plane of polarized light
(d) their interactions with molecules
31. Indicate whether each of the following pairs are identical, or ?
F

Br
H
qH
(r)
H
H
I ,r.icH2Br
cHs F
Gr)
,cH2cH3
'%.,
cHg cir2di{3
CH" cHs
r-r
l" Dr- er _J_H
-I- I I
(III) cH3l-H H--cH3
I
Br Br
Iil m
(a) enantiomers diastereomers enantiomers
(b) identical enantiomers enantiomers
(c) enantiomers diastereomers identical
(d) enantiomers identical identical
32. Which of the following is achiral ?

(a) (b)v
 ffi:'Stf#ffi.#

(c) (d) a molecule of 3-methylheptane

33. Which of the following compounds are meso forms?

CH"

+ &
H OHH _L_ C]

H OH Cl H
CH:
cH2cH3 cHg
1 ,
(a) 1 only (b) 3 only
(c) I and 2 (d) 2 and 3
34. The separation of a racemic mixture into pure enantiomers is terrned as :

(a) Racemization (b) Isomerization (c) Resolution (d) Equilibration

35. Rank of the following groups in order of R, S precedence (IV is highest) :

- CH(CH3)2 - CHTCHTBT - CHrBr - C(CH3)3

r234
IIIIIIryIIIIilIV
(a)s 2 4 1 (b)1 4 2 3
(c)3 4 t 2 (d)s 4 2 1

36. Which of the following is a meso compound ?

e)H 9)
h:rt.., j-H;,
FHs cH2cH3
Hgc
(a) (,,rH (b) r.r

H3c2-
El H
(d)'.iFt:'#, (.)H'cHcH2cr
V-7. Among the following structures, select E isomers (arrows indicate the bonds to be
considered) ?

,,rW
\cH,
- -"4 c" r::j&.';,:r'l^'
H,c.o-o,$-"
Hrc-o
\ YS .',
Jn,
(1) (2) (3) (4)
(a)land2 (b)1and3 (c)1and4 (d)2and3
38. Which of the following compounds has a zero dipole moment ?

(u)''\ol'*,6tr]: (c).,4,,0,.,d'
39. On Piutc. where everything is frozen., astronauts discovered trro forms of butane gauche and
anti. Assumlng rhat there are no rotations around single bonds, which statement about the
two forms is correct ?
(a) Thev are enanriomers
(b) They are diastereoisomers
(c) They are meso compounds
(d) The gauche form has rwo stereogenic centers, and the anti has only one
40. Which of the following will show optical activity ?
COOH cH2cH3 cH2cH3

,,,Jv:',(c, nfo'
H-4-oH (D) Ho-fu
Ho CH2CH,
--}-I
COOH cH2cH3 H
(E) 50/50 rnixture of C and D
(a) A, D and E (b) AandEonly (c) B, C and D (d) All except C
41. Among the structure shown below, which has lowest potential energy ?

42. Which of the following molecules islare chiral ?

H COOH

I (II) (IID Ho H

COOH
(a) I (b) rr (C) III (d) r, II
49. A compound was synthesrzcd by a student, but its strllcture was not identified. However, his
wonderfully helpful instmctor told him that it was a meso compound with 5 carbons and 2
stereogenic centers. Which of the following strucrures should the student consider as
possibilities for his compound ?
OH CO,H Br

(D Br (rr)Ho2c\.L;" (m)
T Br
I

(IV) qy1Br$r
(a) I, II, IV (b) II, IV (c) I, III, V (d) u, v, v
44. How many isomers are possible for the following molecule ?

,;rGcHCH: cHCooH

(a) 1 (b) 2 (c) 3 (d) 4

45. Which of the following molecules are chiral ?

0)Lb- (u)
cHg

H
H
(a) I, II, m and IV (b) II, III and IV (c) II and IV (d) I and II
46. Which equilibrium is not rapid at room temperature ?

(").,t4 Hb)^R,
Cl Me Cl Me
A
CI
Me

Br

(c)
Hsc

47. Which is the lowest energy conformation of butane ?

cHr

(a) (b)
{I
,.r";$;
H3 HH cHs H

48. Which of the structures given below are chirai ?

CH"OH cH2oH
',
CHrOH
-J-,
I,
|
HO HO
a,^;
-J-,
crfu
+. +,
HO
ctt) (IID HO (rV)
HO HO
cH2oH CHO cH2oH
Fischer proJectlons

0r)
,ra$'.
(a) I, II, III (b) II, III, V (c) II, III (d) I, II
 reaction with

ozN:,Arco2H
(b)

c02H Ho2c\rl*o,

(c)ffi
HO2C NOz
(d)

50.

CHO
(Fischer projections)

(a) enantiomers (b) diastereomers (c) identical (d) structural isomers

51. what are the correct designations for the structure below ?

,r^n-/'
LJ toru
(a) E, E (b) Z, E
(c) E, Z (d) wo geometrical isomers are possible
52. Which of the following molecules are chiral ?

OH OH CH"
l"
(M[>
:-

(r)* (il) I .-_. (III) HoWTVH

-re
i I go€(H
OH OH
cHs

(a) I and III (b) I and V (c) II and III (d) II, III, IV
53. Which one of the following isomeric structures has the lowest energy ?

,re( ,rrU.,
 (a) molecular comPosition (b) boiling point
(c) melting point (d) IUPAC name
55. Among the following, the most stable isomer is :
OH
^=-focH3 @
(a) La-J
s{ MoMe
(c)
OMe (d)M
oH ?M"

MOH

>-)
(b) t-Bu.-l+.-J1l
*.

(c) t-Bu
(d) t-Bu

57. which of the following molecules have non-zero dipole moments

?

(I) gauche conformation of 1, 2-dibromoethane

(II) anti conformation of 1, 2-dibromoethane
(III) rrans-1, 4-dibromocyclohexane (M cis-l, 4-dibromocyclohexane
(V) tetrabromomethane (VI) 1' 1-dibromocyclohexane

(a) I and II (b) I and IV

(c) II and V (d) I, IV and VI
58. What is the maximum number of stereoisomers possible for discodermolide ?

(a) 21a o) 21s (c) 215 (d) 217

59. An aqueous solution containing compounds A and B shows optical activity. A and B are
stereoisomers. Which of the following possibilities cannot be correct ?

(a) A has t'wo chiral centers, but B does not have any because it has a symmetry plane
(b) a and B are enantiomers
(c) A and B are diastereomers
(d) A and B are not present in equal amounts
60. Which of the following structllres represents the lowest-energy form of (1S, 25,
4R)-trimethyl -cyclohexane ?

@ry> I

b)x/
roM G)M
51. Which one of the following is a diastereomer of (R)-4-bromo-cis-2-hexene ?

(a) (S)-4-bromo-crs-2-hexene
(b) (S) -5-bromo-rrans-2-hexene
(c) (R)-4-bromo-ffans-2-hexene
(d) (R) -5-bromo-fraru-2-hexene
62. The structural formula of cocaine is shown below. How many stereogenic carbon atoms are
there in this molecule ?

(a) 1 (b) 2 (c) 3 (d) 4

 the stereochemical relationships of
compound I, II and III shown below ?

CHO CHO CHO

HH
I
I
H H H H

(I) HgC H (II)

H CH" (I[)
" H
I cHg
H
H
CHO
cHa
H

(a) All compounds are chiral

Hgc
H
+
CHO
HH
HH + CHO
cHs
H

(b) None of the compounds is chiral

(c) I and II are meso compounds
(d) I and II are diastereomers, and III is a meso compound
(e) I and II are chiral
64. What is the absolute configuration of the following molecules ? (NS : the molecule has no
center) Note : For the purpose of this question only, the order of stereocenters is not
specified ; i.e., R, S : S, R.

"'>d
CI

(r) (D

H2C:Na CI
-.CH-NH I
F7\e.
rrrr) ov,
t ) (M nr./r
^?o I
C1

IilMTV IU ru IV
(a)R R,S R NS O) N R,R S R,R
(c)R R,S NS NS (d) R R R,S R,S
65. The number of all the possible stereoisomers formed by the given compound is :

(a) 2
(c) 32
, ,,,,.. ",,,;i,..,i ,,:, ,r. *;i ,r;-,rriniiu;l'::ffif;1iiiiifiIi4ffij+ii{Jti*l;'.iii* ,;iiif,1i':.,111

66. The relationship among the following pairs of isomers is:

Otrl
(D
d"e (II)

BrBrBrH CHO CHO

><><
HHHBT
,,-|-on ro-]-*,
tt
cH2oH cH2oH
(III) (rv)

(a) I -A, II-8, III- B, IV -D (b) I-&II-A,III-B,[V -D

(c) I - B, II-A, III-B, IV -D (d) I - B, II - B, III -& IV - B
67. The stmctural formula of sativene is shown below. How many stereogenic centers are there
in this molecule ?

(a) 2
(c) 4
6E. Which of the following is the least stable conformer of cyclohexane ?

(b)U (Boat)

(c) D4 (TWist boat)

(d)d (Half-chair)

69. The S- enantiomer of ibuprofen is responsible for its pain-relieving properties. Which one of
the following stnrctures shown below is (S)-ibuprofen ?

o
I
c-oH FI

/
C,, ?'o.n,ao'
o) f*ca
f""an, Hsc \
H

70.
,.,fu$1 ,, ,.,fu,r|
Whidl of the following depict the same ?

cH2cH3 9Hs cH2cH3

=
Br >d'<Cl cH3cHz
= HrC >Q<Br
; -g<cl ?
cHs d' C1
I 2 3

(a) 1 and 2 (b) 1and3

(c) 2 and 3 (d) 1, 2, and 3
7,-. A naturally occurring substance has the constitution shown below. How many mdy have
this constitution ?

HO cH2oH

HO H: CHCH: CHCH2CHzCHg
(a) 2 G) e (c) 16 (d) 64
72. The absolute configurations of the two centers in the following molecule are :
1
COOH
H 12 st
I

H l3-cN
I
OH
(a) 2(R), 3(S) o) 2(R), 3(R) (c) 2(S), 3(S) (d) 2(s), 3(R)
79. The total number of stereoisomer possible for Z,3dichloro butane :
(a) 2 (b) 3
(c) 4 (d) s
74. Which of the following structure is not meso-2,3-butanediol ?
CH" OH CHO H
utoH l"
H-f-cH3I
Ho#n oH-f cH,
(a) u--l-cH, (b) Hfcu, (c) u-fcrr, (d) H-fHo
OH OH A, cHs
71. A solution of optically active l-phenylethanol racemizes in acidified aqueous medium. It is
due to :
(a) enolization (b) carbonium ion formation
(c) carbanion formation (d) reversible oxidation-reduction
76. The most stable conformation of ethylene glycol is :

(a) Anti O) Gauche (c) Partially eclipsed (d) Fully eclipsed

H
H oH Ho+cH3
H H-J
77. Br
l-t"'
Br
The molecules represented by the above tvvo structures are :
(a) identical (b) enantiomers
(c) diastereomers (d) epimers
78.. The correct order of priority of groups -SCH, (I), (II), CH (IID and
-NO2 -C:
GV), on the basis of CIP classification, is (increasing order) :
-CH2C6H'
(a) I, III, II, [V (b) IV, III, II, I
(c) II, [V, I, ilI (d) III, IV, II, I
 (c) 2S,3S (d) 2R, 3R
- enantiomer is represented by :
cooH

G) H-t--NHz
I

I
cHs

cooH
(d) H3GJ-NH2 I

I
H
meso compound ?

cH2
l' - cH3
H---F-oH
6; HJ_oH
cH2-cH3

(c)kN (d) All of these

OH OH
82. Predict stereochemistry of product when d and l-amine reacts with {-acid:
(a) Diastereomers (b) Meso
(c) Racemic (d) Pure Enantiomer

(a) + (b) s
(c) 6 (d) More than 6
84. Which dimethylcyclobutane is optically active ?
(a) trarc-"!.,2 (b) cu-l,2
(c) rrcns-l,3 (d) cu-1, 3
85. Which of the following is the enantiomer of the compound shown below ?
H

Me Br

MeH
Me
Br

+
Et
H
OH

H
| -''
Hter rra. Is.
*._ Br Me Br Me
(a) H#Br O) HfBr (c)
+ H
I
Br (d)H Br
no
-|-Et rvr. vr.
-l-oH Ho
Et
Me Et Me

How many different stereoisomers are possible for the following compound ?
H
I

CIHC:HC-C-CH:CHCI
I

CI
(a) 1 (b) 2 (c) 3 (d) 4
87. The following compounds are best described as :
(R)-PhCH(oH)CH3 and (S)-PhCH(OH)CH3
(a) enantiomers
(b) diastereomers
(c) not stereoisomers
(d) conformational isomers (differing by single bond rotation)
88. Rank the following substituent groups in order of decreasing prioriry according to the
Cahn-Ingold-Prelog system :
-CH(CH3 )2 -CH2Br -CHrCHrBr
(a)2>3>1 (b)t1 ,3>z ' (.)3>13>2 (d)2>1>3
gg. Compare the stabilities of the following two compounds :
A : crs- 1 -Ethyl-3-methylcyclohexane
B : frans-1-Ethyl-3-methylcyclohexane
(a) A is more stable (b) A and B are of equal stabiliry
(c) B is more stable (d) No comparison can be made
90. What, if anything, can be said about the magnitude of the equilibrium constant K for the
following equilibrium ?

cH(cH3)2 Hsc
H
-- cH(cHr2
(a)K-1 (b)r(<1
(c)K>1 (d) NIo estimate of K can be made
91. what is the relationship between the two su:r.rctures shown ?

(a) Constitutional isomers

(b) Stereoisomers
(c) Different drawing of the same conformation of the same compound
(d) Different conformation of the same compound
92. Which of the following statements is tme ?
(a) van der Waals' strain in cis-l, 2-dimethylcyclopropane is the principal reason for its
decreased stability relative to the trans isomer
(b) Cyclohexane glves off more heat per CH, group on being burned in air than any other
cycloalkane
(c) The principal source of strain in the boat conformation of ryclohexane is angle strain
(d) the principal source of strain in the gauche conformation of butane is torsional strain
98. ph _CH : NO2H_-ffi- (x) , Isomer (x) is
Fs (sesoorf
:

(a) Ph NO CH2OH o) Ph - CHz - NO,

(c) Ph - NH - CO2H (d) None
- -
94. which of the following will not show geomeffical isornerism ?
(a) CH. : CH CH2 CH3 (b) CHs :
-f - - 1" -CH
CH
- CHz
- CHs
cHs cHa
(c) CH, CH : CH CHs (d) CH3 CHz CH : CH CHz CH,
- - - - - -
95. The two compounds shown below are :

Y\'
Y and

96.
(a) diastereomers ful
"#35*urc
The molecular formula of diphenylmethane,
,.r#: (d) regiomers

'isc13H12i
@*r@
How many structural isomers are possible when one of the hydrogen is replaced by a
chlorine atom ?
(a) 6 (b) 4 (c) 8 (d) 7
97. Correct configuration of the following molecule is :
QHe
,-I-o,
I
cH3-T-oH
H
(a) 2S,3S o) 25, 3R (c) 2R,3S (d) 2& 3R
98. Maximum enol content is in :

o oo o oo

99.
(a) /r (b) /\A
Which of the following will have one of the stereoisomer meso
r.lA,
?
cal ,nAAnr,

(a) 2-chlorobutane (b) 2, 3-dichlorobutane

(c) 2,3-dichloropentane (d) 2-hydro)qpropanoic acid

$&r
1OO. The correct decreasing order in the enol content of following molecules is :

(r) (D (rrr)
(a) I>II>III o)II>I>rII (c) III > II > I (d) II > III > I
1O1. Total number of stereoisomers of the compound 1-bromo-3-chlorocyclobutane is:
(a) o (b) 1 (c) 2 (d) g

lO2. Total number of stereoisomers of the l,3-dichlorocydohexane is:

(a) 0 (b) r (c) 3 (d) +
1O3. Total number of stereoisomers of the compound 1, +dichlorocyclohexane is :

(a) 0 (b) 1 (c) 2 (d) 4

1O4. Total number of stereoisomers of the compound 2-4-dichloroheptane is:
(a) 0 (b) z (c) 3 (d) 4
1O5. In which of the following keto form is more dominating than enol form:

,r+
o

&) (c) (d) all of these

o
106. Among the following compounds, which will give maximum enol content in solution :
o o o o
il il il il
(a) C uHu
-o
C- CHz
-
C- C 6Hs G) cu,
- oc- cHz - c- cH3

lt il
(c) CH,
-C-CHz -CH2 -CH3
(d) cH3
- c- cHz
-cooc2Hs
IO7. Which of the following has unstable enol form ?
o

(a) T{: "r"v @)ff (d)

O
1O8. Calculate enantiomeric excees of mixture containing 69 of (+) 2-butanol and 49 of
(-) -2-butanol.
 (a) LOo/o (b) 2oo/o (c) 4ooto (d) 330/o
1o9. which of the following pair represent pair of diastereomers ?
(a) Meso tartaric acid and (D tartaric acid

CO,H CO"H

(b)H +
ro+,
CO' cot
cH?-cH3 o O CH2-CH3

t l" l \lC-O-H
(c) -T-- andll
cHs H-f-oH H#OH CHs
I
CHs cHs
(d) All of these
110. The stereochemistry of this molecule is :

QHs H
s*|cr
b-\/
(a) 1R, 3R (b) 1R,35 (c) 15, 35 (d) 15, 3R
1l'1. Pure (S)-2-butanol has a specific rotation of + L3.52 degrees. A sample of 2-butanol
prepared in the lab and purified by distillation has a calculited specific rbtation of +6.76
degrees. What can you conclude about the composition ?
(a) 500/o (S), 50% impuriry (b) 50% (S), 500/o (R)
(c) 50% (S), 500/o racemic (d) some other mixture
112. Determine the absolute configurations of the chiral centres in the following compound.

(a) a=R; b=S (b) a=R; b=R

(c) a=S; b=S (d) a:S; b:R
L13. Total number of stereoisomers possible for following compound is :

CH: CH-CH2CH3

H:CHz
(a) B (b) 16 (c) 32 (d) 64
114. Which is the correct stmcture of D-glyceraldehyde ?

CHO H CH"OH
(a) H*o, o) Hof."o (c) Ho
{H
(d) Alt of these
cH2oH
'o cH2oH cHo
il
115. HO
-CH,-CH"- C- H
(3)' (2)' (1)
Which conformer of above compound is most stable
(consider conformer across (Cz
(a) Staggered -Ca)
(b) Gauche (c) Fully eclipsed (d) Partially eclipsed
cH2 - oH cHo
HtoH Ho H HJ-OH I

116' Ho
-4- H I
Ho H H
-f- OH
I
CH29H

CHO CHO
(a) (b) (c)
(D) & (L) Configuration of above carbohydrate is :

(a) L, L, D (b) L, D, L (c) L, L, L (d) L, D, D

117. How many isomers have the name bromomethylcydopentane ? (ignoring chirality)
(a) 4 (b) s (c) 6 (d) 7
118. Which of the following compound can show geomerical isomerism ?

119. Which of the following structure represent meso-compound ?

(a)

(c)
12O. H

How many representations of lactic acid are possible in Fischer projection (d & I) ?
(a) 8 O) rz
(c) 24 (d) 36
tzl. Total number of stereoisomer formed by the given compound is :

(a) 2 (b) s
(c) 4 (d) 8
1,22. The number of stereoisomers formed by the given compound is :

t"Y*-ro I

oA*A.,,
I
H
(a) 2 (b) s
(c) 4 (d) s
123. Which of the following compound does not undergo base - catalyzed exchange in DrO even
though it has an o-hydrogen?

(c) (d) both O) & (c)

*
o

p-o/oH- product
,
long time

Identify the product formed in the above reaction:

 (d) None of these

L25. In 3-methyl-2-cyclohexenone which hydrogen cannot undergo deuterium exchange when it

reacts witir CurOo,zCH3OD ?
o

(a) Hr, Ho
(c) Hs, Hz
ry" o
(b) H4
(d) H5, H3

1,26.

The tautomer of II is :
0 (u)

(a) I (b) III

(c) both I and III (d) none of these

o
Hc

127.

In the enolization of the given molecule, the H-atom involved is :

(a) cr-H (b) B-H
(c) y-H (d) cannot be enolized
 o
(r)
c:G
(ID (IID

Among the given stmcture which can exhibit tauromerism ?

(a) I orb. (b) II only (c) Itr onlr' (d) none of these
o o

0) (u) "i II'

Identify the which can exhibit tautomerism ?

(a) I only (b) II only (c) III onll' (d) all of these

13O. CHs-CH : O# CH, = CH-OH

(D (D
Between the trnro tautomers which is more stable ?
(a) I (b) rr (c) I=il .d none of these
OH OH

131.5
(D
<s5 OII)

ff
Correct stability order of the given tautomers is :
(a) I>II>III (b)llt>II>l (c) II>I>III (d)II>m>l
OH
132. --
-.r..\

(IID
Correct stability order of the given tautomers is :
(a) I>II>III (b)rrr>II>I (c) II>I>III (d) II>lll>l
oL---ro o\-
133. +te\ xo/o I

R-=q,,
QH

[-1==-=l-ll z o/o

The corre., oro.hr"rro, *kz is :

::':i":r:::
,,tt t,

xsffiEilfi
:.

(a)x>y>z (b) z >y>x (c)y>x>z (d)x> z>y

.o
J OH

134. <.): // \
\o/
-/ xo/o :

n
qo--' -\n q ,roro(x,y,z
represent enol content)

The correct order of x, y, z is :

(a).r>\'>z (b)z>y>x (c)y>x>z (d)x>z>y

i.a'r , (U) ,, (c) III (d) none of these

136.

Product
The product of this reaction should be :

9Hs

(d) All of these

137.
??q)ooo (r)
(r) (m)
Among the given compounds, the correct order of enol content is

d
:
(b) rrr >II>I (c)II>I>III (d)II>III>I

138. 6
Y Y o o
.o

(r) (r)(rr)
Among the given compounds, the correct order of enol content is :
(a) I > II > III (b) ltt >II>I (c) II>I>III (d) tt>III>I
 Ofi C Chernistry far IIT'IfrE

L3g.

(II) (m)
Among the given compounds, the correct order of enol content is :

(a) I>II>III (b)IIr>rr>I (c) III>I>II (d)II>I>tII

140.

How many geometrical isomers are possible for the above compound ?
(a) 3 (b) + (c) 6 (d) B

1.41. Which of the following compound lvill not shorv geometrical isomerism across the ;r-bond ?
lcl

(b)

=
Br Br
CI Cl F F'

(c)

Br Br

1.42. \:&"
t1 !2---""'111
Choose the correct relation between l, and l, ?

(a) l, = 7, (b) 11 > 12 (c) \..12 (d) l, = 21,

l-- TT
"-

t4B. \a :'a : c: ca
HAIZSH
Choose the correct relation berween l, and I, ?

(a) l, = 1, (b) 11 > 12 (c) l, .1, (d) l, = 21,

cHs
144.
cHs
How many geometrical isomers are possible for the above compound ?
(a) 0 (b) 2 (c) 3 (d) 4
rsollfisfix$M
cHs
145.
czHs
How manv geometrical isomers are possible for the above compound ?
(a) 0 (b) 2 (c) 3 (d) +

146.
# cHs

How many geometrical isomers are possible for the above compound ?
(a) o (b) 2 (c) 3 (d) +

147.

Br
Hort, man\- geometrical isomers are possible for the above compound ?
(a) 0 (bl z (c) 3 (d)
CH:

148. cHs
cHs
I-low many geometrical isomers are possible for the above compound ?
(a) o {b) 2 (c) 3 (d) 4
t"t' cI{3

149.

How many geornetrical isomers are possible for the above compound ?
(a) o (b) 2 (c) 3 (d) 4
H

cHs

I and II are geometrical isomers of each other because

(a) \ =1, (b) 11 > 12
(c) l, , l, (d) lr andl2 cannot be compared.
151. CH2 : CH -CH = CH -ClI = CHz
How many geometrical isomers are possible for this compound ?
(a) 2 (b) 3 (c) 4 (d) B
153. :CH_CH,

GN-oH
R

*o
I

OH
(a) chiral (b) C a axis of symmetry
(c) Optically active (d) All of these
CI CI

155.

Br(A) Br

Relationship berween above pair (A) & (B) is :

(a) Enantiomer (b) Diastereomers (c) Identical (d) Structural isomer

fr tu
156.

NHz

' NHz
(A) (B) (c) (D)
From the above compound (A), (B), (C) & (D) chiral compound is :
(a) A G)a (c) c (d) D
 bg4

157. Which of the following compound is achiral ?

o)

co2H

9Hz

1s8.
cH2-o-cH2-cH3
:
CH3-(CHz)+r
,.r? ,ra("2)5-cH3
\(cHz)s-cHs
t"TcH2-cH2-o-cH2-cH3
cH3-(cH r){
(A) !*,
R and S configuration of compound (A)& (B) will be :
(a) R, R (b) R, S
(c) s, R (d) s, s
159. Which of following compound has center of symmerry?

Br
o
il
Hrr"._/ NH - C

(a) T"@T", G) cHn.-*rAn

\......CHg

L,-5y-l* il
o

Br
-,
cJ{s

(c) (d) All of these

CI
L6O. Which mixture of structure in each beaker would rotate plane polarized light ?

cHs
(a) (b)

N4
cH,-f!{ -oH
CH

CH"
H--ljon
HtOH
I

(c) CH" (d) All of these

" CH"
t'
HtOH
HtH
CH

161. Which of following compound will rotate the pla ne polarized light at room temperature?

(a)re,',ffi(c)
162. \tVhich of the following having plane of symmetry ?

(b)

(c) (d) All of these

f.#$ ffiI$.Jyt
1"63. Which of following compound is achiral ?

(a)

(c) H (d) All of these

164. Which of the follolving compound has plane of symmetry ?

R=-CH-CI , S = -CH-Cl
I I

CH, Br

(a) n (b) s (c) (d) None of these

EJ<
1-65. Which of following is E isomer ?

(a) (b)
,<3
\)

,.rt}.:d
166. Among the given pairs, in which pair second compound has less enol content than first
compound?
o o
Oo

!o)
AA-
oo *,4'A
(c) A,A (d) none of these
167. Which of the
NHz

(a)
o S *)ro-* **-ot*
,., \A, -.-,{, = Resonance (d)
Hto*
ll
6 :-- Ihutomers
o H.
168. Ph-cH-[-, 'o'
H'o
, (B) ; (A) and (B) are isomer and isomerization effectively
I
OH
(A)
carried out by trace of base (B). Identify (B).
o o
il lt
(a) Ph-CHz-C-O-H o) Ph-c-o-cH3
o o
il ll
(c) Ph-C-CH2 (d) H-c-cH,
-OH -o-Ph
169. : CH : of geometrical isomer is
CHs
(a) 2
- CH CH - CH
- CHr; total number
(b) 3
:

(c) 4 (d) 6
t7O, Identify most stable enol form of terric acid:

o
H

(a) o o)o

(c) o (d)o
l7l. Which structure is most stable ?

OOOHOOHO OH OH

172.
(,),4.,4. ,orAA. (.),{.A. @AA
Identify conformer of 2-methly pentane :

(a) tb)

cH2cH3

(c,:H: (d,
H

173. The lowest energy conformer of

(a)
H R H
(b)
.F"
(c)
R (d)
.R.,
1,74.
J
Ctr.ttt'"

How many atoms will be bisect during plane of symmetry ?

(a) 2 (b) +
(c) 6 (d) 8
 $ftcffi fo*,i***rrE
The number of all types of isomers of chlorobutane is:
(a)2 G)+
(c) 6 (d) s
lT6. Which of the following pairs of compounds are not positional isomers ?

nogt"'
(a) and
,(/o"
CHs

(b)
.r9o, rart"
and
Yon

(c)
€),t",on ".0 lilot''
(d) All of these

lZ7. Which of the following pairs of compounds are functional isomers ?

As/ o o
(a) ry
and
oH
(b) ) ana
)) ,
o

(c) A.,/oH urd, /\/o (d) Ao' ,"d /Y

o
1-78," The isomeric alcohol which has a chiral carbon atom is:
(a) n-buryl alcohol (b) rso-butyl alcohol (c) sec-buryl alcohol (d) tert-buryl alcohol
l7g. The pair of enantiomers among the following compound is:
CH, CH. CH, H
l'l"l"l^-,
ph-lH H#sr Ph*Br BrfcH3
l^'l-ll
BrPhHPh
I II III IV
(a) I and IV O) tt and IV (c) II and III (d) I and II
180. Which of the follorving is chiral?
(a) Ceil phone (b) Spiral staircase (c) Scissor (d) Nl of these
1g1. In which of the follorving compound, possess plane of symmetry as well as centre of
symmetry?
CH" cHs
"a,
\ ,$cl
\--'.."'*t'
(a) I--l
ll
(b) Ll (c) qr,to'.rp
\tt.." \
% C1
 (a) ,rrd- ,.r..
projection
183. For the following Newman

" ti'-, "

,,4\, H

cr (c)
H

(a) (b) ;tX ;X" (d)

^Au H nX,t ",;/"

is correct roi ,rr. given compound?
184. *nr.n or *,Xrotlowing

(a) It possess centre of sYmmetry

iui r, pott"tt co axisofofsYmmetry
sYmmetry
i.j It possess Plane
a coaxial plane of svmmetry?
185. $L:;yrn"fli,t"*#'*olecules has axis of svmmetry and
rA
o

crl HAH olt'p-t' ,',?t{ (d)

(e) Atl of these

Number of diastereomer
of given comloun-d :
186.

"-#
*r#
C1

C1

n* CI
cHg
(c) 4 (d) 6
(a) 2 (b) 3
187. Which of the structures islare diastereomer of A ?
o

$ &
=

(1) ,rr"'xf
\,AO
(3)

o o

(s)

(a)
$
3
o
O) tand4 (c) 2 and 3 (d) s
188. Identify which of the structures below are meso structures ?
o

",J:\ (r) ""(oY ,rr"# ,-,Yh

o o o

t".."'&
(a) L and 3 (b) 1,3 and 5 (c) 1,3 and 4 (d) 2 and 5
o
il
189. How many enol form is possible for CHs
-CHz -C-CH2 -CHz -CHs
(including
stereoisomers) will be ?
(a) 2 (b) 3 (c) 4 (d) s
19O. Find the sum of all the stereocenters that are present in below compounds :

cHa CHs cHs

H cHs

(r) (III)
(a) 8 (b) e (c) 10 (d) 11
191. A pair of stereoisomers might be dassified in various ways. Which of the following statement
are true with respect to pairs of stereoisomers ?
(a) They might be configurational isomers (b) They might be diastereomers I

(c) They might be constitutional isomers (d) They might be tautomers

(e) They might be conformational isomers (0 They might be enantiomers
(g) They might be positional isomers
e
(a) a, b, c, g
(b) b, d, e, f, (c) a, b, f (d) a, b, c, f
192. Ignoring specific markings, which of the following objects are chiral ?
(I) a shoe (II) a book (III) a pencil
(M a pair of shoes (consider the pair as one object)
M a pair of scissors
(a) Ionly (b) I&V (c) I, IV, V (d) III, [V, V
193. Calculate the total number of stereoisomers when alkene having trans configuration

k\-l.-
a

(a) 2 (b) 3 (c) 4 (d) I

I os.

89.

t 69.

177.
185.
f$r0ffff&.{$Jfd $.I$

Match the Column (I) and (II).

CHs N-OH
-CH:CH-CH:

CFI3 --"CH :- CH *CH * CH : CH

CH CH3
- -
CH: CH-CII: CH-CH: CH -Ph
-CH:
2. Match the Column (I) and (II).
R

'---- I\\/'!
I
Keq

t-"+l l-->R

{a}

(bI
r
(c)
#fi#1.

3. Match the Column (I) and (II). (Matrix)

tr ;f;i*,ffi

4. Match the Column (I) and (II). (Matrix)

Compoun$

Geomemical isomerism

,ft]

Compound containing plane of symmetry

Compound containing center of qnnmetry

1r.6 ORS,ilVf C€ft erm{"*rryrforI,{ff*I.#

5. Nlatch the Colurnn (I) and (II).

fi[HffidfiIHil

ft;: andft:,

\ /c*,
i

and
O.-.,
t

^)<cl
I

Structural isomerism
s i

i
cHs
_l
Match the Column (I) and (II). (Matrix)

Cbmpound

cis-compound

rrons-compound

cHsHo

,,lrrrttCH3 Optically active

UtcH3
cHs
Idt) t*) I optically inactive
cHs
ISO][,IER.ISI}{ 1,S7

7. Match the Column (I) and (II). (Matrix)

,. ,,:. Pr€perty
H\c-(:
r/H
\ Chiral centers containing compound
ct/ ct

.'><"' Presence of stereocenter

Optically active compound

Compound containing plane of symmeury

8. Match the Column (I) and (II). (Matrix)

Molecule F, peffi
F\c-f,-:-c-_
(sl c/H
\F
H./

(h)
:>c-c-.<: Opticalty active

(c) .rtllF Optically inactive

t'
1,
1..
,,
i:
{:
N
F

i[i],,,(d)
':
Plane of symmetry
H
l:'
T.

I.
N

l. ,:,
ffi'*ffi iliiiil*i,riffi ffi ffi *ffi lr'r++ilt*lr$rl+
9. Match the Column (I) and (II). (Matrix)

,$.#

Me
V..sH

(,

Me
V.no'

G':" Chiral compound

ffiil Compound will show geometrical isomerism

ISO]WERI.-,$JW ,, .' ,, ..,.,.,,'
,.;, ,..,, 1r
1,fi9.

10. Match the Column (I) and (II).

Fully eclipsed

u CHs
Partially eclipsed
 ORGdtrfC Shenr**fl $lt ?;JEE
1L. Match the Column {'t} and (II}.

t{,e ann Proje*ion N ,, f,,'ffiq.,Coffipdr*nfr

cHs
{aI (FT 3-methyl pentane
H

cHa

H3
{b} tq) n-butane
H

{c} (r) Methyl-cyclopentane

:&: fn' H

Id] (s) 1,2,4 -*imethyl ryclohexane

cHs
i

cHs
ISOIWERISIW itfilliil:iri

L3" IMatah the Coiurnn (Ii and (II). (Matrix)

i, (a) (p) Rotates plane polarized light

:

{b} ,(uI Cannot rotate plane polarized light

.,,,,. :

Br

ta3
,trHb) ,r'"
(r) Plane of srimmetry
I

AsMe3

(d) (s) Centre of symmetry

13. Match the Column (I) and (II).

nnai**ffi
CH: CH-CH--CH3
-CH:
b'

H __C : C -- CH :=CH
-CH-CH__CH"
ilo
Br Br

lo
(") I Ph
- $-., : cH-- qH-cH:
 iiiia:ilii$, iffia ##ffi,t#i',t,itr;f-iHE

Stereoisomers :

i$#,,,il
(fiI

tq)

(r)

iffi [r]
ISOIfigRIStrffiffi.i titLit'ii,t, i
fi##
L5. Match the Column (I) and (II). (Matrix)

Meso Compound

o Me

\ C- C-Me
ll
Compound having even no. of
chiral centres

.-4

Optically active compound

COOH

--f-
I
H oH Compound having odd no. of
HtoH chiral centres.
COOH
trlw;
L6. Match the Column (I), (II) and (III). (Matrix)

ffi$XXifitxffi #***Gr
CH3
\C
Optically active
/ I
H H

r )FcH3
ft) (-F.r, Optically inactive

go
I

cH, N HCle'
(c) -* I
- Plane of symmetry
Et

f,
lr,,
(]
!*
:

:G Centre of
symmetry

--..I
cH3Yo)
(n) cHe (b) ($L
l \o&.r,
H'aC ,/H
cHsr tcHs
{G},
_ C: C ($J '6:C:C' .[$
H/- \H H/ \H

kI
2f
(='oi"' ffi
OH
=

From the above nds select :

i-*-*:r---
i (A) I *o of which are chiral and contai" qgd ru"gu
'
rwo of which are achiral and contains chiral centre :

rwo of which are chiral and does not contain chiral centre :

rwo of which are achiral and does not contain chiral centre :
 lAB

CI

CI CI =

CI CI

C1
(a)
C1

CI C1 =

CI C1

CI
(s)

Consider the given structures and answer A, B & C.

A. Which of the compound is optically active ?

(a) P (b) R (c) s (d)

B. Which of the isomer is most stable ?

(a) R (b) s (c) r (d)

19. Identify relationship between following pairs :

Q0zH
FH
(ilI (b)
ct?Br erOct
HH HF
co2H co2H

OH OH cHs \\CH"u
a-r^ r--ilr
(dl
fiGt
F \Y "-H
cHs

If they are enantiomer answer will be 1, if they are diastereomers answer will be 2, if they are
constitutional isomers answer will be 3 and if they are identical present 4 as the answer. Sum
ofanswerofeachparta + b + c * dis : . .
**$ ff ..C ffiffiffi
20. In each of the following three questions a hydrocarbon is named. For each select from among
the sixteen conformational structures (a through p) all structures that represent possible
conformers of that compound. Write letters (a through p), corresponding to your selections,
in each answer box.
A: 2-methylbutane
B; | 2.3-dimethvlpentane
Gt 1 -ethyl-L, 3-dimethyl cyclohexane

H SFl3 rbc H

.,tu,I-i,.t't
c zlt *.$'* rLC
qH3
c zlt

H \ -cH,

CTL *rru
CTL
.*,I\rczrL

C}L
.,.Kr*
n cH:

c zlt C FI?

rb.kf.u,, I.
\.-.--.,/tCFL
I

czrL

tr cHg l\---t

.,:#6L, .a;:-
\.,\czFL
ac':1,-1f,!czrt
I

c FI3
HH
1

I
I
H czHs
i

H
i tpt
i'
i
cHs
i
]
T$O,].t EftIS'W
21. Examine structures a through j, shown below, with respect to their symmetry or lack of it.
Assume that the five-membered rings and the ring in compound g are planar. The
wedge-hatched bonds in b, c, d & e designate specific configurations. Also, for the acyclic
compounds assume stable anti conformations. Answer each of the following questions by
writing letters (a through j), corresponding to your selections, in each answer box. If there is
no structure that fits the description enter an x in the answer box.

ta) (b) (c)

(d) (e)

(s) (*l c2H;clilctczFrs

c2HiCHCI2

crHrcHClcH3
0)

22. (i) l,2-dichlorocyclopropane w =

(ii) 1,3-dimethyl-eyclobutane
=x
(iii) 2-bromo-3-chlorobutane = y
(iv)L,3-dimethyl cyclohexane - a
Calculate total number of stereoisomer of the above compounds.
Sumofw+x+y+z-......
:$s#J ,,,, .,',-..:,...'..,.. . .: "

23. Examine the following tbrmulas arrcl select those pairs that satisfrr the following conditions :

Be sure to write two letters (and only rwo) in each answer bc,x, unless you select f. tn the
second and third parts more than one answer: is possible.

cHs

No formulas rneet the

,,.,,L+czHs
rr
designated condition
cHg

Which are identical in all

l,Vhich are conformational isomers?
TvVhich are constitutional isomers?

24. Examine the following formulas and select those pairs that satisfu the following conditions :

Be sure to write two letters (and only two) in each answer box. In the second and fourth parts
more than one answer is possible.
 Consider the followins statements r

W and Y are di
Z is the oroiection of X
W. X. Y and Z are optically active
Y and Z are isomer
26. Examine the followin srmcrural formulas and select those that are chiral.

er:x AA.O,'
NH,
")e(
co2H

AA r1-
I

--T-:
OH I
CHz - cHz - co2H

cHs\
ff**, cHs
C:C:C /cHs
H./ \H

-T-
I

---r--
I
cH3
Write your choice here
 using various kind of
through h) indicating

' ,,' .Q,'

i' ll'
:

^H '' '."1

][fi] cH3cH2
- Cf'oI] &.} , ,,C+.iH *..-€:;;LHre
cHs
ffiH czHs

, ,' icH*, cHs OH

CH2 ..+ Br
$;,itlt H H
tfil ,'}.h,
trJ

o ! iitiii i!:iillri i
cHe
H
OH
H

(8l
cHz: r(""",
iii'iii.i
cHe

28. The structural formula of ten compounds, (I) through (X) are drawn below, you may select
any one of these structure.
.Answer the following question about that compound.
 HO
il.ii

:ho m
cHs

ffi r ''..:o VI

OH
CH,,,,A
ilfiilill

OH
IX
,*H 6H
D
r..ln3l ;
df f
-

Y\t\
t/
a*rt OH

A. How many chirai centre are present in this compound ?

(a) o (b) 1 (c) 2 (d) 3
(e) 4 (0s
B. Is this compound chiral or achiral ?

(a) Chiral (b) Achiral

C. What symmetry element are present in this compound ?
(a) None (b) P1ane of symmetry (c) Center of symmetry
29. The structure of one of the enantiomers of the amino ;rcici cvsteine is shown below.

Classify this structure as :

(a)R or S (b)DorL
 ':,,r".,,1i,,,..1.
,.,:,,:' ,,
' .'r, .., .. ,,1:i .,..t
,,,'
... l.': ,

the following double (N) in the compounds given below

rl
A.

B. (a) Bongkrekic acid is a toxic compound produced by Pseudomonas cocovenenans, and

isolated from a mold that rows on bongkrek, a fermented Indonesian coconut dish. (a) Label
each double bond as E, Z or neither (N).

(b) How many total stereoisomers (including all Vpes) are possible for bongkrekic acid ?

(c) How many sites of unsaturation are present in bongkrekic acid ?

 jiri :.', alr ..l-:'ji:.')::ia',':::.:a:.:
: ..:. :j1.- ..::. , ,.,,:
r rr :r:ji. :.i it,,: ri;.,1 :t,fi ..': ::_::,:ar, .

Designate the following as E, Z or none (N) configuration

provided below.

o
a\ NH2
l-o OTr'f'
E 3

32. The follolving compounds may exist as rwo or more stereoisomers. These may be classified
as enantiomer pairs or meso compounds.

coH
coHr,
(a) (b) ,H.
fozt{
coHs HO.C' 'CUH'

ff
truxillic acid
truxinic acid
c\
/cl
co2H (d)

(e) C(CH3CHCI)4 (0
]l+co2H
cl\.4.
cl\,4.
G) I tscHCo2H
(h) I >c = cHCozH
ctN ctN
Answer the following question about the above structure.
(A) Total number of stereoisomers :
(B) Number of enantiomeric pairs :
(C) Number of meso compounds :
 iii,lrjili..iiiiirxiliirjl.il,r| lillrlilllffiif'rilti'x.l'qi$iiiilii'sii;iis.iitxiXi

Identify axis of symmetry in the 1

(2)

*'-T&o)-r
(3)
)r,,.$6 o o.A*,rNI"
[Y' e "Y\ (4)
''ft.,
Cl=ftrr
4Y CI

'\.-\, Mezc,J-A\r",
(s)
\.''\.{-cl
il Br
(6}
ki- CMe3

s-O O

\.A.-v"
(s) A*A
{
o
il

(e) ,rr*
34.

I.l,(CHg),
i''=
\z
(1) NCH3

morphine

vo,
(3)ffiw(4,
soN amoxicitrlin

*otro
F

o v,o
.''{w fO1.o-OSO2NH2

topomax
(6) t*strY (
,*-\A/ zocor
 H
l,$,i

co2H

Bi
,J
ff.i

on Ho{-H
$; oH Ho--l-H
cHg

5.

fjl,,

ffi
 9.

1O.

,i:i:i.iii

Strtrctural formula *t *T"T:rd (A) is following:

, sorc-&co2H
LJ
The correct statement(s) about the compound (A) is/are:
(a) The total nurnber of stereoisomers possible for (A) is 3
(b) The total number of mesoisomer possibtre for (A) is 1
(c) The total number of pair of enantiomer possible for (A) is 1
(d) AIl of these
B. Number of plane of symmetry in cis-form of compound (A) is:
(a) 0 (b) 1 (c) 2 (d) 3
37. Match the column. (Matrix)

No. of -r.nrr'rllli"o*"i ' ,'i

"t
{al C+Ftro (p) 2

&J csFte tfiI 3

tGli cort+ (t'I 5

t6il czrlr6 (*I 9

f;#ff,i.l:.;,.li:',,i 1,.,::,
"1

38. Match

ilg. Draw a most stable conformation (N - C) bond in the following compound.

H
\ii-[:.at
t{ -H
--,.,--n+l*i_.e--JBnry

40. Find total number of stereoisomers for each compound given below :

o
il
(1) Ph - S -CH = CH -CHz -CH : C =c:cH-cH=cH-cHg

ctls

,r,
cH4ll-
(3)
C1

mr
(4) Ph-CH-CH-NH-CHg
oH
tl cHg

o o
lt il
(6) H-O-C-qH-qH-C-H
tl
OH OH
 ,r, ]GcH-cH=cH-cH3

(10) CHs - CH : CH - CH -CH3 (t,)<l-cH-cH3

Br

41. Find the total number of stereoisomer for each compound :

$) a, A<b ---r ? (2)a,Ab-b

,r,,/\o-.

42. Match the column :

iiffi ,,Xsomeric Relationch&r

I

Chain

r\
iiil
cH3 -cH2 -cHz -C -oH, cH3 -cH- cHs Positional
I
 on#. ,Gherni$ffi,ffi,rrtr

43. Find sum of stereoisomer of following compound.

Number of stereoisomers

(a) (a)

(b) (b)
HO

F?Ei
(c) FIOCH,-CH-CH-CH-CH-CH,a
r-CH*CH-cH*cH-"c H2-oH
' (c)
'L I I I ---+

(d) (d)
ff 14r.

44.

Prostaglandin E1

Prostaglandin E1 1 is a compound produced by the body to reguiate a variery of processes

including blood clotting, fever, pain and inflammation.
Which of the following functional groups is not contained in 1 ?
(a) A ketone (b) An alcohol (c) A carboxylic acid (d) An aikene
(e) A nitrile
How many asyrnmetric (stereogenic) centres are present in compound 7?
(a) 3 (b) + (c) s (d) 6
C. How many up2 hybridised carbon atoms are present in compound 1 ?
(a) 1 (b) 2 (c) 3 (d) +
D. What is the geometric configuration about the double bond in compound 1?
(a) E (b) z

45.
H

Ethynylestradiol (1)

The synthetic steroid ethynylestradiol (1) is a compound used in the birth control pill.
How many rp3 hybridised carbon atoms are present in compound (1)?
(a) B (b) e (c) 10 (d) t1 (e) 72
How many rp2 hybridised carbon atoms are present in compound (1) ?

(a) 4 (b) s (c) 6 (d) 7 (e) B

C. How many sp hybridised carbon atoms are present in compound (1) ?
(a) 2 (b) 4 (c) 6 (d) B (e) 10
D. Which of the following functional group is contained in compound (1) ?
(a) A ketone (b) An alcohol (c) A carboxylic acid (d) An ester
E. How many asymmetric (stereogenic) centres are present in compound (1) ?
(a) 2 (b) 3 (c) 4 (d) s
1,.1.:.:.r1. i.l;r ,.,:.1::l.rl , I .l ,,,:,.1,f,i]lff1f;,:j,

Match the column.

(r)
1. Number of chiral isomers are:
. C1'' ''
-L -Cl
ttrt\ \
H.*

(.)fu
C1 CI C1
I
I
(b) (d)
(a)
,z\'cl nz$tr t.7\,
\./\t
.^'--/\\.1
\/
HIH
H
CH"

t"n$,
Hrj\,H H 4[\ ,^t\ l"
tn'LC&',l
vr
(s)
\-|/
Consider onlY a
(h)
<-l-/ CHs
H ,conformation with Me
fl",ii::riltlilff
CH"
(i)FI...
><
W r11
7H
U) (k) \ \Cl

2.

Number of stereoisomer are

(ii)
3. (i)
O*-,,1:],,
CH: ,1,,

(c)
Sum of number of stereoisomer (C) Degfee of unsaturations in (D).
-r-''---'

4. How many 5 membered parent chain alkane are possible for C7 H16?
I

b. Theoretical possible geometrical isomer of t

l--.4 I
 ffi
6. Total number of possible structural isomers of C 5 H11Br.
7. Total number of plane of symmetry present in given compound is

8. Total number of
.lm:l
isomers for C 4H6Br2 containing cyclobutane ring are ( including
stereoisomer) ?
9. Total number of structural isomers of CqHre containing cyclohexane ring.
1O. How many structural isomer are possible for C4H10O (only alcohol).
LL. Number of structural isomer of C6H1a is .

12. (a) (x) ( Number of plane of symmetry)

-)
cH2-cl

-
(b)H-_____J(y)(Numberofmesoisomerof1,2-dichlorocyc1opentane)
CI CI

Sum of (x+.y:71

L3. Find out the total number of stereocentre in the given compound.
CH?-CH: CH__CH-CH-CH3
lt
Br Cl
'1,4. Find out the total number of stereoisomers of the given following compound.
CI
I
CI-CH: CH-C-CH: CH-CI
I

H
L5. Find the total number of isomers of C7 H14 (only S-membered ring).
16. x :nurlber of compounds which undergoes Tautomerisation to form an Aromatic product.

o o o o
It
,"r# (b)
(\
V (c)

I
H
 (e)
'}
9oo
{ }
-7: \-

Jl
\-/ I
\/
(D Ff
il
tP
I
Gl
+ (h)+
tr
N_G_H-

17. If molecule is pyramidal, X stereoisomers are possible for :

G abed
find the value of X.
 1. a-q;b-p;c-r;d-s 2. a-s;b-r; .-q;d-p
3. a-p, b-e, r, si c-9, r, s; d-p, S
s; 4. &-p, q; b-p, ei c-p, q; d-p, t
5. a-r;b-r; c-p; d -s 6. d-p,r; b-g, Si C- g, ri d-p,,
7. ?-e, r; b-9, si c-p,9, r; d-q, s 8. o-r, s; b-p, Qi c-r, Si d-p, r, s

9. a-q; b-q, s; c-p, e, Si d-q, s 1O. a-p; b-q; c-s; d-r

11. 12. o-q,r;b-pic-p;d-q,r
"-p;b-q;c-r;d-s
L3. a-r;b-s;c-r;d-p 14. a-s;b-r;c-q;d-p
15. u-q, r; b-r, s; c-9, ri d-p, q
16. (a-p-x); (b-q, r-y); (c-p-x); (d-q, r-w)
17. A-b,h; B-zl,9; C-c, e; D -d, f
18. A-d;B-a
19. a+b +c+ d=L3
20. A-b, d, e; B-d, C, f, h; C-i, k, p
21. A-e, lj; B-fl, c, d, g, h, i, b; C-None
22. w+x+y+z=L2
23. A - (c & e), (b & d); B - (a & b) or (a & d); C - (a & c) or (a & e), (b & c), (b & e), (c & d) and
(d&e)
24. A- (agc) (b&0; B-(a&d) or(c&d), (a&e) (c&d); C-(d&e)
25. a-True; b-True; c-True; d-False
26. b, e, f, B, h, i
27. A- d, h; B -d; C - f, h; D -h
2S.CompoundABC
Icaa
IIcbb
mcaa
IVcbb
Vcaa
VIcaa
VIIcaa
VIIIebb
IXeaa
Xebb
2s. ta) @ G)@
3OA. 1 -N; 2-Z;3-E; 4-Z;5 -Z;6-E; 7-N
B. (a) 1 -Z;2-E;3 -E;4-Z;5-Z;6-E (b) ze (c) 10
31. l-Z;2-N;3-E
32. (a) A-10,F -4,C-2 (b) A-5,B-0,C-5
(c) A-4,E_-2,C-O (d) A-2,8-1,C-0
(e) A-5,8-2,C-l (D n-4,F--7,C-2
(S) A-4,8-2,C-0 (h) A*4,]8_-L,C-2

33. (1)

(3)

CI
Br MesC-J'
(s) C1

r
(6)
2 CMe3
(7) C, axis, C, axis (B) Cr-axis

;fl

tst @ uri'
"r&
(1 1) (12) Cr-axis (13) Cr-axis
 (R

r)
S)
H I{(CH3)2
S)

o (s
(R)

3.4. (1) NCH3

morphine

('
NH. o (R)
rL N
H (R)
N?g;

(3)

amoxicillin

(s)

zocor

35.
Identical Enantiomer Diastereomer Constitutional

V\7
Isomer

(1)

iA
co2H co2H

(2) ,/,n
 QHg Et
(4) H#oH
I Ho-l-,
HtoH r-ro-Fn
Et cHs

(e,d&"u
,rrry&-x
 36. (A) - (d) (B) - (b)
3-7.a-p;b-q;c-r;d-s
38. a-s;b-p;c-q;d-r
H
3e. H€EH
(Resonance) r-(vacant-p-orbital)

40, (1) 16 (2) 4 (3) 16 (4) 4 (s) 4

(6) 4 (7) 4 (8)3 (e) 4 (10) 4
(tt) 2
4L, &-2, b-4, c-3, d-4, €-8, f-2
42, a-s;b-p;c-q;d-r
4g. d-25, b-2s, c-27 *23, d-29
44. A-e;B-b;C-d;D-a
45.. A-e;B -c; C - a; D-b; E-d
46. z-p,9, S, ti b-p, t; c-P, q, r, s, t; d-p

Subjective Problems
1. 3 (c, f, h) 2. 64 3.5 4.5 5.2 6. 8. 7.3
8.6 9. 12 10. 4 11.5 12. 4 tg. 4 t4. 4 15. 8
16. 4 (a, b, c, h) 17.6
 reffi

Hffi 'ffiCffiEffi

L. What is the major product of the following reaction ?

HgoCI
>

*,er;_..,
cHs

cH2 - oH

.,CT:J,, ,r,tH,
CH"
. l-t-ocH3
2. I
Ul tar, -ffiil(P) Product (P) is:

'o 'll- cocH3

 CHc O CHq O

,:,)aY8-on
\ncH2_[o.",
,0,ffl-'n
' - \'
' cHz-cocH3
o
CH" CH"

(') .+f-oh ,0,fffi-ocH3

L
-, [&, - cocH" \ c;,_f _on
cHs- $ o
oH
sH
lxcH3MgBr
- z Hf.--+ oH *,l.
AAaJ<:X:
3. Reaction- 1 ; .-cHz
l-cH=
OH
OH
I

c-o-Et cH:-c-cH"
"

-\ 1 ,,.Lr \.rfta. ,/---'

Reaction-2; fQ] fQ]

Y
. cHz-cl^1
Y.,
What is the ratio of (x/y) in above problem ?

(a) l.s (b) 2 (c) 2.s (d) s

4. In which of the following reaction 2" alcohol is obtained as a product ?

rtt )-**.,
rut cHJo
", J+#H.- (2) H2O

(c)
\1' *-11)-{I4e- (d) Both (a) and (b)
,l
5. What product would you expect to obtain from Grignard reaction when an excess of
phenylmagnesium bromide reacts with dimethyl carbonate CH3OCOOCH3 ?
o
OH
tt
OH OH
ll

-CH- Ph
I

(a) CH3 (b) CH3 (c) Ph-- (d) cHs c-_ Ph

-C --
Ph oh
I- -
I

Ph ir,
 rii*)#i.I#l#tiry3tpi.i'1i-i.::li?ii'1r! :i iiiiiil+l:.rilr::i:

5. In which of the following reactions product formed is same ?

MeMsX
" >P (ii)V
r>" FMdrp

(iii)
Y \lN4ggr ------+ P

(a) (i) and (ii) (b) (ii) and (iii) (c) (i) and (iii) (d) (i), (ii) and (iii)
7. Which of the following reaction sequences would be the best for synthesis of 2-pentanone ?
o
(a) cH3-cHz-cHz- I H tT,rTr', Hgoo,
- Et2O
CH"-CH"
(b) l' l" tErY" Hsoo
)
o
cH3-cH
-
Et2o

(c)CHg-CHz-CHz-C-N tFY'r Hsoo

>
Et2O
o
tIiT" ,
- A- n
(d) cH3 cHz Hgoo
- (ProPanal) Et2o
>

OH
I
co2cH3
x CH"Mgl ,z\.zC(CHg)z
lO I
co2cHs
H*
\n!(cHr2 ,Dimethylphthutut.
OH
Number of moles (x) of Grigaard reagent consumed in the above reaction is :

(a) 2 (b) s (c) 4 (d) s

OH
I
I

9. Ph- C- CH3
I

cH2 -cH3

\tVhich of the following combinations can not be used to prepare alcohol given above ?

o
il
(a),PhMgBr * 2-butanone NH4ct
+ (b) EtMgBr + Ph - C -CH3 -
NH_ct
o o
il
(c) CH3 MgBr + Ph - I -r, -*H
NH4CI
(d) EtMgBr + Ph - C -CH2 - CHe .r.cl -
=--+
 (1) cH3MgBr
10. Et- o- I- o- Et (A), Product (A) is
rrffi+ :

o o
il
C- O-
- c-
il
(a) CH, Et o) cHs cH3
- OH
I

(c) CHs -C -CH3 (d) cHs cHz cHs

I
- -
cHs
o
oAo H* , (A). Product
11. PhMgBr+ I (A) is:
excess \.., )
o OH oHo
o) pn-c- '/\'/ I oAA
il
(a) Ph- C-
I

Ph Ph (c) Ph - J (d) Ph
I I

Ph Ph
olt
12. ( O)-i
\-Y - NocH.," * cH3MgBr
-=;-;+
'"ilro
(P). Product (p) is :
I .Methvleasnesium
bromide 75 equivalent
>9oo/o
CHS
N-Methoxy-N-methyl
benzamide 1 -equivalent

OH OH o o
(a)
I

Ph- C_ G) pn-t-.r. I

(c) Ph- C-
il
CH3 (d)
il
Ph- C- Ph
ln CHs

13.

d
Point out the incorrect synthesis :

OH

,rr(,
^.,/MgBr #
fl

OH

.rq (1) Mg,ether

--_-------------
(2) Ph-CHO
(3) H3oe ErCH_Ph
I
I

H H
$ffffi
CH, - CH"

(c) phMgBr + r'))q1 ,ph- cHz cH2 oH

(2) H- - -
(1l,nfTo
(d) PhMge. + (2) H"
> Ph- cH2
- oH

o
14.
il ,o
,1a1- ri)!!Ue\
- t- o- ,
CHs NaHCoe
1g;
(gas) (ii) H3Oe
o
ll
S- NaHCoa
,o
(C1 (i) Phlugqr
- Ll O- H
CH: , , ,r,
gut (ii) H3os
o
Product (B) and (D) in the above reaction are :

oo o o
ilil
(a) Ph- C- o- H. ph- S- o- H
il
(b) Ph-C-O-H, Ph-S-O-H
il

il 74
o
oo o o
ilil
(c) Ph- C- O- H, ph- C- O- H (d) pn- c- il
oH, Ph- S- O-
il
H
74 74
(1) MeMgBr,
ls. ><x,
THFOOC
(A); Product (A) in this sequence is :

(r)ryot'
--+
"''.,0,
,,,

o
$" %",,., W,0, Q*
-\
16' (4.r, offiffi.-F Products

Comment on optical activiry of the products. Thev are :

(d) racemic mixture (b) diastereomers

(c) meso forms (d) opticallv inacrive due to absence of chiral cenrre
 HBr rn water
(a)

(c)
ffi d"', (d) Ar,",,n",:

Hrsoo (B), product (B) in this reaction

18. r'an ,A
(1) 2phMgBr
> is
\*oAo Q)Hzo
:
a
18

,",
O(\* OO G)
18
ph,., @g ra,
OO i*
19. All of the following compounds react with ethylmagnesium bromide. Alcohols are formed
from three of the compounds. Which one does not give an alcohol ?
o o
(a)Gl, ",G8o.,,
o
il
,, Ph-o-c-o-H
G.rro[.t, (d)

20. A student was carrying out a Grignard reaction between PhMgBr and ethyl benzoate. She ran
out of anhydrous ether just after the Grignard reagent was made. Which of the following
solvents can still be used to dissolve the ethyl benzoate for its reaction with already formed
PhMgBr ?

(a) acetone (b) ethyl acetate (c) absolute alcohol (d) benzene

2r.
zt'
*.or.. ..lAl - ?1 X.-,-r,
a
(1) xPhMgBr HO
_-_----..-.?
\tBu

,oN (2)H3o@

Number of equivalents of Grignard reagent (x) used in reaction (1) is :

(a) 3 equivalent (b) 4 equivalent (c) 5 equivalent (d) 6 equivalent

 1',
fr" (l)Mg;ether aycH-Ph
22' \*/ .tph-cHo--+ (*)
(3) H3oe
| 'i
HH
The given product can not be obtained in the above reaction. Identify the correct product
obtained'
1" ?
.
,",[-nlo"-on",O ,rg*-on,o, (-jcH-Ph
H
tli OH CH-Ph

2g. Which of te following gi.8rHffo isomers of 3o alcohol, when treated with phenyl
magnesium bromide

,,,+ ",+ ,,Q

?

,.,H
oo0o
*t., ol' .r'
24. ( . ) lv{eN'lgBr '
, Product of the reaction is
\<
:

HPh
Me Me

,"r*H: .',TH:, (c) Both (a) and (b) (d) None of these

Ph Ph

2s. RMsBr
, product; The product of the reaction is :

U
/\
(a) HSO2 (b)H-SO2(CH2)3
-CHz -CHz -CHz -CHz -R -R
tc) [-l-- ^
\_ -/iugnr
(d) H-so2(cH),
-R
SOz
,
26. When carboxylic acid reacts with organolithium reagents to give ketones, side reaction
' sometimes occur. For example,
 o CHs
til,
HocH2cH2cHCHrcHrc oH *Ft'
,'.]
!"1t' , rt2 ,
tetrahydrofuran
cHs o
I il
HOCH2CH2CHCH zCHz-C -CH3 * compound (B)

Compound A 630/o 37o/o

Value of (x) in above reaction is :

(a) 2 (b) s (c) 4 (d) s

27. Which of the following alcohol can not be prepared by the reaction of acid chloride with
excess of Grignard reagent followed by acidification ?

OH OH OH OH
(a) Ph--l-nn
I
6; nn{cH,
I
(c) rrf* ra) cH;f nt
cHg cHs cHs Ph
o

2s.
ffi*ffi-ra)-*-+,ji1,,
Product (B) of the above reaction is :

QHz

(a) (b)

(d)

29. The reaction of elemental sulphur with Grignard reagent followed by acidification leads to
the formation of
(a) mercaptan (b) sulphoxide (c) thioether (d) sulphonic acid

30. t-l + MgBrcH2cH2cH2cH2MgI3,

e_____2.___z -H- product; product of the reaction is :
1ii)Hro+
\AO
o
(a) Ho U
- (cHz)s - I -cHz- cHz--cH3O),ora,aH2)3 _ oH

(c)*,Xr-cHz-cHg
I

OH
(d)
H R z- cHz- cHs
 cl(i) xi'HrJraser,
Br. fAfc -
\*c_cl (ii) H+
il
o
Me
Number of moles of CH3MgBr consumed in above reaction is :

(a) 2 (b) 4 (c) 6 (d) 8

32. End product of the given reaction is :

U''-#- (A)-ffiffi-+(B)

,,,efo" (b)Oa"'
(d)o
33. Which of the following compound is not a suitabie solvent for Grignard reaction ?

,, fJ(THF)
(b) (")
(i, 4-dioxane)

(c) CHg (d)

-O-CHz -CHz -O-CH3
34. /'r Et't
predict major product of the reaction :
'(2 mole) -Ye.---
(d),,A\,,A'/
35. Which of the following reaction sequences would be the best for synthesis of t-buryl alcohol ?

o
(a) cH3cH2MgBr
,1-\CH' Etzo ,
+ iHr- Hro@ ,

(b) CH3CH2CH2MSBT
-ffi-+ --rl@--
o
(c) CH:MgBr+CH3
ll Hgoo
-C-CU, --E!u9-+ >

?
(d)CH3CH2MgBr+CH3-e-H E'o > Hsoo ,
36. What is the major product of the following reaction ?

Hsoe
CHs
-C: *-!*HL >

,/
N
il
(a) CH3 CHz NH CHs (b) CHs-C-CH3
- - - o
o
il ll
(c) CH3 (d) cHs
-C-CH3 -cHz -c-oH
gr. " -a 'zcHg (1) PhMsBr products; product
> obtained in this reaction are :

ll rzl u*
o
(a) diastereomers (b) racemic (c) pure enantiomer (d) meso
38. CH3CO2Et + (CHr)s(MgBr) z 121 u-:+a"..lioO
: compound (A) will be :

-\'ou
,rr(, ,r,d,
o
(c) CH3
il

-C-(CHz)a -CH3
(d)o
o
il
C_Ph
(1) PhMgBr/cucl
(2) U+
, (A) ;A will be :
cleH2oo

otloO
-\ oh o
ll ll -, il
-
o)eI:-" ,.,eIk'n
Ph
-^-r'C
,",c)'"I"'" (d)

V Ph

-'"qoMe n-Bu 2Cu Lt

4,-' (n-Bu=n-butyl group)
Product of the reaction rvill be :
 OMe
(c) ,o,*xI""
41. t'-[-o-*' , (?) ; product of this reaction is :

,Jff'
ff'
,,,ffo2Men,O ,ro
42. Ethyl acetoacetate when reacts with one mole methyl magnesium iodide then product of
reaction will be :

oo ooufiu. o
(a) CHs
ll il lil
(b) cur-g-cHz-c-cH3
-C-CHz -C-CH3 I

CH"
o o"
il,
(c) CHe-a-3r-corEt (d) cH;
il

-c-cHz -co2Et
MsBb
lt
43. C$3MgBr + EI-O-C-O-EI t'(2) (A); ProductA is :
(excess) He
OH
o OH

rutNoH b)^ (.)A (d)

I

For the sequence of reactions, o -*.#L B H2olH- > tert-Pentyl alcohol. The
compound A in the sequence is :
(a) 2-Butanone (b) Acetaldehyde (c) Acetone (d) Propanal
O
lt (1) excess CH3-Li
45. PhMgBr + CH3 -CN-H_,"*-+ (A) Ph -C -O (2) H3O

Same product (A) will form in both reactions. A is :

,-oHo
(a)
rll
Ph-9-CHs (b) Ph-CHO (c) Ph-C-CH3 (d) Ph-CHz-Co2H
I

CH,
* ..'.' "'" ' l'll':ilillllll,l:irlr:1r,."lir''

;,'l"t:;i,.t#Sii
"
46. Which of the following Grignard reagent can be prepared ?

(a) Br Mg O H (b) Br Mg
- -CHz-CHz-CHz-
(c) BrMg CHz CHz NHz
- (d) Brtvtg
- -CHz -CH2 -SH
- - - -CHz -CHz - I -CH:
47. In the reaction sequence :
cHs
o

o (i) CHsMgBr/CuCl

0o
(ii) H2O/H+
Product (X) will be :

,"rtU ,,,tr:", ,.,&::' ,.,"U:",

CHsMgBr(excess)
48. (C2HsO)2CO
HsO*
A. A (alcohol) can also be obtained by :

o
CH3MgBr(2mol) il CH3MgBr(2 mol)
(a) CH3CH2CHO (b) CHaCOC2Hs
Hso- Hao*
o
ll
CHstCHs cH:MsBr (lmol)
(c) , (d) as in (b) and (c)
Hso*

49. The princip-al product of the reaction ber"areen methyl butanoate and 2 moles of CH3MgBr
after hydrolysis is :
(a) C3HTCOCHg (b) CgHzC(OH)(CHr y,
(c) C3HTCHOHCH3 (d) CsHTCOCH(CHa )z
50. Which of the following compounds will form hydrocarbon on reaction with Grignard reagent ?

(a) CH,CH2OH (b) CH3CHO (c) CHTCOCH3 (d) CH3CO2CH3

51. What is the product (B) of the following reaction sequence ?
Br
.W-*#o
A+' 8, (1)Et2o
(2)
>B
H3oo '
u
\J"'ttCH3

9H
\ :

(^)
O4oH, ,0,
52. Which, if any, of the following pairs of reagents could be used to prepare 2-phenyl-2-butanol?
o o
il
(a) CH3CH2MgBT + Ph (b) CH3CH2MgBT + C6H5CHrIH
-C-CH3
o o
il il
(c) CHsMgI + C 6H5CH2C CH3 (d) C6HrMgCl + CH3 CCH2CHzCH3

53. \,Vhat is the product of the following reaction?

\oAo + 2cH3 MgBr -.ffi--

-,^^l't
Product

| - ' 'l
(a) HO - CHC H,CH,CH, CH - OH (b) cH3ocH2cH 2cH a TCHC Hs 2CH
' 'l
CHs CHs OH
cHs
I

(c) HOCH2CH2CH2CH2 C
- 'l -
OH (d) HOCH2CH2CH2CHzfUOCH'

cHs CH:

Ph
54. ,- t' scHo
, a ; Product (B) is :

Br -rylg+
ether 2. H*

(a)lYo' :-
CHz
- OH
(b) Ph-C C:
-CH2 -CHz -CHz -OH
(d Ph-C:C-CH2-CHz-OH
(d) Ph : C
-CHz -C -CH2 -CHz -OH
bb. What sequence of steps represents the best synrhesis of 4-heptanol (CH3CH2CH2)2CHOH ?

(a) CH3CH2CH2MgBT(2moles) + formaldehyde (H2C = O) in diethyl etherfollowedbyH3O+

(b) CH3CH2CH2MgBT * butanol (CH3CH2CH2CH =O) in diethyl ether followed by H3O+
(c) CHTCH2CH2CH2MgBT + acetone [(CHs )2C =O] in diethyl ether followed by H30+
(d) (CH3CH2CH2)2CHMgBr*formaldehyde(HzC =O)indiethyletherfollowedbyH3O+
o
Etil
s6. \-/\-/
s\
HMe
-tffi- comment on srereochemistry of products :

(a) diastereomers (b) racemic

(c) single stereoisomer (d) meso
 cH2- OH

57.
I

CH
-OH
+ CHrMgBr
---) dH+
tn,- rn
(Excess)

What is the value of x in the above reaction ?

(a), ,r, ,
(c)s @)+
0.40 g of an organic compound (A), (M.F._ CsHsO) reacts
with x mole of CH3MgBr to
liberate 224 mL of a gas at STp. With excess of H2, (A) gives
pentan-1-ol. The correcr
structure of (A) is :
(a) CH3
(b) CHs
-C - C -CH2 -CHz -OH
(c) H
-CHz -C - C-CH2 -OH
-C - C -CHz - CHz - CH2- OH
(d) H-C-C-CH2-CH-CH3
oHo
59. cHs cH : cH,
'"' lt' n" , .r"-t-."" ,
, --D,r=rh.,-
- ;*. :;;' ffi E

-+--, .jLJ.
(major)

End product (lJ of the above reaction is :

CHz

(a) CHz : CH CHz

- -8 -ar,
(b) H2C :CH --CH :f _an,
cHs

OH
(c) H2c : cH
- cn,-l
-4 -cHs
CHs
(d) HzC : CH-CHz
-CH-CH, -OH
t,;
tt=,,^
- t.
60. CH, CH CH,z' ,tal_!E{_+Cfl;
- - ?rv ' \'L) product (B) is :
\/ "ttane

(a) cVH-cH2-cH3 (b) CHs

-O-CHz -CHz -CHs
(c) H2C:CH-CHz-O-CH3 (d) HzQ
- cH -
\o/
cHs
61. Compound A was treated with a large excess of CH3MgBr. The resulting product was
exposed to POCI, /pyridine to give compound B, as one of many products :

Which of the following compounds can be A ?

oo
(a) H

62. Identify product Z in the following reaction sequence :

1. C6H5MgBr,
: diethvlether
H 2C CHCH rer --Ie!I-+ , 2. H3Of
, 7

o o
(a) H2C : il
CHCH2CC6H5 (b) H2C:CHCH2NHCC6Hs
rl

OH NHz
(d) H2C : CHCH2CH C6Hs
I

(c) H2C:CHCH2CHCoHs

CH3MgBr
#

CI

(Consider all steps and intermediate) correfi statement is :

(a) Nucleophilic addition (b) Nucleophilic substitution reaction

(c) ,Product obtained is chiral (d) All
 which combination(s) of alkyl bromide and epoxide
can be used to prepare the following
product bv addition of the Grignard r.uj."ia.;i;; fr;*. *firomide to the epoxide ?

'"'G A o
*,e[-,.,4
(c)

65. What will be the final major product ?

rus cH'-I>1r1
#o '111
18

o .sI
(b)A
SHi
(c),,#\,0,*,fi
66. Give the expected product of the following reacrion.

1. MeMgBr (excess)
2. HzO

",Jreq
,,T:frO(:;
 1r (b) 2. (d) 8. (b) 4. (d) 5. (c) 6. (d) 7. (c) 8. (c)

9. (d) L0. (c) 11, (b) 12. (b) 13. (b) 14. (c) 15. (b) 16, (b)

17. (d) 18. (d) lg. (d) 20. (d) zil" (c) 22. (b) 28. (b) 24. (c)

25. (c) 26. (b) 27. (d) 28. (d) 29. (a) 30. (b) 31. (b) 92. (b)

$3; (d) 3,4. (b) 85. (c) 35. (c) U^7. (b) 38. (b) 39, (b) 40. (a)

41. (b) 42. (c) 43. (b) 44. (c) 45. (c) 46. (d) 47. (b) 48. (d)

49. (b) 50. (a) 51. (a) 52. (a) 53. (c) $4. (b) Dt. (b) 56. (a)

$7. (c) 58. (c) 59. (b) 60. (c) 6r. (d) 62. (a) 63. (d) 64. (b)

66. (d)
___l
 ::
&riglrlo;rd fteegunf,,

Grignard reagent is usually prepared by

Et2o
R-x + Mg )RMgx Grignard reageht
Etzo
Ar-x+Mg ,ArMgx Grignard reagent
Grignard reagent acts as a strong base. Grignard reagent carry out nucleophilic attack in
absence of acidic hydrogen. Grignard reagent forrn complex with its ether solvent.
Complex formation with molecule of ether is an important factor in the formation and
stabiliry of Grignard reagent.

A. What is the correct order of reactiviqv of halides w'ith magnesium ?

(a) R-Ci>R-Br>R-I ft) n-Br>R-Cl>R-I

(c) R -- I > R- -- Br > R--Cl (d) R - I = R - Br = R -Cl
B. Which of the following will undergo acid-base reaction with Grignard reagent ?
(a) HC = CH (b) R -oH
(c) R -CO2i{ (d) All of these
C. Which of the fbllowing reactants give primary alcohol as a major product when reacts with
RMgX followed by acidification ?
o
il
(i) cH,
x/'
-
o
o
cH. (ii) H-c-H (iii) Cu,
\./ -
o
CH
- CHg

(iv) CH3 - C-^H

il
(v)
I] (,i)G
(a) i, ii, v (b) i, ii, v, vi (c) ii, iv, vi (d) v, iv, iii, vi
O
ti
D. cl - t -o - Et - (1) xRMgX ,30 alcohol. value of x is :
t" *n'l'',
(a) 2 , (c) 4 (d) s
o OH
il (1)xPhMgBr
H-o -cHz-cHz -c-o-Et
I

E.
(2) H+
,Ho-cHz-cHz- C -Ph, Value of x is :

Ph
(a) 2 (b) 3 (c) 4 (d) s
,+.i$mm

F.
(a) HS -CHz -CHz -CH2MgBr (b) HO -CHz -CHz -CH2MgBr
(c) NHz -CHz -CHz -CH2MgBr (d) All of these
G. How many different Grignard reagents when react with EIOH, give n-butane as product
(excluding stereoisomerism).
(a) 1 (b) 2 (c) 3 (d) +
Match the column I and II.

o
lt
Et Ph - CHz OH
P,hMgBr+ Cl
(excess)
- C -O - ,n -+

Fh *CH - Ph
PhMgBr+H-C-O-Et ,*+ OH
I

OH
o I

Ph-C-Ph
I

lt
PhMgBr+H-C-H He
>
-
I
(excefs) Ph

PhMgBr+ CHs * C -O - Et ;;--+

(excess)

Match the column I and II.

oo
PhMgBr + (A) *H.?l"alcohol ilil
CH" 'C*CH" -C-CH
o
PhMgBr + (B)
- Ho---+
2oalcohol
I
t[:
C:CI{

PhMgBr + (C) --.--+ 3oalcohol

lfi iil phMgBr + (D) --H.---+ O

Match the missing reactant A, B, C, D
 t' ,i l' .:' r. '::'

4. Match the column I and II. (Matrix)

5. When 20 g of a compound (A) (M.F. = CaHl6Oa) reacts with excess of CH3MgBr, 14.6 L of
CHa is obtained ar STP. What is srrucural formula of (A) ?

cH2-oH cH2oH
I

(a) (CH oH), (b) HO

I

t- -
cH2- oH
-CHz-c-cH2oHI

OH
HO\ .OH

(c)ll toH
(d) Both (a) & (b)
Ho/
 SUBJEGT]VE PROBLEIIS

1
I.

,ry;XfT-=+,o
How many geometrical isomer of (D is possible ?
2. How many isomer of CaHsOwhen reacts withCH3MgBr followed by acidification to give 20
alcohol (only consider carbonyl isomers)?
(including stereoisomer)
3.
Total number of RMgX are consumed in the following reaction

-+
xRMsX
o\t,.z

A o

4. How many isomers of CoH,sO reacts tr.ith CH3\IgBr to er-oh'e CH. gas ? ( Excluding
stereoisomer)
5. How many carbonyl isomers of C rHlsO which reacts with Ph\lgBr to give racemic mxrure ?

6. How many moles of Grignard reagent will consume n-hen it reacts rvith following
compound?
cH:o o
ll
HO C-CI

H-S C-O-Et
lt
C o
llt
N
 1. A-c; B-d; C-a; D-b; E-b; F-d; G-b
2. a-r;b-q;c-p;d-s
3. a-s;b-r;c*q;d-p
4. a-r;b-q;c-p;d-s
5. (d)

Subjective Problems
l. 4 2.2 3.7 4.4 5.5 6.8
 irii i! iii,iii ii :lliiiiiiiiiiiiiii,'

ffi ffiffi,

1. On halogenation, an alkane gives only one monohalogenated product. The alkane may
be:
(a) 2-methyl butane (b) 2, 2-dimethyl propane
(c) cyclopentane (d) both (b) and (c)
2. Which of the following compounds can be best prepared by Wurtz-reaction ?

(a) Iso-butane (b) n-butane

(c) n-pentane (d) Iso-pentane
3. A hydrocarbon A CV.D. = 36) forms only one monochloro substitution product. A will be :

(a) iso-pentane (b) neo-pentane

(c) cyclohexane (d) methyl-cyclohexane
4. Ethyl iodide and n-propyl iodide are allowed to undergo Wurtz reaction. The alkane which
will not be obtained in this reaction is :
(a) butane (b) propane
(c) pentane (d) hexane
5. CH"-
'
CH
- CHz-
z CH,r --fi:----+
h'
I
,, l--
CHg
Number of chiral centers generated during monochlorination in the above reaction :

(a) 1 (b) 2 (c) 3 (d) 4

 ,,,r;llii:t, j :i::::liii;rii:ir!iliirl

:i'Iiiffilifrffiirt ;lili*'llfiffi
6. CH3C1 --+ CHo
Above conversion can be achieved by :

(a) Zn / H* (b) LiAtH4

(c) Me / (ether) then HrO (d) all of these
7. n-Butane cl'z/hv ,
Give the total number of monochloro products(including stereoisomers), which are possible
in the above reaction.
(a) 2 (b) 3 (c) 4 (d) s
8. CHo + Cl, --!5CH3C1 + HCI
To obtain high yields of CHrCl, the ratio of CHo to Cl2 must be :
(a) high (b) low
(c) equal (d) can't be predicted
9. Double bond equivalent of cubane is :

Cubane
(a) 4 (b) s (c) 6 (d) 7
10. How many bond cleavages are required to convert cubane into non-cyclic skeleton ?

Cubane Non-cyclic skeleton

(a) 2 (b) 3 (c) 4 (d) s
L 1. Draw an energy profile diagram for a three step reaction in which first step is slowest and last
step is fastest. (Assume that reaction is exothermic)

progress of reaction progress of reaction

PE
(c) (d) None of these
/\

progress of reaction
 i+rffiiiii+fi iffiffiffiffi,,;ffi'
1r2. CH3-CH-CH2-CH, -*--> (x) Number of monochloro product including

CH.
stereolsomers.

(a) 4 (b) s (c) 6 (d) z

ND.-ND"
13. Hzoz
--(t't\
Product (P) is :

(a)l
\.,,/ I ^\<DI
G)L.t, D
(d) both (b) & (c)

Hz(lmole)/Pt,
14. 141
Double bond equivalent (degree of Unsaturation) of (A) is :

(a) 1 (b) 2 (c) 3 (d) 4

15. Arrange the following alkanes in decreasing order of their heats of cornbustion.
cHs
(i) cHs-T-.n, I
(ii) cH3- QH -cH2 -_CH3
I

cHs cHs
(Neo-pentane) (i) (Iso-pentane) (ii)

(iii)cH3 cHz cH2 cH3

- ;,_!k; -
(a) (i) > (ii) > (iii) (b) (iii) > (i) > (ii)
(c) (iii) > (ii) > (i) (d) (i) > (iii) > (ii)

16. t]rl * Hz Pd >

Y\H,
cHg
Product of the above reaction wili be :

(a) Racemic mixture (b) Diastereomers

(c) Meso (d) Constitutional isomers

300"c
47. CH, + Brz

'
l'
cH2-cH3
Which of the following compound will not be obtained as a pr,:duct in the above reaction ?
ITTDROAITBOtrS (4I, J
CH"

cH2 cH3
- cH2
- cH3
cHs

Br
(d)

cHs cH2
-cH3
L8. Following are the stnrctures of four isomer of hexane. Among the names given below, which
correctly identifies the fifth isomer ?
cH 3cH 2cH 2cH 2cH zcH (cHs)3ccH2cH3
(cH s) 2 CHCH ,CH ?CH 3
' (cH: )2CHCH(CH3 )2
(a) 2-Methyl pentane (b) 2-Ethyl butane
(c) 2,3-Dimerhyl butane (d) 3-Ivtethyl pentane
19, Which of the following describes the best relationship berween the methyl groups in the
chair conformation of the substance shon-n belorv ?

cHs
cHs

(a) Trans (b) Anti

(c) Gauche (d) Eclipsed
2a. compare the stabilities of the following rwo compounds (A) and (B):
A : cu- 1-ethyl-3-methyl cyclohexane B : tans-l-ethyl-3-methyl cyclohexane
(a) A is more stable (b) B is more stable
(c) A and B are of equal stability (d) No comparison can be made
21. Which conformation of ethane has the lowest potential energy ?
(a) Eclipsed (b) Skew
(c) Staggered (d) All will have equal potential energy
22. Ethane is subjected to combustion process. During the combustion the hybrid state of carbon
changes from :
(a) spz to sp3 (b) sp3 to sp
(c) sp to sp3 (d) sp2 to sp2
23. CHe CH, CHz CH, CH CH3
- - - -a\CHe - I
-
cHs
Above reaction is an example of :
 :1 :rti l:i:rt::tiil:i1t:1i i;t: i:tij ti iji iitii 1: i llt:,r r:: j : ii r iiij :iiji:ii i ii]lti I t: ii

(a) isomerization (b) polymerization

(c) cracking (d) de-hydrogenation
24. which of the following has highest chlorine content ?
(a) Pyrene (b) DDr (c) Chloral (d) Gammaxene
Pure methane can be prepared by :

(a) Wurtz reaction (b) Kolbe electrolysis method

(c) soda-lime de-carboxylation (d) reduction with H,
Calcium carbide * heavy water ---+ ?
The product of the above reaction is :

(a) CrH, (b) CaDz (c) Ca(oD), (d) cD4

27. cHe-*r{ cHs-.rr-O cHs-.rr-O

Ethyl cyclopentane Ethyl cyclohexane Ethyl cycloheptane
(D (II) (IID
Arrange the compounds I, II and III in decreasing order of their heats of combustion:
(a) II>I>III (b)t>II>rII
(c) III>II>I (d)ttt>I>II
28. An alkane (mol. wt. = 86) ol bromination gives only two monobromo derivatives (excluding
stereoisomers). The alkane is :
CH,
(a) CHs- C H
-CH, -CH2 -CH3
(b) cHr-g-cHr-cH,
I

I I

C H3 CH,
CH,
(c) CH, I
(d) CH,-Q-CH,
-
CH
lr
-CH -CH,
CH, CH,
I

cHs
29. Order of the bond strength of C H bonds involving sp,sp2 and sp3 hybridized carbon
atoms is :
-
(a) sp >spz >sp3 (b) sp3 >sp2 >sp
(c) rp' > sp3 > sp (d) sp2 >sp> sp3

30.

(r) (II)
Q,Q,@
Arhong the structures given, select the enantiomers :
(m)
HHCHSHHCHg

(a) I and II O) I and III

(c) II and III (d) I, II and III
 -.r,ll:i.:.ll.rj.'l'..,,.1,.".,1..',.'..'.,..'..:,,:...

f,qq{+fi$ffi:{$f |
.' .,.it.:::r,, : .:r
rft"

3L.
A (r) (II)
o (III)
The correct order of reactivity of I, II & [I towards addition reactions is :

(a) I>III>lI (b) I>II>III (c) III>II>I (d) III>I>II

Na/Drv ether
32. D---S (A)
97o/o

Product (A) of above reaction is :

",Q *r+ ,ro

33. Which of the following reactants is suitable for preparation of methane and ethane by using
one step only ?
(a) HrC : CHz (b) cH3oH
(c) CH, Br (d) CHg
- -CHz -OH
How many carbon atoms does an alkane (not a cycloalkane) need before it is capable to exist
in enantiomeric form ?
(a) 4 (b) s (c) 6 (d) 7

35. Among the following free radical bromination reactions, select those in which 2" halide is the
major product
- cH2-cH3
Brz/hv, Brzthv,
Brzlhv,
(P)
n (a)
a
(R)
O

(a) P, Q, R, s (b) P, R, U (c) P, R, S, T (d) P, Q, R, S, T

36. (A) + cI, monochloro product

-\,the yield of monochloro
To maximise product in the above reaction ?
(a) Cl, must be added in excess
(b) Reactant (A) must be added in excess
(c) Reaction must be carried out in dark
(d) Reaction must be carried out with equimolar mixture of Cl, and A
37. cHs cH, cHz cH,
- - - -I3zh5
Major product in the above reaction is :

(a) Racemic mixture (b) Meso

(c) Diastereomers (d) Constitutional isomers
38. Select the chain propagation steps in the free-radical chlorination of methane.
(1) Cl2 ---) zCI' (2) Cl' + CHo
---+ CH3CI + H'
(3) Cl' + CHo (4) H'+Clr---+ HCI+Cl'
--+ CH! + HCt
(5) CHi + Clr---) CH3CI + Cl'
(a) 2,3,5 (b) 1, 3, 6
(c) 3, 5 (d) 2,3, 4
9H,
aA. Br,/hv
39. Monobromo derivarives
(, ---+
The number of possible monobromo products is (excluding stereoisomers):
(a) 4 (b) s (c) B (d) to

40.
* Br.
OH -_-)

Br" will abstract which of the hvdrogen most readily ?

(a) a (b) b (c) c (d) d
4L. Arrange the foltrowing compounds in decreasing order of their heats of combustion :

9Hs O
cHs cHs
n.o'l-{2,
cH3 cH3
F=-['"'
(i) (ii) (iii)
(a) (iii) > (ii) > (i) (b) (ii) > (i) > (iii)
(c) (iii) > (i) > (ii) (d) (i) > (ii) > (iii)
42. CHs- CHr- CHz- CH2- F
abcd
Arrange the hydrogens e,b,c,d in decreasing order of their reactivities towards chlorination:
(a)a>b>c>d (b)b>c>d>a
(c) b>c>a>d (d)c>b>a>d
4iJ. on catalytic reduction (Hr/Pt) how many will give n-butane ?
alkenes
(a) 1 (b) 2
(c) 3 (d) 4
44. On catalytic reduction(HrlPt) how many alkenes will give 2-methylbutane ?
(a) 1 (b) 2
(p) 3 (d) 4
 (excess),/hv
45. I l#Clr
Horv mani-dichloro products are formed in the above reaction (including stereoisomers)?
(a) s (b) 6
(c) 7 (d) s
CH: - cH rCHs
46. ^ _. ^ H,/Pt
D,/-
(-(.t
- \D
Product of rhe above reaction will be :

(a) Racemic mlxrure (b) Diastereomers

(c) Meso (d) Constitutional isomers
47. Ph cH,
'l- cH- cH 3 --!ealr---)
-
D
Product of the above reaction rvill be :

(a) Diastereomers (b) Racemic mixture

(c) Meso (d) Constitutional isomers
cH2 cl
-
48.
cH2 cl
-
Products obtained in above Wurtz reaction is :
cHg

(b)
cHs

(c) (d) Both (a) and (b)

CH; cHs

49. Rank the transition states that occur during the following reaction steps in order of
increasing stability (least -) most stable) :

1. H3c -6 Hz+cHi + Hro

2. (cHs)ac-6nr----+(cHg)rc* +H2o
3. (CHs)rCH-6rr------)(CHs)rCH* +HrO
(a)1<2<3 (b)2<3<1
(c)1<3<2 (d)2<1<3
 ffi ffi trr+$rffi,+iffilti$j,trJi,:,'l.$iirillitil:d 1.ti1lir,r:j1j1Li!,ttri.iltiL.:ir1.1r1t:i.rillir,!r,ilt:ltiuI i-lri]....:1_:-i;I.i..i;,ir.ii

50. Which of the following does not represent major product of that reaction ?

Br

Br

(b) Br

Er
Na

dry ether

CI

(d)nr-O-sr-d,y".r,?
O

1. (d) g. (b) 3. (b) 4. (b) D. (b) 6, (d) 7. (b) 8. (a)

I

9. (b) ro. (d) Ll. (c) 12. (c) 18. (b) I.4, (c) 15. (c) 16. (b)
17. (d) 18. (d) 19. (c) 20. (a) 81. (c) 2*, (b) 23. (a) 24. (a)
25. (c) 26. (c) 27. (c) 28. (c) 29. (a) BO, (c) 3r.. (b) 92. (b)
33. (c) 94. (d) 35. (b) 36. (b) $7,. (a) 38. (c) 39. (b) 40. (a)

4x.i (d) 42. (c) 43. (c) 44. (c) 45. (c) 46. (a) 47. (a) 48, (d)
49,, (c) so. (d)
 For the given question (1, i,, 3)r,,rcnsider the following reaction.
I

O + x2-ig.+ monohalogenation product

A. Light is involved in which step of the reaction :

(a) Initiation only (b) Termination only
(c) Propagation only (d) Propagation and Termination
B. Which halogen will give the best yield of a single monohalogenation product ?
(a) Fz (b) c12 (c) Brz (d) Iz
C. How many monohalo derivatives are possible (excluding stereoisomers) ?

(a) 3 O)+ (c) s (d) 6

Halogenation is a substitution reaction, where halogen replaces one or more hydrogens of

hydrocarbon.

R-H+X, h' ,R-x+IIX

less than l kcal about tr.5 kcal
difference of E" qf.'laim.runce in E,

Progress of the reaetion,.,,

Free radical

, . :
I
t{

ffi Progress of the

rc=##

reaction, ' , ,,

Bromination is endothermic and

transition state resembles with products transition state resembles with products
Chlorine free radiCal rnakG, l,oi;'2o,3'mdi0als Tvith almost equal ease, whereas bromine free
radicals have a dear preference for the formation of tertiary free radicals. So, bromine is less
reactive, and more sdlective whereas ehlorine is less selective and more reactive.

The relative rate of abstracdot"*lr9r"rf by Br' is

troool (8-2) til

The relative rate of abstra.tps$Et"rr liycl' il
(s) (3.8) (1)
 .t-$rft

Consider the above argument and answer A to G :

A. 1-halo-2,3-dimethyl butane will be obtained in better yields, if halogen is :
(a) Br, (b) c12 (c) r2 (d) Can't be predicted
9Hg
X"/ ht'

Above product will obtained in better yield If X is

(a) Cl, (b) 12 (c) Br, (d) Can't be predicted
CH,

C. CHa- CH-
l' CH3 --!i:j]--+ Product

Major product in the above reaction is :

CH, CH,
I

(b) CH,- CH-

I

(a) CH, CH-CH, CH3

- -Cl I

C1
(c) CH,
-CH, -CH, -Cl
(d) cHr- cH- cH2
- cH3
I

CI
D. Which of the following will give five monochloro products, when allowed to react with Ct, in
presence of sun light (excluding stereoisomers) ?
(a) n-pentane (b) Iso-pentane (c) 2-methyl-pentane (d) 3-methyl pentane
CH, CH, CH, CH,

E.
ll
cHe-c-cH2-cH -cH3
Br2fhv
+ CHr-
I
I I

I
-cH,- f -CH,
fCHs
CH: Br
2, Bromo-2,5, 5 trimethyl pentane (xo/o)

What is the value of x (o/o yield of product)?

(a) IB o/o (b) 82 o/o (c) 90 o/o
(d) 60 %
F. What would be the product ratio xly in the chlorination of propane if all the hydrogen were
abstracted at equal rate ?

CH:
- CH,
- CH, --!L--CH, - CH, - CHz- Cl + CH,
- fH- CH3

C1
(x) (y)
o
(r) 1 G)!1 (c) j (d)
1

3 1 9
G. How many dichloro products (including stereoisomers) will be formed when
R-2-chloropentane reacts with Cl, in presence of W radiation ?
(a) 5 (b) 6 (c) 7 (d) B
 oclIRBOnrS f,{r,Jr&uEs}
Ci

3. A ,*i(A);
dry
Product(A)is :

\-y''o

"8: ,,,8* ,.,8 ,.,8"

/^YcozcHs H, (r
*+
more)
4. I ll (A); product(A) is :
\.'4co2cFi3 -
(a) Meso compound (b) Racemic mixture (c) Diastereomers (d) Optically active
o
ll ,r)NaoH. Cao. A
5. Ph-CHr---C- CH - -- (A)
-+
Product (A) is :

(a) Ph-CO2l-l (b) Ph-CH2-OH (c) Ph-CH3 ,0,@

6. Match the column I with column II and with column III.
[.8,6 i.,llii,.,l....,,Il,,.,io,ftirffirc *sl ,ru#tlr f

R-2-chloropentane Optically active di-chloro products (P)

". I -*-
I

opticatly active dichloro products (e)

il +-
R-2-chlorobutane Optically active di-chloroproducts (R)
i *, I -*-,
SumP+Q+Ris:
8" Match the colurnn I and II.

i,ii::iiii e..6f.ffia.ffion

Meso compound

Diastereomers

Optically inactive due to absence

of chiral center
 aff$, ft{ffiffir, Iii*i

9. Match the column :

l::i,:::.1,,1::,,i::: i:; : t:it:r :::r :t:::i': !ti:::r ': .: i ::t:i::i

Ecaffidn mt

(1) BD.:THF
.---.---------.-
(2) CH3CO2T

(1) BTg:THF
(2) CH3CO2D

CH"
l"
(1) BDs:rHF
I I (2) cH.co2H
,
\-/

(1) BH":THF
_------l------

(2) CH3CO2D

LO. How many distinct monochlorinated products, (including stereoisomers) may be obtained
when the alkane shown below is heated in the presence of Cl, ?

(a) 1 (b) 2 (c) 3 (d) + (e) 6

1.1.. How many distinct monochlorinated products, (including stereoisomers) may be obtained
when the alkane shown below is heated in the presence of Cl, ?

(a) 2 (b) + (c) s (d) 6 (e) B

ilf&si :,i,, ,,t.
.,,,.. ., ,.,,,,,,.1,.;.:,,',',,l,On .1 tmf*f,fyffii .,

12. Match the column :

dirnerization product

cHe -ct d,yho+

CHs -Cl + CH, -CHz -Ct d,y*;--)

CH, -Cl + CH, -CH2 -Cl

+CH, -CHz -CHz -CI d,y$;--+

H2C = CH-CH = CH -CH2 -Cl

+CH, -CHz -Ct -;;ft;--+

QHs

13. HtCl :
I

I -P--,
tr, '-' (x)
(x). total number of di-chloro product
cH2-cH2-cH2-cH3
S-2-chloro hexane
 i,{ffi

L. A-a;B-c;C-b i

2. A-b; B-c; C -a; D-c; E-c; F-b; G-c

3. a,b,c
4.a
5.c
6. a-q-x; b- s - z;c- p-w; d- q-x
7. P + Q * R: 10
8. u-q;b-ptc-r;d-s
9. a-p;b-s;c-q;d-r
L0. a
11. e
12. a-s;b-r;c-p;d-q
13. 9
 re

HYDR0GARB0NS {ALKENES}

L. (R)-3-bromocyclopentene (shon'n beiou-) reacts with BrrlCClo to form rwo products, Y and
Z,Y is not optically active (does nor rorare plane-polarized light). What is the structure of Y ?

)-' LL-. 17
7

Brs
urBf A,,urBr
o""'u. (e)R,
(a) (b)
rq" (c) -..('
-!-L
tsr -Br
(d)
Bi"

ffi
2.A 2HCI
----------------) / -cl Reactant (A) can be:

(a)

(c)
,$ (d) All of these
rr'rce I9,.t
-4,9ffi,nH., >; Major product
,,,,.'.,

B. of the reaction is :

k
r"rft o)O< ,.,ef
I
(d)
er CI
I

4. Of- -**
Which of the following products cannot be obtained in ozonolysis of o-xylene?
oo
(a) CHO
(b) cH3
ilil
I

CHO -c-c-H
oo
ilil oo
ilil
(c) CH, (d)CH3
-C-C-CH3 -C-C-CFIO

s. o ---E---- Major product of the reaction is :

E
OH

@ (b 100
I

re
(a)

(c) (d)
OH

cH,- co2K
-
6. I - electrolvsis
, 14y (Kolbe electrolysis method)
cH, co2K (major)
-
Product (A) of the reaction is :

(a) CH, CHs (b) CH2 : CHz

(c) CH, - CH : CHz (d) none of these
-
o' , a ,g t^ , (C); product (C) of the reaction is :
Zn LiAlHo
=',:4T!
Or a

o
,rn
OH
(a)
A (b)
A (d)lft
 8' I4l' Product I4l is :

, -#;-
Br
Crl
Br
, ,or on

(d)
,o
c)<_,. Br
H

9. The reaction of propene with HrO" will proceed with which of the following intermediates ?

o oH, OH
I o!
(a) CH, (b) cH3
-CHz-CHz
o
-cH-cH'
oH, OH
I I

(c) CU, CH, (d) cH3

-CH - -cFI -CH=
LO. Which of the following bromides is the major product of the reaction shown below, assuming
that there are no carbocation rearrangement ?

eo
(/ +
,, "HP5",,,)-)
c"H"Br

(a) (b) (c) (d)

11. Which of the following reactions results in the formation of a pair of diastereomers ?

(a) HBr, (b) HBr

5#.,
H"C H 1. BH1, THF
(c)
ixztuH" (d)
,,,lp" oH ,
-rr" '

,
12. What is a likely product of the reaction shown ?

,,,,d,^=
BrzzcHaoH ,
I ll
\,/
 "&::,
H"C

(a)
"$;ha.,, (c) *r.
13.

14.
(a)
r
Whi ch of the fo llowing, when undergoing addition of HBr, wili
dias tereomers ?

(b) (c)

How many transition states and intermediates will be formed during the course of following
reaction ?

H"o. H*

(a) 3 uansition states and 3 intermediates (b) + transition states and 3 intermediates
(c) 3 rransition states and 2 intermediates (d) 5 transition states and 4 intermediates
15. Product of rvhich of the following reactions, is racemic mixture ?

CHs

(b)
CH:

(c)
#
cHs
_-j_)
H,
Pd

L6. The product(s) of the following reaction can best be described as :

H!r,
(a) a racemic mixture
& (b) a single enantiomer
(c) a pair of diasteriomers (d) an achiral molecule
17. Taking into account the stability of various carbocations and, as well as the rules governing
mechanisms of carbocation rearrangements, which reaction is most likely to occur during
the given reaction ?

MHG->?
 Br
(a)
>t_ *
(b)b
Q
(c)b
18'
(d) None ol'
Consider the following reaction in which the intermediate carbocation loses H+ to give
the
final product ?

H+
.-\Z ,,^/
which of the following energy profiles best represents the overall reaction
-+ ?

(a)

19' Methyl vinyl .&qt:-t{r(

- cfl -.o.SHr, areacrs with Brr/cHroH. If methanol is reacting as
water would, and if this reacrion-follorvs rypical mechiirism'of .f..trolt11i. uaai,iorr, ;i;i
would be the expected product ?
-'

(a) "-<".:: ,., <3::: (d)"t-zo

\o.r,
"ri'>-"t'",is
20' 2,4-hexagiyl. (C6H6) allowed to react with Li in NHr(liq). The product obtained is
treated with equivalent of C12 in CCl4 . Which of the followin[ constirutional
-1 isomers are
possible products ?
cl
-,t.--\- ;\*
d,J,.,cr 4
cl cl
X.J'a"A-
cl cl cl

(D 0r) (rr) (IV) CV)

(a) I and II O) II and III
(c) I and V (d) I and III
2]^' Which of the following
is the best stereochemical representation when reaction berween
l-methylcyclohexene and NBS react in aqueous dimethyl sulfoxide ?

(")q (b)e*" ,.,d;. (d) None of these

Br
 . lr" ,.' ':ijr.'.,r: :ij'i:

22. Which of the following is among the major products of thet--^-.

reaction of
rea(
(E)-3-methyl-2-pentene with BH, in THF folowed by the^addition of H rO 2lao'z

Et HMe(b) H
(c)
Me OH
(d)
H H
(a)
H MeH Me H Me Et OH
Me Et Et
23. Compare rate of dehydration of (i), (ii) and (iii) by conc. H2SO1.
OH

(i)

(a) (i) > (iii) > (ii) (b) (i) > (ii) > (iii)
(c) (ii) > (i) > (iii) (d) (ii) > (iii) > (i)
24. How many products will be formed in this reaction ?

1. OsO.,
2. \aHSO3

(a) 10 (b) z
(c) 3 --) (d) 4
H\ /"H
25. /c
_r--
-L-
t ta,an3)2cH2oH --B'r---e 1a) Product (A) of the reaction is:
cHs
Br Br

,,,.;)p<!xl
Br

(c)'i>g!;, (d) x/-\Lo x- Br

cHs
I

26. CH"-CH+HrC:
"l' CHz -#C*(A); (A) is:

+\
CH:

(a) o)
>E<:
(d) cH3 jn -cHz - cH : cHz
,>:<
(c)
cHs
27. Predict the product (A) of the following reaction

A+A
,rrG ",e( ,oe( (oo(
--
-z...-..-...-..zOH
( I H--, (A) is:
28. (A) Major-product
a

,,,en G)f
(Major)
\,/

,.,eX- G)u
29. Di-imide (NzH+ ) is used to reduce double bond of:
(a)
-9: o (b)
-C N
: (c) (d) : CH
I -No, -CH -
30. n'' ,(A)-1ffi.----.!ft \azcrzs ,161
O
End product of the reaction is :

o OH o

afro o)
A ,.rA (d)
A
31. m#ic*f"o
q
Product (A) is :

Br

&
Br

*,cr
Br

(a) (c) (d)

o+
.
82. o
H'(excess)
-{r
OWno<
' m Br

) +
e('":: l"::
Compound (A) is :
 oso+
X+
33.
d ' 72:
Y
1

Product (Xl rvill be :

OH OH

A,,,,rroH{u) Ao, tar(\I-o

t" (r.,rr,oH (.LsH (c)

2\a\H- H
- Pd CaCOr

Product (C) is

r"l
nj)c-.(X, ol oj)c-.<f c'l il)c: cHz (d) Ph-c:c-Ph

MMPP Magnesium mono peroxy phthalate.

-,(X) is
Product

(a)@ @
:

(b)

#
OH

r'ffi@ (d)

OH
OMe

* I

MCPBA
>
86. ,'r*rProduct (P) is:
%
o

,rffi
OMe OMe

(b)

o
 OMe

(c) (d) None of these

a,r0ar, .'
t.

sz. [T*..-o\ o,/: *1" , A;product (A) is :

\\4" ^{-\ Mannitor/water
/\'tl/
cvclic tt#fitr-a, complexed

(a)HoQ.r, .,y cHrJ&cH3

-
cHg oH oH bu

(c) (d)R",
o cHs
CH"
l"
38. + CBrCl, h' , (A) (no ring subsrirurion)
O
Product (A) is :
(a) Ph CHz Cl (b) Ph CHz Br
(c) Ph - CHz - CC13 (d) Ph
- CHz
- CBrCl2
- - - -
MCPBA
> (A) ; MCPBA --+ metachloroperbenzoic acid

Product (A) of the above reaction is :

(")oG c)Gl
t.rfi^|<ou (d)HofY
\-. . \,^
 \ 1.82H6

/at - H,o" Ho- !

'z
oH
(")!{o' G)}(oH (.)y\H (d))\
HO

4r. Which one of the following compounds gives acetone (CH3)2C

- O as one ofthe product of
its ozonolysis ?

42.
,rw G)w ,.,:.A,2
Addition of HCI to 3, 3-dimethyl-1-butene yields two products, one of which has a rearranged
(d)G
carbon skeleton. Among the following carbocations, select the possible intermediates in that
reaction ?

++
(cHs)3ccHCH2Cl (CHs)TCCHCH3 (cHs)2 qc(cH3)2 (cHs)2 ccH(cHs),
I

CI
l2 3 4
(a) r,2 (b) 1,3 (c) 1,4 (d) 2, 3
(e) 2,4
43. Conversion of cyclohexene to ryclohexanol can be conveniently achieved by :

(a) NaOH + H2O (b) Brz HzO

(c) hydroboration, oxidation -
(d) hydroboration hydrolysis
44. Trons-cyclohexane-1,2-diol can be obtained by the reaction of cyclohexene with :

(a) KMnOo (b) oso o

(c) peroxy formic acid /HrO* (d) SeOz
45. Bromination of (E)-2-butenedioic acid gives
(a) (2R, 3S)-2, 3-dibromosuccinic acid
(b) (2R, 3R)-2, 3-dibromosuccinic acid
(c) a mixture of (2R, 3R) and (2S, 3S)-2, 3-dibromosuccinic acid
(d) (2S, 3S)-2, 3-dibromosuccinic acid
46. The major product formed during the reaction of l-methyl ryclopentene with CH3CO3H is

(a)G: ,,,O4:X' (c)

ef;" O'*' ,0,
\-/ ,rrttOH

cH co2H
47. ll - NaoH
, (A) (B); Product (B) of the reaction is
CH CO2H (twomole) -jl'u@--+ :

-
(a) CH, CHs (b) H2C CHZ
-
(c) H-C:C-H (d) CH2
-:
CH CH CH,
- -
 o-H
48. -xrr-= (ractone)
O cyclic ester
(Bromolactonization)

,rrro+o (b)
r+,
Br

qg"
Br
I

(c)-" (d)
Br -ozH

49. Product (P) is:

O
Cyclohexene
,,[f],,

(,)eJ- *,eJ-ocH2cH',r(: ,.re(:::

50. what is the major product expected from the following reaction ?

KI\InOo

-_-----)
HO- cold

(d)4"
OH
H
(c)
OH

5L. CH, -CH : CH. - .=r.1.------- 6a; ' Product (A) of the reaction is :

(a) cH3 {H O) HrC:CH-CHr-Br

-CH: - Br
I

Br
(c) CH3 :CH: (d) Br CH, CHz Br
-Q
I
-CH, - - -
Br
o o
il il
Et_CH_C.-- Et-CH-C---
s2. t9- cH'
cH2
.-1 I
CH2- CH/ ^--? ;' rLLq
Reagenr (A) in the reaction is :

c:o
I I

C:CHz
cHr/ cHs'
(a) o r lZn(HrO) (b) HIo4 (c) CrO, (d) Coid dil. KMnOo
 .l*-i*-tnl,itii,iffl|.i
'r
l oso'
53. , Product of the reaction is:
tar, 2. \aHSO3

9Hg CH" -oH

OH .71.
( \<oH
OLJ, (oex;.,,
=
l,rttCHr
CH:
(b) \_,toH c.r r__c<CHl

=
: =cHs
cHs OFI

54. \\-hich Corlrpourd is a possible product from addition of Br, to 1-butene ?

ra)Bru Br'
b)Brn Br

(c) srA'.ryB' (d)B'i^

Br
b5. Addrtron of Br, to cu-2-butene w-ould give a product which is:
i .rJ ,lii'[1 ai (b) racemic
,'cj m.'sc (d) opticallY active
56. Aririiiion oi P-,r. ro runs Z-butene would give a product which is:
(a) achiral (b) racemic (c) meso (d) optically active
1o7, Addition of OsO. to cvclopentene would give a product which is:
(a) achiral (b) racemic (c) meso (d) optically active
58. Addition of BH. followed by HrO, to trans-2-butene would give a product which is:
(a) achirai (b) racemic (c) meso (d) optically active
CH3CHCH : cHz cH3cH - CHCH3

seo (a) Hro/H.

; Reagent A may be
(b) BH3.THF1 H2O2 -OH-
:

(c) HS(OCOCH3 )z.THF/NaBH4. NaOH (d) Atl are possible

60. The major product of the following reaction is :

cH: __ CH : CH, + HBr -(cuHtco)'o' ,

(a) CH, --'CHz Br O) CH3CH(Br)
-CHs
-CHz -
(c) BrCH,
-CH: CHz tal pn,
HO-.
HO'\R
t7u-/
61.
\-J -#-tal{5rrl
Identify (Bi :
2S ',, , OR6 ,Cftbm{$,W,for nr'JEE

'0' r'a
t" 'o'-a"o
no!{,.r,r)s__co2r,
(b) (7
,L{.
HoJ -icH2)r
-- co?H

zo'-/o
(c) (d) ,o-J\-L-1cH2)3
n -f{j-rr,z)q-co2H __ co'H

62. Which of the following is a major product of the reaction shown below?

U
-,-\z(j[].1 I}l
*------)
Lt al

(a) (b) ,.rfi::*

Br
63. In methr'l aicohoi solutioir, hrcimiire reacts with ethylene (etheneJ to yield BTCH2CH2OCH3
in addition to 1. l-dibromoerhaue because
(a) the methi-1 aicohol soi.,,ares the bromine
(b) the ion forme d inirii'r11r mal' rcacr ',virh llr or CHrOH
(c) this is a free radlcal reacriorr
(d) the reaction folloivs iiairovnltio\'s ruie
64. \rVhich of the follor,ving coirD.)Lin(i i',.rs the starting materiai for the oxrdation shown beiow ?

Ho
? ---.KM''o'' !." ,

(a)ll
\d ,orff
(c) (^>'^-<z
L_/
carff
65. Which series of reactions will achieve the tollowing transformatio n
Br

Fcr
I

,, I
C1
2 1 2
(a) Clr./CCl4 Br, (b) HBr cl. i,ccl r
(i) cl2/ccl4 NBSz'hv (d) NBS/hv cl, //ccl4
 (a)
D*
I N* q (b)
___>

I
?

d
I
I

67.
(c) (d)
e(
A triene is treated with ozone followed by zinc in acetic acid to give the following three
products. What is the structure of the triene ?

o o
Products : ,A, H
oo
A/\
(a)
(,
",^O
nre ,or@
68. Which of the following compound would yield trialkylborane shown below when treated
with BH3/THF ?

-\

(a) 2-methylbut-1-ene -(
(c) 3-methylbut-1-ene [3] 3x*;lill.?-il:
69. If the following compound is treated with Pd/C in excess of hydrogen gas, how many
stereoisomers of the product will be obtained ?

_a
 (a) 1
(c) 3
70. lVhich is the most precise designation of stereochemistry for the products formed in the
electrophilic addition of DBr to 1-methylryclohexene ? (D : 'H, an isotope of hydrogen)
Br

*,G*
Br

(c)G:', (d) both (a) and (b)

71. Consider the addition of HBr to 3,3-Dimethyl-1-butene shown below. What is the best
mechanistic explanation for the formation of the observed product ?
CH: H =CH,

cHs-C-CH: CH, -lr-+ H=c,,,rL

-Oat"
I

cHs HsC tsr

(a) Protonation of the alkene follorved bv a hvdride shift and addition of bromide to the
carbocation
(b) Double bond shift in the alkene following bi'the protonation and addition of bromide to
the carbocation
(c) Addition of bromide to the alkene follor+,ed b-v'- a double bond shifr and protonation
(d) Protonation of the alkene followed by a methyl shift and addition of bromide to the
carbocation
72. Propene CH3CH : CHz can be converted into 1-propanol by oxidation. Indicate rvhich sets
of reagents amongst the following is ideal to effect the above conversion ?
(a) KMnOo (alkaline) (b) Osmium tetroxide (OsO + /CH 2Cl2 )
(c) BzHo and alk. HzO, (d) o,lzn
73. Which is the most suitable reagent among the following distinguish compound (3) from the
others ?
(1)CH3C:C-CHs (2) CH3CH2 CH2 CH3
(3) CH3CH2C (4) CH3CH : - CHz -
(a)
- CH (b) Bromine in acetic acid solution
Bromine in carbon tetrachloride
(c) Alk. KMnOo (d) Ammonical silver nitrate
74. The principal organic product formed in the reaction given below is :
CH, : CH(CH2)8COOH + HBr P"'o*id" ,....
(a) CH, CHBr(CH2 )8COOH (b) CH2 : CH(CHz)eCOBr
-
(c) CHTBTCH, (CHz ) sCOOH (d) CH2 : CH(CH2 ), CHBTCOOH
75. When 2-butyne is treated with Pd - BaSOo; the product formed will be :
(a) cu-2-butene (b) rraru-2-butene (c) l-butene (d) 2-hydroxy butane
:
76. In the reaction. CH.C C
-CH3 'I-v -f -q-CHr.Xis :
-= *---rCH, '

56
(a) HNO3 (b) O z (c) Og (d) KMnOo
77. Which of the following alkene on catalytic hydrogenation given cis and trons-isomer ?

(a) Hzc#.r, (b) rr.S.r,

A
CH

(c).r:fi (d) all of these

cHs
78. In the reaction of hydrogen bromide with an alkene (in the absence of peroxides), the first
step of the reaction is the ......... to the alkene.
(a) fast addition of an electrophilic (b) slow addition of an electrophile
(c) fast addition of a nucleophilic (d) slow addition of a nucleophile
79. Which of the following alcohols cannot be prepared from hydration of an alkene ?

rut*H rurTou
r.rLoH (d) X,/oH
80. of
Which the species shown below is the most stable form of the intermediate in the
electrophilic addition of Cl, in water to cyclohexene to form a halohydrin ?
H

(a)
\9,/

^Sa,
I ,rrG.,
H
H

(d)O.,
H

81. The reaction, (CHr)2C: CH, + Br'-----+ (CHs)rC -CHrBr

is an example of a/an . step in a radical chain reaction.
(a) initiation (b) termination
(c) propagation (d) heterolytic cleavage
 Which of the following most accurately describes the first step in the reaction of hydrogen
chloride with l-butene ?

@ fr#./--+r^r^.+cl'
o) n b./--- .:\/ +cl-
(c)
EISN+ +*
(d)n Cb,/---r.,A,n*r-
Which of the following best describes the flow of electrons in the acid-catalyzed dimerization
of (CH3 )2C =CH2 ?

th
(a)
/ti
HsC CHg
HzC : ca/cH'
CHs
(b)Hgc>r.>
Hgc
G.a" cHs
Hzc\
H2c a c!
lHs
Hgc
l\.,,
r ( '.,, \
(c)
"tr\\-.
,C:
CHZ
(d) Hzc
- !f"'
cHs
Hsc
84. Hydroboration of 1-methylcyclopentene us ing 82D6, followed by tr eatment with alkaline
hydrogen peroxide, gives
Me Me Me Me

,ftrrilD ff,,rrlD
,, q,rrroH qru! H ,rq:::::' ,.rq:::::'
H cooH ", OHH D
Bs. H +ht HooccH(Br) cH (Br) cooH
HOOC
(P) (a
,-.
HOOC
(a)
COOH
+fu HooccH(Br) cH (Br) cooH
(n
The correct statements with respect to the above pair of reactions are that
(I) the reactions are stereospecific
(ID G) is erythro and (Y) is threoisomer
(IID (D is threo and (Y) is erythro isomer
(M each of (P) and (Q) gives a mixture of (D and (Y)
(a) I and II (b) I and III (c) I and IV (d) II and IV
rn{DRocAR,BONS {ALKENES) 0$,fi

86. The products P and Q in the following sequence of reactir-rns. are

MeO
r1: ') I le'-*
Li. EIOH n .

\Hrl1) ti:,--i i l.l-l'.1:'> x

Me

-t-

MeO \1eO MeO

CHO Me02C
(c) (d)
COMe OFIC
.\ 1e 'Me
87. 4-Pentenoic acid rr-hen treated lvith 12 and NaFICO, gives :
(a) 4, S-diiodopenranoic acid (b) 5-iodomethyl-dihydrofuran-2-one
(c) 5-iodo-tetrahr dropl.ran-2-one (d) 4-pentenolyiodide

HrSOr.0'C /
88. tA) -_Hcf-+
(B); Product (ts) of the reaction is:

: CHz

(i) alc.l(OH
/n\
_-> r/1\li) NaNl{, (n\
n--_ r-- ^r (C) .
89. - f;--' ral (ii) NaNr{,| tJ ) -f;ff;::*;'(Cl ' Froduct is :
(Sqrrene)
(a) Ph -* : C CNa (b) Ph._cI{2 _-c: ctrJ
(c) Ph ---C : Ph"-CH: C :=CHz
./ t'\
C -_CH-1 l.u,
90. Which of the following will give a mixture cf cls and trons-1,4-dimethyl cyclohexane, when
undergo catalytic hydrogenation ?

(a) (b,+ (c) (d) both (a) & (b)

Ln3 C,is_3-6 dimr:thyl

cyclohexene
91-, An optically active compound A with molecular formula CsHla undergoes catalytic
hydrogenation to give meso compound, the structure of (A) is :

CH
.cH, - cHg
,"r# (b) r I ,'rft.',
-,{' (d)n
\_/
/z

cH=& CH:
CH:
 CHs CHz\ 7CH; CH3
- C-
92. - -C:
* HBr R"o" -+ Products
CHs CHs ie"iio*ia"l
How many products will be formed in above reaction ?

(a) 2 (b) +
(c) 3 (d) 6
cHs \ //D
93. : C-.
D-C CHg
-+-- Product of the reacion is :

(a) Racemic (b) Diastereomers

(c) Meso (d) Pure enantiomers

94. cis-2-bute""
-ffi*, product ; Product of the reaction is :

(a) Racemic (b) Diastereomer

(c) Meso (d) E andZ isomer

95.

Rate of reaction towards reduction using (H2lPt) :

(a) a>b (b)a:b

(c) b>a (d) Reduction of given molecule is not possible
oo
s6. :>f"i<Xom ProductA + cH3
-X-.r,
Product A of the above reaction is :

o
il
(a) R-C-R (b) R',- cHo
(c) R CO2H (d) tjoth (a) and (b)
-

a|c -o-o-H
cHr.. V (MCPBA)

,cH, ),

H/ \H cH2cl2

MCPBA -----) Metachloroperbenzoic acid

 (a)
t");r.<L, (b)
H,
H- ,CHS

Y -t',
r.d)
CH:
9H,

eB. ',A''H
I_J tffi#_, (A) ; Product of rhe reaction is :

cH, cH..
I "n
CH"
l"oH IH

GI
J

(b) (c,@ (d)d)

ucHs
gg. CHs
- CH
- cu,' -9$j}_-+
(2)CH3CO2T
@) ; Product (A) of the above reacion is:
(a) CH3 CHD CH2D (b) CH3 CHT CH2T
(c) CH3 - CHD-CH2T
- (d) CHg - -
- -CHT-CH2D
1OO. Optically active isomer (A) of
(C sHecl) on treatment with one mole of H2 gives an optically
inactive compound (B) compound (A) will be :
(a) CH3 CH : CHz G) CI-CH : CH CHe
rl
-CH -
cHf I cHs
-CH -

(c) CH3 : CHz (d) CHs CH-CH : CHz

-CH -CHz -CH -CHz-
&
I

C1
1-0L. An organic compoundCaH6 on ozonolysis give HCHO, COz, CH3CHO. Compound will be :

(a) H2C: CH-CH:CHz G) CH3 C : CHz

-CH:
(c) cH3
-c
: c
-cH3
(d)l-l
uctt-o.,-H*
LOz. , major product of this reaction is :
Hzo

,,,QfJ .', (')qHz-oH ca,ofo,

OH
I I OH
103. CH3-CH KMnOa- ) (A)-{i(B) -;ffi+(cl
I

cHs
Product (C) in the above reactions is :
 H cHe
I

(a) CHs C-Br (b) CHg

I

C-Br
- -
I
I
cHs cHs
cHs
(c) CHs (d) CH3
I

CH
-CH-H I
-
CH2-Br I

CH2 - Br
cHa

tO4. CHs C
I

: CHz + (CH, )2CHCH3 (A)

- -r#-C8H18
Unknown (A) in the above reaction is :

(a) 2,2, 3-trimethyl pentane (b) 2, 2, 4-timethyl pentane

(c) 2, 2-dimethyi hexane (d) n-octane
OH
los. HBr + (n) ; Product (Q) is
Ar,-j2- -Ueo\ 1O, :

o
(a) (b) Br il:oMe
cHrot-lo2cl t,,
o
o
(c) cHs -l -oMe (d)
,rkoMe
106. ta 4* , (A) !!rd4il. , 6tr; cos > (c)
\.AOH a KMnoa

Product (C) of the reaction is:

(a) (b)G" ,.,Q(' @)fto

\, cHo
lO7. What is the major product expected from the following reaction

1n LcH.
?

D -cl > product

,rr,q:' .',q:' (c,q, (d,q,,

H H CI H
 cHr-cH3

G
_cH2-cH3

(b) L
,A.LoH
(c)
f>io,
(d) L
_, ls,,r, ., 1,,,,,,
H Br

BH3/rHF
ro9. ff'n' 1'
2'H2o2/oH
> A: Product A is:
\r/

(a)ef,,{' (b)(X: (.)O;X' ,o,a--6;X'

\.^*iilon
OH

1ro.
ef"'
(a) (d,q_,
111. Choose the correct product of the following reactions :

o
ooH

OH

(a) (o)ef'f,"'
=
cHs
l!2. How many stereoisomeric tetrabromides will be formed in the following reaction ?

/\/ "',
ccl4
,

(a) 2 (b) 3 (c) 4 (d) 6

I
 oisomeric pentabromides will be formed in the following reaction ?
Br
I 2Br2
./\/
-*-
(a) 2 (b)a
(c) 4 (d) None of these
tt4. ./\Z-EH6- {a) -Jff--+ (z) (major)
Identify (Z) in the above sequence of reactions :
(a) ./\Z (b) ,'^/
CH,
(c) (oU (d) ,A.l-6"g1

cHs
lls. -cH-co,K
,
' electrolvsis
,(A)(Major)
cHg
-cH-co,K
Major product (.{) of the above reaction :

(a) ./\.2 (b) [T-n

(c) ,,^,/ (d)
ooo
L16. \ .H-.nri% /\,/\
r.{ I

(only one enantiomer is taken)

'vVhich of the following statement is correct about A and B ?

(a) A and B are mixture of diastereomers

(b) A and B are mixture of enantiomers
(c) A and B are optically active
(d) B is racemic mixture

A
CH"

aas ^,,
1,1,7. A/
cH3o NaBH+
,A o, >B Hro ,(c) (one of the product)
o

' ,ft',"
Identify the product (C):
 oo cH2
I - oH

- C- C-
(a) CH3 (b) cH
I

O CHs oH
- -
CH, OH
-
CHO CHO
I

(c) CH OH (d) cHoH

- I

CH, OH CHO
-
1r8. q:: ,o' , 1y; cHz=cr1:?Ph"g.o
, ,,

Product (Y) of the above reaction is :

(,)oJ
(c) (d)q::"-cHz-oH
ffi:cH-cHg
1r.9. Inthe reaction Me Na'uliq'NHs, p
- c - c-Et 't "',(O
ccl4 ; then eis :

(a) A pure compound which is optically inactive due to internal compensarion

(b) A binary mixture which is optically inactive due to external compensation
(c) A binary mixture which is optically active
(d) a pure compound which is optically inactive due to absence of chiral cenrre

!2(J.

Which (rc-bond) will reduce first, when above compound undergoes catalytic hydrogenation ?
(a) o (b) b (c) c (d) d
1'2l. Compound A, which is a degradation product of the antibiotic vermiculine has following strucflrre

OO
ll
- c\o.r,
il

.r/c-' ,ry''ntrrl"'' 1," - cH

o
(cH3)2s
< *dh-"51L, ' unknown (c) is:
o,!f]"- -#-,o,H]*
 cq!-
o) cn(c'.r/tn'\./cH:
'll o - cH3
cHz
tn' tn'-.rr t'^ ?
rol rn{t :.r/t'^.r/ rr{'-ocH,
il
cHz
CH" o
ll' il

(c) cnrlc-' rn{"^.n/ "n :.r/t -o.r,

\r"
cHg
(d) None of these

A B
122. ----+
-)
{
Reagent (A) and (B) in above reacrion are :

(a) A=RCO3H,B:HzOz (b)a:RCOsH,B:HIO+

(c) A:RCO3I{,8:Os (d)A:Oe,B:RCO3H
12i3. Rank the following in the increasing order of rate of reaction with HBr .

(P)
"5 (ob (R)
>1
HNij)
(a)R>P>Q G)A>Q>P
(c) P>R>S (d)P>S>R
124. Select the reaction(s) that rvould result in rhe formarion of 2-bromopropane.
(I) CH3CH : CH2 - HBr Peronde , (II) CH3CH CH2 + HBr cclo
- >

(lII) CH3CH2CH3 - Brz :'' ) (IV) CH3CH CH2 + Br, --S9L-

(a) I and III
-
(b) II and III
(c) I, II, and III (d) I, II and III
125. Which of the following reactions generates the major product ? Ignore stereoisomerism.

(a)
e)-+ HBr--.+ e(.
 ' I, rj..
. .i :':: -:: .
.; i -.t::.
I!ri:i.,
:trt:iii:
..i .
r,:,i:.. : , ..' :

*,e)' (1) Hg(OAc)2, HzO,

@\Ao,
THF . a1

,,e)' (i) BH3

(2) OH-. H:02. H2O
er"'
(d)O' H:o. H:so4
) fton
\,/

L26,
(e)
o' -+uk::
In the gl'en selecur-e hr-drogenarion rt'hich combination is incorrect ?

(a)
-#:Q (W.C. - Wilkinsons catalyst)

(b) -fi_' + (w.c.:wilkinsonscatalyst)

(.)fu -#,fu
,o, /-*-* cHz
-cH:cH-cH3

127.
lrlPo Na/NH3(t)
(B) *cPBo r (c).

Compound (C) in above sequence of reaction is :

H H
(b)

o
(d)O cHz-[-O
 HBr
128. , @):
R2O2/lw
cHg

Major product (A) is :

,rr@L, *,GL
,rffi r.,d:1-
Br

129. In the reaction given below, the product would be :

: ?,
CHs CH CH CH, CH2
- - -Ed--CHs - -CH -CHs
(a) a mixture of diastereomers (b) optically active
(c) optically pure enantiomer (d) a racemic mixture
130. Surprisingly, the reaction show'n below goes through classical carbocation. What is the major
product of this ..uT,:n ,

+HBr-.......+
O
(a) trans-1,3-dibromocyclohexane r'b) cu-1. 3-dibromoo-clohexane
(c) trans-1,2-dibromocyclohexane (d) cu-1. 2 -dibromoc\-clohexane
L31. The major product of the reaction given belort' is :

//\/oH --B'=---2
OH OH
(i) Brrr,,,r)_.__,OH (ii) e. oH
Br Er
,rrD r1e,,,,A^-O, (i') Ho i
*, -, -, oH
H /\ CH"Br
(v) - .-,/"\iH
(V'JLJ
CtsCH2Br
(a) ,(i) and (ii) (b) (iii) and (iv)
(c) (v) and (vi) (d) none of these
 i

1.32. Which reaction will occur at the fastest rate ?

r"'o 'u" h)a( HBr*

(c)o ,rr, d' @a( n", ^(r,

C1

L33.
o Na
dry ether

Above reaction is known as :

(a) Wurtz reaction (b) Wurtz fittig reaction
(c) Fittig reaction (d) Kolbe electrolysis
o
ti
lg4. cH3
Red P -HI , o
-cHr-t-,
Product A is :
(a) propane (b) propanoi (c) prapanoic acid (d) propene
135. Which of the following compound give diastereomers when treated with Br2 in CCl4?

(b) (d)

R.
(a) (c)

cHs
Methylcyclopentane 1-Methylcyclopentene 3-Methylcyciopentene 4-Methylcyclopentene

136, A mixture of C zH6, CzH+ and C2H2 is bubbled through alkaline solution of copper (I)
chloride, contained in Woulfs bottle. The gas coming out is :
(a) original mixture (b) c2H6
(c) C2H6 and CzH+ mixture (d) CrHo and CzHz
Brzf ccr+
tBT. ry OH +- Possible products ,(y) products
(x)
The number of possible products for x and y is :

(a) 2,4 (b) 3, 5

(c) 3, 6 (d) 3,4
138. Select the incorrect statement :

(a) Bromine is more selective and less reactive

(b) Chlorine is less selective and more reactive
(c) Benzyl free radical is more stable than 2" free radical
(d) Vinyl free radical more stable than allyl free radical
139. Which of the following compound does not evolve CO2 gas, when undergo oxidative
ozonolysis ?

JI
a\
(a)l
t.,\./ I (b)
o^
(c) HzC : CH
- CH : CHz
14O. cu-3-hexerr" (o) > meso 3,4-hexanediol
(d)
o
rrcru-3-hexene (b) ) meso 3,4-hexanediol.
Choose pair of reagent (q,b) for above conversions.
(a) Cold KMnOo,OsOa (b) Cold KMnO4, RCO=H/urOo
(c) RCO tHlH3O€, cold KMnOa (d) None of these

l4t. -11#*-(A) += 161 PhsP:cHz(2mole)',t,

Product (C) of the above reacrion is :

(a) 1,3-hexadiene ib) 1,4-pentadiene

(c) l,3-butadiene (d) 1,3-heptadiene
142. How many carbon-hydrogen bond orbitals are available for overlap with the vacant p-orbital
in ethyl carbocation ?
(a) o (b) 3 (c) s (d) 6

1 43.
o
To achieve above conversion, the reagents used will be :

(a) Os lHzO r, HO- f t (b) HBr, alc. KOH, O3, LiAIH o,H* lL
(c) HBr, t-BuOK, O3, KMnO4, A (d) HCl, KMnOa(cold), g* lt

144. (major); product (X) is:

-ffi--rX
 (a)
AA
\-o^.
HgoAc
G)
\-HgoAc
oAc
(c)
A
C^-",
(d)
A
\,^
o

OH

L45. Decreasing order of heat evolved upon catalytic hydrogenation of given reactants with a Hz
(PdlC) is :

(a) b>c>a>d
! GUG (o) (b)
(b)d>a>c>b
(c)
I

(d)
(c)d>c>a>b (d)c>b>c>d

146. )-.-
(a)
A-= (b)
A,,^_ >a/
(c) (d)

The correct order of heat of hydrogenation of given molecules is :

(a)d>c>a>b O)d>c>b>a
(c) b>a>c>d (d)d>c>c>b
1. Hg(OAc)2
147. OH A
2. NaBHa
Product (A) of the above reaction is

,,\)a ",(r
:

fl,
(c,

Q "rff
I

148. fTf,:f,ii,
I I +HBr +A
(Major)
Product (A) is :

,", Ij" ,0,{j" ,rd"

l4g. Product; comment upon optical activiry of the product.
-ffi}
(a) Racemic mixture
(b) Diastereomers
(c) Meso
(d) Optically inactive due to absence of chiral center
CHs

l5O. Hg(oAc)z/EtoH
I

CHs
-
C CHs , 141
-CH - eo%)
Product (A) of the above reaction is :

CH" CH"
l"
(a) CHg-C
l"
(b) cHs-f
1H-CH3 -tH - cH3
HgOAcOEt OEt HgOAc

CH" CH"
l-
(c) cHs-f (d) cHg-f
l"
-tH cH-cH3
OH HgOAc
-cH3 -
HgOAcOH
r sr. Me2cH - nau
-ffiCal ffifr+Cal
fH-
OH
Product (B) of above reaction :

(a) Me2C(OH)CHzMe (b) Me2CH CH- Me

- I

OH
(c) Me CH- CMe3 (d) HO CHz (CH2)Me
- I
- -
OH
152. In which of the following reaction, Markownikoffs rule is violated ?

(a) CHs (b)

\-/ CH,
-O-CH:CUr*---+
' CCll ---r -NH-CH:CHz-g-CCl4 7
(c) cHs-s-cH-cI' rz-crrryl
HBr
(d) o2N-cH :cHr-H>
153. Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is :
CH : CH. CH: CH: CH:
l'
CHz CHz CHz

qNoz
(a)
 (a)a>b>c>d (b)b>c>a>d
(c)d>b>c>a (d)b>d>c>ct
154. 2cH3 -c :cH, E@I- (A)
(major)
ln
Product (A) is :

,rrm:: "'on
(c)
cHs

15s. -+-- (A)-H-+,if,I,

7cH2-oH
Product (B) of the above reaction is :

,.,ero* ,o,(}o*

(.)e)' (d)ao-oR
156. Which of the following compounds gives the same carbocation on ionization ?

-rU-r "
3 4
(a) 1 and 3 (b) 2 and 4
(c) 1 and 2 (d) 1 and 4
!57. For the following reactions the major products are shown :

: CH-CH-CH3j 2SSCH2CH
H2C : CH : CH2 :CHCH,
-CH -++--rH2C
lt-
Br Br

These provide an example of .1 control at low temperature and, 2 control at

higher temperature.
72 t2
(a) kinetic thermodynamic (b) thermodynamic kinetic
(c) kinetic kinetic (d) thermodynamic thermodynamic
a

L58. What is the product of L,4-addition in the reaction shown below ?

HCI

@),)4(cl rD4ct
-.€

(.)r-cr rar0*
,se.'T>o4.
Dehydration of the above compound will give :

(a) meso product (b) racemic mixture

(c) diastereomer (d) optically pure enantiomer
cHz - cH3
I

160. H-tCl
I

I --g--+
ccto
CH = CHz

What is stereochemistry of product ?

(a) Racemic mixture (b) Optically inactive
(c) Diastereomers (d) Meso product
\g11 ,A Ho >
1.61.. - ",, " -
cafo/
End product formed in the above reaction is :

(a) Optically active (b) Racemic (c) Meso (d) Diastereomer

162. How many moles of BH, are needed to react completely with 2 mole of l-pentene in
hydroboration-oxidation reaction ?
(a) 2 mole (b) 3 mole
(c) 2/3 mole (d) 312 mole
ocH3
H'o*
168.01- -fuA >B

Product (B) in the above reaction is :

oo OH

,.,qocH3 (d) 6
Y
OH OCH
 [rc] r'{
14
164. H2c' -cH -cH, -*ffi#-(zl
Product of the above reaction is :
74 t4
(a) HrC : CH (b) H2C:CH-CHz-Br
-CHz -Br
74
(c) 9H, (d) both (a) and (b)
tl {HBr -cH3
Br
16s. In which of the following reactions 1,3-butadiene will be obtained as a major product ?

(a) Br
-CH, -CHz -CHz -CHz -
Brffi
H'so+ ,
oH conc'
(b) Ho cH z
- cHz-
cHz cHz
- -
j*,,F -
(c) H2C: CH-C : C"
(d) All of these

166. H2c__. ra"t

"\cH: ,!'i=
2o'c
,- *2'ca(oH)i I , A; IdentifvA.
A

CHr

(a) CH:-Q-FHz
l" o) cHr-9H -CHO
\o/ CH:
o cHg
ll
(c) CH, (d) CH3 :CHz
-C-CH2 -CH3 -C

167. *o'

Product (A) is

,"r$
:

",oy
.,Q I
 CH,{A NBS
168. ,[|- J+A(major)
nXrr,
Bromination take place at :

(a) o (b) b (c) c (d) d

L69. Which is incorrect statement about heats of combustion ?

r
(a) rulF{'}{,G
(c) Iso-butene > frans-2-butene > 1-butene (d) n-Hexane < n-Heptane < n-Octane
l7O. Predict the major product of the reaction.
cHs

CHs
I
.,,,@.-["", (Froduct)
-C:C-CHz-CH:CHz
I
H+
cHs
CH: CHS CH: CHS
tt
(a)cHs-c- lt
c-
c -cHz-.{ln, (b) cH3
- \o- c -cHz -cH :cHz
cHs cHs cH 3 cH3

(c) CHs-C
tt C (d) CH3
tt
- -CHz-fH-CH2 -C-C-CHz-CH:CHz
OHOH I L
OH OH

1.7r. cord d,. Kllnoo product

, of the reaction is:
@
(a) Meso compound (b) Enantiomeric pair
(c) Diastereomers (d) Optically pure enantiomer
OHHHH
HO-C il
Y ..H V ..H V V ..H
\H
rzz. cH3o.\--t\"-t-a
i"t:li ",' ^)l' r:c/t\r ,)?'
^'/'-
HHHHH
I o' ia,.i,toromethane)
J r CH3)rS

(A) + (B)
Opticall-v* acive Oprically inactive
..1',.i.tij,l,.t:. :l:i:,,.., ,llij,i:r,'l,ti ...,::.r.... .. ,1. . .. . ' ,,ii , '
.
rrmBOC fiEgltfiS,lfr*[I@lEf,
.

;",:,,1,,,

Product (A) of above reaction is:

(a) CHsoAn -CH z -CHz - CHo
co2H co jH
(b) cH3o
- cH:-cH -CHz - co2H
(c) CH3O CHz CO2H
-CH -CH: - -
co2H
(d) cH30{H -cH z-cHz-cHz -cHo
co2H

Hz (2-3atm)(1 rnole)
173. , Products ; comment up on optical activity of products.
7Oo/oPdlC

(a) Diastereomers (b) Racemic mixture (c) Meso (d) Optically pure enantiomer
o
174.

W'
Addition of a mineral acid to an olefin bond ieads to major product, Identify it:

w
(a) (b)

(o Br

,.rO
\r (d)

aBr
I

t7s. Ory.# product

A
In polyenes that contain differently substituted (C={) double bonds, it is possible to

,"Q ,"Q ,.,-

hydrogenate chemeselectively one (C:{) double bond. Product is :

X "'+
 MCPBA
176. > Product
l|__",
(MCPBA ----+ meta-chloro perbenzoic acid)
Stereochemistry of the product of above reaction is :

(a) Meso (b) Racemic

(c) Diastereomers
(d) Optically inactive due to absence of chiral center.

177.

Identify product (P).

'^'{ "'$ "'R" "'t

17g.

A isomerise to B on addition of traces of acid Hfo+. compound (B) is :

OH

SOCI,
179.
pndi=E? A

Product (A) of the reaction is :

 (c) (d) None of these

180. HO i %A). Producr (A) is:

^

.,4 *,-A-- ,.,O @)4fr

18L. Which of the following reactions do not represent the major product of given Birdt reductions ?
(i)-@raT,*'+(ii)OrafuO
CO?H QozH
l-
,,,,6E*?6 ,*,[O]#il d
(vii) 2-bu.^. crs-2-butene
- *k;*
(a) (i), (iii), (vi) (b) (iv), (vi), (vii)
(c) (iv), (v), (vi) (d) (i), (ii), (v), (vii)

182. sHs
) Hzoz,HC
>(A)

90
OR
Product (A) is:
 !itin!:rii+

OH

Hint
oH(c) oH (d)

m
OR OH
: Think carefully about the relative stabilization of developing positive charge, when the double bond reacts
with an electrophile.

183. Hocr >(A)-q3'rtil

25'C

Correct statement about above reaction is:

(a) A = cis-2-chlorocyclohexanol, B = cyclohexeneoxide
O) A =ffans-2-chloro c,vclohexanol, B = anti-diol
(c) A =trons-2-chlorocvclohexanol, B = cyclohexeneoxide
(d) A = cis-2-chioroo'clohexanol, B = anti-diol

184. H= , Predicr the major product:

(a)rP
---A H'soo
18s. II il ,(Maior)
(A) ; Product (A) is :

,rr4 o,)o ?,

G*",,-
82Br

q
196. , Major product of the reacdon is
-- cc}4

(a) Bd2
Bd2
187. (, stereochemistry of the product is:
-h
s\
H CHs
(a) Diastereomers (b) Racemic mixture
(c) Meso (d) Pure Enantiomers

188. +t- Producvs obtained is'lare :

U
s\
H CHs
(a) Diastereomers (b) Racemic
(c) Meso (d) Optically pure enantiomers

189.

cHz
.,,w
(c) (o)m
cH-cH3
cHs
I

19o. CHs
-cHz -cHz -.rra cHg-,cHz--oH-+--,jf],, Product (A) is:

(a) CH: :CH-CH3

-CHz -CHz -CHz-l
cHs
(b) CH3-CH2-CH z_-CHz_-CH : . (:X:
(c) CHs :CHz
-CHz -CHz -CHz-C
6,,
CHs

:CHz
I

(d) CH3 CHz

- atCHs-CHz -C
191. CHs CH : CH CH3 HBr ,
- - R2o2'A
(Anti -Markownikoff s addition)

Comment on optical activity of the products:

(a) Racemic (b) Diastereomer
(c) Meso (d) Optically pure enantiomer

rsz.
@ (A)
(major)
; Product (A) is :

OH

OH
RCO3H
Racemic mixture
Hzo

193. A
(alkene) Cold dil. KMnOa
Meso-compound
Alkene (A) will be :

(a) cis-2-pentene (b) cu-2-hexene

(c) crs-4-octene (d) rrcru-2-hexene
o
ts4. /\ + PPh3 (A)
-+ (major) + POPh3
Hlrrr,'l--JuttMe
MeH
Product (A) is
(a) rraru-2-butane (b) crs-2-butene (c) l-butene (d) Iso-butene
195. In which of the following reactions, r$/o products will be formed other than phosphonium
ylide (POPh3 )
o

,r$ +Ph3P:cH2--> (b) CH3CHO + Ph3P : Q

I
-CHs
+
cHs
o o
ll il
G) Ph H + Ph3P : CH Ph-----> (d) H-C-H+ Ph3P : CH CHs ----+
-C- - -
196. To carry out the given conversions, select the correct oPtion:

II
Rl
-C-Rz+R2CO2H
o
*t\ // o- o\ ./H il
CC Rl-C-Rz*Rz-CHO
R/ \ 1Rz OH
o./
\ I
R1-CH-Rz * R2-CH2-OH
(a) a = A8zO, b -ZnlCHaCO2t{, c = LiAIH+
(b) a =HzOz, b = CHg -S -CH3, c = NaBH+
(c) Both (a) and (b)
(d) None of these
197. The product (A) of given alkoxymercuration de-mercuration is :

CH"
l"
(1)Hg(ozccF:)z' CHgoH
n , (A)
\./ (2) \aBH4, Ho- (major)

,",&ocH3 *,5*' ,.,d

ONa

19g. cH3 -{:cHz

I
HC-GH , '. ,-ffi7if*
End product of the reaction is :

(a) HzC :CHa :CH2 (b) CH3

-CH:CH-CH:CHz
cHs
(c) HzC : CH CH : CHz (d) H2C : CH CHz CH : CHz
- - -
1.99. Major product of the given reaction is :

H2C:CH-CHz-t+F
"lt-
(a) CHs
-QH-CH2
(b) cHs
-9H
I
-CHa
II I

(c) CHs I (d) I-cHz-cdH2-cH2-I

-CHz -CH2 -
 (a) decreasing, decreasing (b) increasing, decreasing
(c) decreasing, increasing (d) increasing, increasing
2OL. Major product of the given reaction is :

H2C:CH2+Lan, '*A , Product

r"'-Fl I

,rrx
cHs
I

,.rX (d) H2C =C{H2

I

*CHz -CHs

2o2. A+
\r/
Ph3p:cHz---+
J L (A)
\rar.',:

Major product (A) is :

,ro ,rro (c)

2O3. In the given reaction, only one alkene undergo preferentiai oridarion br- elecrrophilic
ozone. Identify product (P) of the given reacrion:

.ry
OMe
o3
(P)
Nde2S, -78'C then NaBH4 (>52o/o)

(a) f.orn.
/^/'cHo
(b)

o
il
(c) CHs :
-C-CH, 'l-CH C
-CH2 -CHO
OMe
OH
I

(d) CH3
-CH -CHr'l
_- CH: C CH2 OH
-CH2 - -
OMe
rfmnCIGlmBofir$ ('Ar.KEIvEs)

HCr >,jl},, product (p)

za4. z--cu:= cH2- is:
+ci{?---cH
OI{ Cl

,,,,([] ",,,,@ ,.,(E

Cl
|
----(
,0,ffY''
. :r-\ c{-}''ti
2o5. ( ,;;u,.o;-'(A);lvla.i'rr product of the reaction ls:
J

,,,ru--T"'
,u. *,fi^
-.-/',rtor
T
.t
t'" [ -, A
-l'

r":!\-.."r\(:i,j.=.,
1--^-'..'-*.
i L,. .,0,[-
,n

V- oto
ull
,,^.* -l
2116. (^a€aoMe
(V_j
,-u" ,(A) i{'oo ,(B)
Pd-Basoa
\,/
Product (B) is :

oHo
(a) Ph --
ill
tltr-l- (:;[{ H (b) Ph -- CH :
'. CH - CHz - C- CH - CHO
(c) Ph * (cI{ ,-', Cl-l) .? -ci{O (d) Ph - (cH = cH) s --cHo
2O7. Isoix.:tene. in the lrlesence of H2SOa, forrus a mixture of two isomeric alkene (CsHro). The
majol ailiene ts :
crl.J cI{q cI-I3 cHs

(ai CHq ---

il
C-*UI{ C-"C}I3 (b) CHs
I
I
I

- -C.-CHz-C:C[{z
I
I i
(-lH
r cHs

cI"I3 CHs
ii
!l ?", 9H,
(t) CHr -Cl'l--CH : CH--CI{-CH.r :C *-CH z --Clf,z-CH
I

(d) ClI2
-CHs
 cH3, CHs

,+ ,,+
alkene

(a)

+ ,.,+
o
ll ,cH"
u-c-cu/tcH,
zos.
O -ffir-ra
Product (C) is
CH3-CH2-Br -ff$,rcr

OH OH
OH OH

OEt
H-k
(c) [,x-,< oH
(d) Both (a) and (b)
t J,rrtlOH
_
2lO. The following reaction take place in netas.
ligtr

Y
Use your knowledge
!v
n
_of
seen this reaction before
-iy%product
alkene chemistry to predict a product even though you have never

co2cH3

HgOAc
 {ffi}
co2cH3

(d)

OH

oo
,,llllllllll oo oo
2tt. !'lo'
(2)Zn
,H-t-c-H+cH3 -c-c-cH3+cH3 pyrualdehyde
-c -c-H
Glyoxal 2,3-Butanedione

What is the ratio of glyoxal to pymaldehyde obtained in the above reaction ?

(a) 1:3 (b)3:1
(c) 3 :2 (d) 2:3
CH,
l"
2:r2. (A)
-*--+ Products
O =*-
Which of the following product cannot be obtained in above reaction ?
o o o o
il il lt il
(a) H-C C (b) CH,
-CH2o - -H -C-CHZ-C-H
il
(c) CHs H (d) None of these
-QH I
-C-
CHO
CHs:' + - OsO, (10-a mole)
zlg. nt"t
(1
u
cH{ - "-ar, TMAO
(0.034 moles)
2, 3-dimethyl-2-butane
(0.025 mole)
(TMAO -+ trimethyl amine -N - oxide)
Product (A) is :

cH3 cH3

(a)
cHg\- .zcHs
(b) CHS
tl
'"'rr{\o/-ar,
-C-C
tt
-C-C-CH3
OH OH
o o
il il
(c) CHs (d) cH3 c(cH3)3
-C-CH3 -c-
.,###i

HO
214. Hso*
--+
Product (A) of the reaction is

(d) None of these

215. - ,=U_
(A)
,ma_lor)

Product (.4) is :

,"rA *,e(
,.,4 ,.r5
cHe\ CH: -_. cH::.
27.6. -C : CH-. CHz : CIlrL
(1

-C
cHr' cH30r' -
cH3o CHr/
(o) (b)

Arrange the above in the decreasing order of reactir.irv tou'ards HBr :

(a)a>b>c (b)b>a>c
fil b>c>a (d)a>c>b
217. Which reaction has the lowest AGt or (Activation-Energy)?

Y Her, \f Y HBT,Y
ta) .L, .l_, Br
Br

(c)
1
T{Br
--?
^

{il)*-
Y HEbY
\
^-/ Br Br
2L8. Which of the following will rearrange ?

,,,? (2)t
(a) 1 G) 1and3
(c) Nl (d) 1 ,2, 4,

21-g. Which of the foilowing is most likelv to undergo a favorable hy'dride shift ?

r-ll (b)
(u)
*{. X/,
@4 ray
(d) n .._
@

ZZO. Energy profile diagram for dehydration of 2-butanol using conc. H2SO4 is given below :

rcl
a
Me - cH2 -- CH
?' I

cHs
C
b
Me - CHz- CH - Me

Reaction co-ordinate

Product (b) of above reaction is :

(a) 1-butene (b) cu-2-butene

(c) trans-Z-butene (d) iso-butene
 How many alkene on catalytic hydrogenation given isopentane as a product ?
(a) 2 (b) 3
(c) 4 (d) s
222. Which of the following would not rearrange to a more stable form ?

b)HN
+
(c)>4 @)1
223, Consider the following reaction.
cs, ct12+ sbFa
BTCH2CHTF + SbF,
*L+ -
\.,/
In this reaction SbF, acts as:
(a) an acid (b) a base
(c) a nucleophile (d) an electrophile

224. (x)
-ffi--rMajor(Y) -##-- Major(Z):

Product (Z) is:

,rrrj}

(d)
d'
225. CH3-C:C-H \a\H2
> cHs-i ),^rffi,::
Relation berween (B) and (C) is:
(a) Enantiomer (b) Diastereomer
(c) Geometrical isomer (d) Meso
 The reaction of HBr with the following compound would produce :

,^,@o'
uBr
ro,ff*
,r@" \J Br
Br

Br

Hzo>
*Br2
227.
O 5" is an example of:

(a) Nucleophilic addition (b) Nucleophilic substitution

(c) Electrophilic addition (d) Electrophilic substitution
(e) Free radical substitution
228. Olefins can be hydrogenated by :

(a) Zinc and HCI (b) Nascent hydrogen

(c) Raney Ni and H (d) Lithium hydride in ether
 1. (c) 2. (d) 3. (c) 4, (d) 5. l(b)16" (b) 7 (c) L (c)
9, (c) 10. (d) 11. (b) 12. (d) 13. l(c) 114. lttrt t5 (t''.! IS (cj
17. (d) 18. (d) 19. (b) 20. (d) 2l (b) 4 22 (tt t3 t
.{
I [:
.
] 2.{ {h)
25. (b) 26.. (b) ,?,
Al. (d) 29. (b) 29. 1(d) Ieo (lt'r ;_1 I ( i' j sg i1:i
33. (a) 34. (b) 35. (b) 36. (b) 37. | (b) I 38. I ru; s9 (1" I 4i) ih)
4r. (d) 4?,. (e) 43. (c) 44. (c) 45 (a) 46 (c) 4.7 (cj 4S (b)
49. (b) 50. (b) 5L. (b) 5X. (a) 53. 1(b) 154 (dj 55 (i.rl s6 I t'1

67. (c) 58. (b) 59. (c) 60. (a) 6r (b) 62 LLl,i 5* , e") {i4 tr,i
65. (d) 66. (b) 67. (d) 68. (a) 69 (c) , 7a (r.l) /t t.Ll I r:* (cl
7g. (d) 74. (c) 75. (a) 76. (c) 77., (d) I 78. I tr,; 79 i'J l {i{.$. iri)
81. (c) 82. (b) 83, (a) 84. (a) 8s. l(a) 186. l(.i) 87 rb) 88 (b)
89. (c) 90. (d) 91. (b) 92. (b) 93. I(a) 194. ltul 95 t i.l ,l 96 (d)
97. (b) 98. (a) 99. (c) 100. (.1) 1 o1.. 1 fUt I Loz. l tt, t 103 Irll 'I
S4 {bl
105. (b) l06. (c) 1o7. (b) 108. (b) r.oe.l rat | 110.1 ca: tlr (c) tr?"i ru
113, (a) I"14. (b) r15. (c) 116. (a) 117 .l rul I 118.1 ru rl9 {h) 120.1 fcit
t2l. (b) t22. (c) 123. (a) 124. (b) 125.1 ra] lt26.l ra) 127 rb) r28.1 (c)
tzg. (d) 13(}. (a) 131. (c) 132. (d) 133.1 (.1 1134. I ra i 135 tri t r 36" I (.;
I.37. (b) 138. (d) 139. (d) L40. (b) 141.1 fUl lt42.l ti,; I4*e (i, I4.X.l irrl
145. (b) 146. (c) 1.47. (b) 148. (a) 149,1 ral lr5o.l tr,; lst I Itr-l
153. (c) 154. (c) 155. (b) 156. (c) L57.1 (ol | 158.1 (o.t 3.s9 i.\ i 6rl. i

161.
-:'1-
(b) 15.2. (c) 163 ft) 164.
165.1 tal 1166.l rur 167
(d) fbl 168.1 ,.
169. (c) l7a. (b) 17l. (b) 1.72. (d) 173.1 tUl lt74.i r.) t7t ire 1 ,u
177. (h) 178. (c) 179. (b) 180. (c) 181.l tul lt82.l tr,l 183 184 i
I

,,.r
185. (c) r86. (b) L87. (a) L88. (b) 189.1 (b) l190.l if,l 191 L92
r
ilI;
ra I

193, (c) !94. (b) L95. (c) 196. (c) t97 .l fUl I r98. I r;r i99
201" 2$9. (c) 203. (b) 2A4, (d) 205.1 fUl 1206.l r., Ltr t
(c) 2C8
209, (b) 210. (b) 211. (c) 212. (c) 213.1 rnl 1214 (at 21s [,' 21 6. I rb)
217. (d) 219. (c) 2r9. (a) 224. (bl ?.21.1 ft) 1222 (c) 223 tl ) 224.1 f .l
?:il (b,c)
?9J I9) I Y7:L (c) 2?9J (c)
 T*

1.
C. Hg(Oec)2 in H2O D. B2H6(BH3 )in ether
F. KMnOo in H2O G. HOBr H. NaBHa
In each reagent box write a lefter designaring the best reagent and condition selected from
the above list of reagents.

(cHs )2CHCH(CI)CH,
2-Chloro-3-methyl butane

(CHs )2CHCHBTCH2BT
1, 2dibromo-3-methyl butane

(cHs )zcHCH 'CHz (CHs )2CHCHOHCH2BT

3-methyl -1-butene 1, bromo-3 -methyl 2-butanol

(cHs )2CHCH(OH)CH3
3-merhvl-2-buranol

(cHs )2CHCH(OH)CH2OH
3 -methyl -1 , 2-butanediol

2. Propene (CHs be transformed to compounds (a to j) listed in the

left-hand column.
-CH:CHz)can
Write letter designating the reagent, you believe will achieve desired transformation. In the
case of a multi step sequence write the reagent in the order they are to be used.

CH3CHBTCH2BT Hg(OAc)z in H2O

(cH, )2cHoH BzHo in THF

 .ei cHscHzCHzOH retrillll
;!58.ri.l NaBH4 in alcohol

d. cH3cocH3 Br2 in CH2CI2

Gi cH3cHzcHo ii iii HzOz in aqueous base

ii:, i. ri:tlir:]}: iirliiititi i

4.
,,ll ' CH3CH(OH)CH2Br ti,$-#grgi HOBr (NBS in aqueous acerone)

Eiriiffiiii
(CHg )2CHBr ffi
:?irlina:it.:j:rr!

riiiliijlilii,ii I
, :l r,

HBt,.inrCff
' ::'::

;fl,

ilfii cHscH(oH) CH2OH Osoa in ether

Tffii

iln
CH, *6g2 -CH2 -Cl
ffi Thionyl chloride (SOCI 2)

lJ;, CH3 -C =CH two NaHSO3 in aqueous acerone

iii:i1 iirl i i

r(. NaOH in alcohotr and reflux I

t NaNH2 (sffong base)

i

t
ITTtrDROCIIRBOtrS (IILICMS]
3. In each reaction box write a single letter designating the best reagent and conditiorl selected
from the list at bottom of the page.
(F.S., -+ frrst step, S.S -> second step, T.S. -) third step) r

OH
ES. l-l /*cHs
ex-'"' S.S.E
(-l- ocH3

F.s. n
_>
S.S.E
T.S.E G:,'
e!-"'
F.S.

s.s.

r-l
_>
F.S.
_>
l-l
r-l
t"'
s.s.fl

G;
ES. l-l
S.S.E
r.s.[f

A. NaBH4,/alcohol B. Ph -COSW CH2CL2 C. PCC D. CH3ONa/CH3OH

E. B2H6 in THF F. H2o2laq. NaOH G. HsPOa & heat H. AlCl3 /C6H6

I. Os in CH2C12 J. Br2in CH2CI2 R. 2Oo/o KOH & heat L. Ph - Li,/ether

4. Match the reagents a-j with products A-J. There is one best product for each reaction.

The molecule (x), is the starting material for all reactions in problem. Do the ones you know
first and then tackle the rest by deductivee reasonm
reasoning

H2O heat, pH 7
{a}
HO- -:
(b)

(c) tBuOK polar: aprotic solvent

(1) Os, ether

(d) (2) HzO NaOH, HzOz

(e) Br2,CCla

(o NBS, hv, CCla

(1) Hso(+)
G}
(2) NaOH, HzO

(h) (1) BHa, erher

(2) HzO 2

(1) OsOo
(i) (2) NaOH, HzO

t, H2/Pd/c(EtoH)
Match the column:

CH3 : C-CH3 crs-produet with H2l Pd - BaSOa

-C
CH3-{Hr-C-CH Trans-product with Na/liq. NHs

CH3-C -CH lqV[ite: With amm, AgN0 3

CH3-C-C7Et H2 gas with Na

i[fi+i-lit+tiiiiffi +li++l+l=*tllilffi i*Fr$1f$+*++*,
Match the column I with column rr and with column rrr (Matrix).
ij]jrr,ti.ritjilji I iilj;l:iji:,1111:xj,;,,i1;illi,.+lj:ii.r:j i'ffi
.j..,1jr.1. .,, . : : 1::.1 rt.i.all...r.;,,:.i.,......

7. Match the column I and II.

cH2 oH
I
-
8. (1) __H--+rel (2) "* , (B)
O A

roH OH

A
I

(3) T'tc) (4)

oHoHa O--r-e1p;
t;grn e{{Fql*c*l+t tg**g ef S*Br-Sr,n:[iis'-A*-4-t 8 t P) -ip e!He! ]9*i
 (2) CaHs (alkene) --II-z-*(B) (exclude stereoisomer)
(all isomers) Ni

Total number:of products A and B (i.e. A + B) is ecual to :

L0.

$$fi* lil

CH
CH
Il tc*l --Ea--+ tpl
ccl4 ll (rans) "' , (Q)
cH CCl4
CH

ft ffi$#ii rir It*fiffiuui,il

CH
CH
il (crs)
--I*j
CCI,
1s;
il (rrans) "' , (S)
CH ccl4
CH
I
I
CH 3
CH 3

Sum of products P, Q. R. S (i.e. P + O + R :+ $l is enual to :

 Vladimir Markovnikov rule ;
Alkenes undergo electrophilic addition reactions. It is triggered by the acid,acting as
a electrophile toward n-electrons of the double bond.
Markormikov's rule sgtes that when an unslrynmetrigally sybstilllte$,alkgne reacts
with-a tiy{trgin halide, the hydrogen atbm adds to the carbon'that has ft€:greatei

I-. tcHz

Mechanism :

Step - L

Step- 2
@
!' ' lA.rcH'
L--Acr
(fast)
".,#@

A. Which of the following is most reactive toward Markovnikov addition

,ro
?

(a)o .,,O (oG

B. What is the energy profile for the given reaction ?

(b) I
E

A
Reaction co-ordinate

(c) I (d) I
E E

\
Reaction co-ordinate Reaction co-ordinate

C. In which of following reactions carbocation rearrangement is possible

-CH
?

(a) (CHe )rCH CH : CHz -+--> O) (CH3J-J

)rC CH,o ;JY_+
- 0.C - - O.C7Cla

(c) Ph CHz CH : CH,

-#? (d) All of these
- -
*

D. Identify the major products r.,, r, and r, in the given reactions.

e)-": cH3oH
f2

HBr
f3
Dzo
oH oD
,,,d"i
d"',d*'
,,,d"id*'d"'
cHs cHs
(c) in all the reactions (d) in all the reactions

In which of the following reactions, product is racemic mixture ?

(a) cHe -cH, -cH:cHz -+fl- G) 'T>.:.<L,-ffi-

\
C[J3
zcHs riBr
(c) )c : c1
\!'/ u/-r.iri\H *,-" (d) All of these

F. In which of the following reactions, diastereomers will be formed ?

cH"
*-J-tI

fr'
CH

,,,el:;"-#r-+ 6 (b)
-#"
Br

,,4-ffi-, (d) All of these

 ;CHz *fH*CHs
s@
CH*.-*CH, .-CH *iCH2 +CH3O* -+CHs ,t

ocH3

Consider the above reaction and answer A to E.

A. What is electrophile in first step ?

(a) cH, (b) Ho

- 3, -
(c) cH, cHz cHs (d) Hoo
-
B. \,Vhat is nucleophile in first step ?
(a) CHrOH (b) l-butene
(c) HzO (d) cH3 -o -cH3
c. 'What is electrophile in second step ?
@
(a) CH, (b) Ho
(c) cH,
- cHz
- 3, - cHs (d) cH3
-cHz -cHz -3r,
D. What is nucleophile in second step ?
(a) CH, CHz o) cH3oH
(c) Hro -CHz -CH - (d) cH3
-o-cH3
E. Which step is rate determining step ?
(a) attack of nucleophile CH3OH (b) attack of electrophile Ho
(c) attack of nucleophile HrO (d) attack of electrophile 3u,
*:fi'#

L3. Match the column I and II :

1. - G; (iv) - C; (v) - F
(i) - A; (ii) - B; (iii) .

2. a-D; b-A, C; c-B, E; d-A, C, F; €-8, E, F; f -F; g-G; h-I, K; i-B, E, I; j-D, L
3. Reaction 1:B,D; Reaction2: E,F,C Reaction3: I,A
Reaction4:L,G Reaction 5 : B, L, C

4. a-C; b-D; c-A; d-F; e-I; f -J; g-E; h-H; i-B; j-G
5. &-p, Q; b-r, s; c-r, Si d-p, q
6. ?-r, s-z; b-p, s-y; C-p, s-y; d-q, s-y
7. a-r;b-p, c-q;d-s 8. A+B+C+D=3L2
9. A+B=5 10. P+Q+R+S=B
1L. A-b; B -c; C-d; D-b; E-d; F-d 12. A-b; B-b; C -c; D-b; E*b
13. a-q; b-p; c-s; d-r
 ,,rycH:t",0, Uc-cH,.,
2. \,A.. Brz (D alc.KOH
ry
(A); Product (A) is :
,o,Ql''
cdT (d N"Nrt--?
major
(a) HrC : CH CH : CHz (b) cH3
- -c:c-cH3
(c) CH,
-CH, -C - CH (d)CH3-CH:C:CH2
B. n*
cH3cH2c-cH
-ffi"r+r ,(K)
Product (/0 of the above reaction is :

,o OH
c Et
.)).c-
(a)l -
I *, Ac:c-Et
 iir':liriiirii iiiil it
g#.$

OH OH

,r al'c-c-CHz-cH: (d) dl'c:c-cHs

4.
- C:
CH, CH, CH, (A) (cH,),so*
- - CH +
llil,f_r---r ,,r,
amide

Give the structural formula of compound (B) :

(a) CH, (CH, )z : C SO3H
(b) cH3 - (cHz )z -C _ c _
_c - cH3
- o
(c) CHs
-(CHr)z -C - C-CH2
-o- !-,
(d) CH3
I
-CH, -C -C_CH2
,?-'CHz-CHz-CHe
5.
-*o
(a) NaNH2, CH3CHO
(c) KOH, CH, CH, __ Br
; This conversion can be acheived by

(b) waNHz, CH,

-CH,-CH2_-Br
:

- (d) KOU, CH2-_ cH2

I
Br
t'
Br
6. which alkyne will give 3-ethylhexane on catalytic hydrogenation
?

(.)\av
\
(d) All of these

7. Reactant p gives products e or R.

a
The possible reagents are
(D 2Na/liq. NH, (D
H2 lPdlCaCO, (quinoline) (rrr) 2H2lPdlC
The correct statement with respect to the above conversion
isy'are :
(a) Q is obtained on rreatment with reagent (I)
G) n and Q are obtained on rreatment with reagent (II)
(c) R is obtained on treatmenr with reagent (I)
 (d) n is obtained on treatment with reagent (II)
8. Br-(CHz)rr_c: cH N"NH, ,{a)-ffi-+(B);product (B) is:

(c) (d) gr-(CHz)-CU:CHz

9. Ph
- C
- CH -+H-, Major product of the reaction is :

(a) 'l>':'(l (b) ':>:.11

(c) Ph-C-C-OMe (d) on -, - cHz
CI OMe

10. ph-c-cHs 3NaNH2

I

> @) ;product (A) is :

I nroduct

CI

(a) Ph-CH:CHz (b) Ph-C-CH (c) Ph-CH2-CH, (d) Ph-C-8rf,

11. Which combination is best for of the compound (A) shown below ?
%;l,r*,ton
u
4t,
r-,
" -/a cH2cH 2cH2c: cH
-
cH3cH2 (A)
H
(u) Hrc -3f- cH2cH 2CH2BrNac
- cHr(A)
(b) " 31-cH2cH2c H2BrIut - t'r(A)
I
cH3cH2 cH3cH2
H cHs
4.. 4.,

't
(c) HrC r--i
- Br
-
2. BTCH2CH:CHrC-CH
iHs
A) (d) Hr'p-g
I
1. NaNHr, NH,
2. BTCHTCHTCH2C-CH
A)
, cH3cH2 cH3cH2
12. Which one of the following is the intermediate in the preparation of a ketone by hydration of
an alkyne in the presence of sulfuric acid and -e.cury (tD sulphate ?
 _. _i -

(Ar,mrEs,
:

(c)

13.
o - cH2
- c: c
- cH2
- cHz
- cH2
- Br

To carrl, out above conversion, (A) and (B) respectively, are :

(a) NaNH ,,Cl CH, CHz CH, Br

(b) NaNH z, F - CHz - CHz - CH, - Br
(c) NaNH2, I-CH2- - - - Br
(d) NaNHr, I-CH2-CHz -CHz -
-CHz
l2
-CH2 -I
14. H-C:C-Ph Product; Product obtained in this reaction is :

H-uCo
Ph-C -CH-I (b) h-CH-CH,
(a)
I

I
P
t'
I
-I
(c) Ph-C:C-I (d) r
-C-_C-H
(i) NaNH2, NH, H2
LE. Gc:cH (ii) CH.Br Lindlar catalyst
B) ; Product (B) is :

!-.-cHs T I',,
(a) \ G)ffC:c
'"'(., H
)
CH:
1"6. Which of the following alkyne on treatment with H2(2 mole)/ l/ Pt gives
si an optically inactive
compound ?
(a) 3-Methyl-1-penryne G) +-Vtethyl-1-hexyne
(c) 3-Methyl-1-heptyne (d) None of the above
, (4;
Redhotcutuue
1.7. cac, "o , (B) , Product (B) of the reaction is :
(Calcium carbide)
(a) Toluene (b) Ethyl-benzene (c)
Benzene (d) Buryne
18. What is the final product, C, of the following reaction sequence ?

\ I.NaNH,
2-HfH;B;----?^
lta, NH:(liq.)
-r-r O ,g

B-#-,c
Br Br Br

caiSBr cor-rf-[ c.r*i NHz (d)S Br

le. compound m-h C>-
L-
cHz-cHz-cH2-CH3
I I AgNol
I
o oo oo o
ll
H- -PreciPitate
C CHz CHz
t! il iliI ii cHo
C _ C _ H + H_ C_e_ O_H + H_C_ O_H *1"-
- - - CHO
Compound (D will be :
,", GcH: cH-c:cH o) CEcH-CHz-c-cH
(c)GcH-cHz-c:cH (d) cH-c:cH
C=c-
20. Choose the sequence of steps that describes the best synthesis of 1-butene from ethanol
-
(a) (1) NaC CH (2) Hr, Lindlar
:

- ; Pd
(b) (1) NaC CH ; (2) Na, NH,
-
(c) (1) HBr, heat ; (Z) NaC : CH ; (3) Hr, Lindlar pd
(d) (1) HBr, heat; (2) Koc(cHs)3 , DMSO ; (3) NaC:cH ; (4) Hz,Lindlar catalyst
21. Which allqane yields butanoic acid (CH3CH2CH2CO2H) as the only organic product on
treatment with ozone followed by the hydrolysis 7
(a) 1-Butyne (b) 4-ocryne (c) l-Pentyne (d) 2-He>ryne

ro) -+-+ GcHz-cHz-."rV

unit of unsaturation in ."fiitifo"to1',
(a) 7 (b) 8 (c) 9 (d) 10
o
ll

2g. ll > H.o* (A) "uoH > lgy

Kolbe electrolvsis
> , ,r,
Proa%t (C) of above reaction is:
(a) HrC : CHz (b)cH3-c:c-cH3
(c) HC CH (d) CH3 :
- - CH CH - CH,
24. To convert 1-burpe to 1-D-butanal, one would carry out the following steps :
(I) Sodium amide, then DrO
(II) Disiamy lborane, then hydrogen peroxide/sodium hydroxide
(III) The transformation can not be carried out with the indicated reagents.
(a) I, followed by II (b) II, followed by r (c) III (d) II
25.. An unknown compound (A) has a molecular formula C o Hu. When (A) is treated with excess
of Br, anewsubstance(B)withformulaC.*H6Brr isformed. (A) formsawhiteppt.with
ammonical silver nirrate solurion. (A) ma)-be : '
(a) But-1-rne (b) But-2-yne
(c) But-1-ene (d) But-2-ene
26. One moie of 1.2-dibromopropane on treannent with X moles of NaNH, followed by
neatment rrith ethl-l bromide gave a pentyne. The value of X is :
(a) One (b) Two (c) Three (d) Four

9H:
: CH
I

- CH
CH,-_-, - C excess HBr .
27.
The product of the above reaction is :

QHg Br Br CH" Br
l"ll
(a) CHg - CH - CH - CH2
l"l
(b)CH3-CH-C=CHz

CH" Br CH" Br
l"l l"l
(c) cHs-cH-f -.r, (d) cHs - cH - cH, - cH
'l
Br Br
coldKMnoa
28. CHs C rl4l
-C - -CHs
Product (A) is:
oo o o
(a) llllllll
CH3-CH2-C-C-H O) CH3-C-C-CH3
OH
(c) tt
CH3-CH-CH-CH3
OH
(d) O : CH : O
-CH2 -CH2CH
29. In which reaction last product is Ph C : CH ?
Br
-
I
NH4cr
(a) cuH,
-g -cHs -";ffi""*--
I
>

Br
(b) C6H5CH : CHz ccl4
3NaNH2
Mineral oil, heat
___-
NH"C]

o
il PCI 3NaNH2 NH,Cl
(c) CoHs q

-C-CH3 Mineral oil, heat ---+

(d) All
 Predict the product of the following reaction sequence.
(1) excess NaNH,
eth
(2) excess I-CH2-(CH 2 )2-CH"
(3) H@

(a) 6-iodo-1-hexyne (b) 1-hexyne

(c) S-decyne (d) 1-iodo-1-hexene

1. (b) 2. (b) 3. (b) 4. (b) 5. (b) 6. (d) 7. (c) 8. (c)

9. (b) 10. (d) 11, (b) ,r. | (d) 13 (c) t4 (c) 15 (c) r6. (a)

17. (c) 18" (a) !9. (a) 20 (c) 21 (b) 22 (c) (c)

25. (a) 26. (c) 27. (c) 2A (b) 29 (d) 30 (c)

 SubsUtution Reactions (S*,,t",, S* )
ET

1. Which of the following is not expected to be intermediate of the following reaction ?

I
Hzo
---+

,"rd ,rro ,.rd

i + NaI Acetone
^- ) L
product;' S product of the reaction is :
CHs ^z
cHz - cHs
 cHs 'r cr{?
r--l--H H I r+-H
9Hs
(u)
H-t-cH, rul n ' IIJ cHs (c) (o)
arr-fn
cHz - cHs CHz _ CHg cHz - cHs cH2 - cH3
3. Rate of S*z will be negligible in :

Br Br

(a) (b) ,.rO (d)

O
4. what is the major product obtained in the following reaction ?

d:-t'--*#-product

cHs
I

5. Cl -CH2 -C -CH2 - CHz - Cl + I- DMr- product; Major product of this reaction is:
I

cHs
CH^ cHs
t'
(a) I-CHz -f -ar, -CH: - Cl
I

(b) ct -cHz -c -cH2 -cH2 - r

I

CH, CH,
cHs cHs
I

(c) H2C=C-CH2-CH,
I

=61 (d) Ct -CHz -C -CH2 = CHz

I

CH,
Which of the following expressions is representative of the rate law for a S
*z r€oction ?
(a) Rate - k [electrophile] (b) Rate = k [electrophile] [nucleophile]
(c) Rate = k [nucleophile] 2 (d) Rate =k[electrophite]2
Acetone
7. NaI (1 mote) >,jfL,, Major product of this reaction is :
*rtk*
,,in{}I ronQ,! (c)#Gl rorbO<,n
 8. Which ,n;rlrjlowing alM halide undergo rearrangement in S *r
"t
u

t
(a)cHs-f
eI:,,.r eft n,,,1rr,.Lr
cH-cH3O) (d) All of these

g. ,r"T;"ling
Arrange three chlorides in decreasing order towards S
*r reoctivity.
(l)Ycr (2)ry CI
G)a CI
(a) 7>2>3 (b) z > 3 > 1

(c) 2>7>3 (d)s>2>l

1"O. Which compound undergoes nucleophilic substitution with NaCN at the fastest rate ?

,u, ,r.', rul

Br),/:,n (c) ,r--X.,^. (d) BrX\r .'
'X
11. Rank the following in order of decreasing rate of solvolysis with aqueous ethanol (fastest -+

f'' 1l<"'
slowest)

H2c=C-Br \-,/ \Br I'

CHs -CHCH2CH(GH3)z
(1) (2) (3)
(a)2>1>3 (b) 1>2>3
(c) 2>3>1 (4) 1>3>2
12. The reaction of 4-bromobenzyl chloride with sodium cyanide in ethanol leads to the
formation of :

(a) 4-bromobenzyl cyanide (b) 4-cyanobenzyl chloride

(c) 4-cyanobenzyl cyanide (d) +-bromo-2-cyanobenzyl chloride
L3. Which of the following reactant will not favour nucleophilic substitution reaction ?

(a) (b) Ph - Br

Br
cHs
I

(c) CHs -C - CH2 - Br (d) All the above

I

cHs
Br

1,4.
+oH-
H H
(r) (D
 Conversion of I to II :

(a) takes place by S*r (b) takes place by S *e

(c) takes place both by S *r and S *z (d) does not take place
L5. Which is the correct reaction coordinate diagram for the following solvolysis reaction ?

d:: ""d;:+ d;,

Reaction Coordinate
(b)
^.ft
o"l

Reaction Coordinate

(c,L Reaction Coordinate

Reaction Coordinate

14c labelled
\
16.
oar:: OCOR
RCO"H
product; Product of this reaction is

OCOR
:

(c) both (a) and (b) (d) None of these

I
-l- -cH,
17.
ol'*u" (A) cnrs*u > (B) , product (B) is :
 I I

,", ,r,ds-cH3
dcH2-s-cH3
s-cH3

...,dcH"-Br (d) None of these

18. represents the correct graph for S *z reaction

Which of the following rt ?

log (rate)

(a)

CHg - Br CH3 - CHz- Br CH3 - CH-

I, _
CHs CH3 -C - Br
cHs

log( rate)
(b)

Ct{3 - Br Et-Br i-Pr-Br t-Bu-

log (rate)

(c)

CH3 - Br Et-Br i-Pr-Br r-Bu- Br

(isopropyl)
 log (rate)
(d)

cH3-Br Et-Br i-Pr*Br t-Bu-Br

19. Which of the following graph represents correct graph for S*r r€zlction :

log (rate)

(a)
CHs - Br CH3 - CHs- Br CH3 - !H- Br
I

cHg
1"
cHs-g-8,
I

cHs

log (rate)
(b)

CH3 - Br Et-Br i-Pr-Br r-Bu-Br

log (rate)

(s)

CH3-Br Et-Br i-Pr-Br r-Bu-Br

 log (rate)
(d)

cHs
pound in
S
*r f€ilCtion ?
(a) CHs -CHz -CHz -CHz -Br orCH3 -CHz -!H-CH,
Br
CH" cHs
t'
-CHz or
I

(b) CH3 -C -CH2 CHs -CH- CH -CH:

ll
Br Br

Br Br

,.,ooro
CH.J CH.J
I I

(d) cH3 -c -cH3 or CH3 -C -CHs

I I

Br I
22. What is the major product of the following reaction ?

H2C = CH -CHz -OH-;ffi-rProduct

Br
: CH -CH2 - Br
I

(a) CHg - CH - CHz -'Br (b) H2C

Br OH
I I

(c) CHs -CH -CHz -oH (d) cH3 -cH-cHz -oH

23. S*r and S*z products are same with (excluding stereoisomer) :

CI

(a)
G CI
*,eJ'
(c)

+ CI
(d) Ph - CH
lr,
-CH-CH3
It
24. Consider the nucleophilic attacks given below. Select in each pair that shows the greater S*z
reaction rate.
o
Br + -CN -cN
(A)
(r)
or -UA*3+(II)

(B) H3C-Br--SH or HsC-Br+CHTSH

(irr. (IV)

(c)GBr cr or A-o', + rI- in DMSo

\-rlr
(V) (u)

r,)GBr+cl- or GBr + I- in methanol

CVII) olrr)
ABCD .\BCD
(a) (I); (M; ffI); (ull) O) (ll) ; (lll) : Ol : (\{il)
(c) (I); (III); (V); VIII) (d) (l) ; (lII) : Ol : 011)
25. Which of the rwo stereoisomers of 4t-bur_v*lc-v-clohexr-l iodide ,'ll-l-) rvill undergo S^oz
substitution with 128I- faster, and why ?
H
1127

w' (B) H
(a) A will react faster because it is the more stable of the two isomers
1727

(b) A will react faster because it will yield a more stable product, and the rransition state for
both reactions is of the same energy
(c) A will react faster because the approach of 128I- can depart unhindered.
(d) B will react faster because it is less stable than A, and the transition srare for both
reactions is of the same energy
26. (Z)2-Butene reacts with Br2lH2O. The resulting bromohydrin when treaied
with
methoxide in methanol . underg:oes an intramo,-lecular S reaction. Taking into
*,
consideration the stereocheqri.cal consequences of the reacd]on mechanism in,Iolved,
choose the final product(s) of these rransformations.

o
(I)
rT;A;"' tu) nac,,iftg;, (uI)

(a) (I) only

,T;A:?,,
(b) (II) only
(c) (III) only (d) Equal amounrs of (I) and (II)
27. Rank the following species in order of decreasing nucleophiliciry in a polar protic solvent
(most -+ least nucleophilic) :

o
ll
cH3cH2cHzo- cH3cH2cH:S - cH3cH2c- o-
(1) 2 (3)
(a)S>l>2 (b)2>3>1 (cj l>3>2 (d)2>1>3
Identifu products of the gir-en reactions :

Reaction-1
e(:, CH -'---'-
.CC.]i.
cu,co-:-.
)product

.-..OTs
Reaction-2 ____-+
CH3CO2.\a
product
cH3co2H
NMe2

.,,G:XCHS \-cHs
o + enantiomer
NMe2

(b)
..Yttr*
enanriom.,,
NMe2
{1-o)fcHs
(c) single product is obtained in both the reactions

,.,fio\-cHs single product obtained in both the reactions

jail:r::rri:irii :i:iriiirr:i,i

.#,s

I
o
l]
(d
k
29. bo
o

CH3-X Me-CH2-X Me2CH-X Me3CH-X

Which of the following is true about given graphs A and B?
(a) A -+ S*r B -+ Sooz (b) ArS*2, B-+S*r
(c) A & B-+ E1 (d)A&B+E2
30. In each of the following groups, which is the strongest (best) nucleophile ?

(r) (1) H3C -O- (Z) AO- (3) H3 C -S- in CHrOH

(II) (1) oH- (2) H2o (3) NH, in DMF
I .o-
(rrr) (1) I (2) \o (3) CH3O- in DMSO
(a) I,3 ; II,3 ; III,2 (b) I,2;I1,1 ; III,3
(c) I,l;11,2; III,1 (d) I,3; II,1 ; III,3
o
81. @>_$ -,.rr)a-cH2 NaNH2
dimethory ethane
(A) ; Product (A) is :
(Major)
o
o o
,r, @l-r.rr)g
o
o
-cH=cHz o)
@ne o
(d) None of these

32. Which of the following reaction is an elimination reaction ?

H
Br KI
(a) * IBr + KBr
[frH "'oo, O-, Br
H
--------)

(.) NaocH,,
af:, Od.r,
(d) both (a) and (b)
 cr .ffii-
Bs' Product
+ cHz _
Which of the following products can be obtained from above reaction ?

(") L;l-cHz (c) ,o) Auorthese

- ocH3o) .rr$ U{."r'
34. What is the principal product of the following reaction ?

cHs
H4Br
H-J-H
I
+ NNs#Product
HT-CI
cHs
cHs cHs cHs

(a) H
H #n,
*, (b)
H
H (c)
r.rr--l-H
n#H (d)
H-J-
H--{-H
N,

H
I

-J-CI H H*cr cr-1-H

cHs cHg cHs
35. What would be the effect of increasing solvent polariry on the rate of each of the following
reactions ? (Nu = D€utrfll nucleophile)
(A) Nu + R * L-----+t$r-^ * r-
(a) increases (b) decreases (c) constant (d) cannotbeprediaed
(B)R-L@----+Ro +:I
(a) increases (b) decreases (c) constant (d) cannot predict
36. Which of the following is most reactive toward S*z t€action ?

(a) CHz = CH -CH2 -Cl (b) Ph -cH2 -cl

(c) Me - o^Cl (d) Ph - C- cH, -
il-
Cl

o
37, 4-chloro-1-butanol + NaOH -
"f--tal--l!C{UA-+tfl
Product (B) of the above reaction is :

(a) O ru)
rJ (c) 5lt" (d)
\ztH2-cH3
38. In the given pairs of alkyl-halide, in which pair the first compound is more reactive than
second compound toward S r€ilCtion ?
(a) (CI{s )2CHBr or CHs"z -CHz -CH2 - Br
(b) CHs -CH2 -CHz-Br or CHs -CHz -CH2 -I
(c) Ph - Br or CHs -CHz -CH2 - Br
(d) CH2 : CH -CH2 -Cl or H2C : CH -Cl
39. In the given pair of reaction in which pair the second reaction is more reactive than first
toward Srz reection ?
(a) CHs -CHz -Cl+CHs -CH2 -O- ---+ Et-O-Et (or)
CHz -CHz -Cl + CH3 -CHz -OH--+ Et -O - Et
(b) cH3 - cHz - cI + Eto- Et - o - Et (or)
-+
cHs -cHz -cl + EtS- ---) CHs -CHz -S - Et
(c) _Et-Cl+CH"O ---)Et-O-CHs (or)
(1m) tzl_l
Et-Cl+ CHrO--)
(2m) Et -O -CHg
(1m)
o
(d) Et - Br + ph.p-----+ Et - pphs (or)

Et-Br-Ph:N-+E+-frofr,
40. Among the follon'rng pair of reactions in which pair the second reaction is more reactive than
first in S.-: r€sCrion ?
(a) Me3CCl - H:O- \Ie.COH (or) Me3CBr - H2O---+ Me3COH
(b) Me3CCl * CH3OH--------+ \{e3C OCH 3 (or) Me.C-Cl * H:O
-

MerC-OH
(c) Me3CCl+ H2O -----> (or) Me3CCl- H20
(1M) (2M)
(d) All of these
4r. Which is a true statement concerning the transition state of an S
*z r€flction ?
(a) Ciosely resembles a carbocation intermediate
(b) The electrophile is responsible for the reaction
(c) Lower is energy than the starting materials
(d) Invoives both the nucleophile and electrophile
42. Increasing the concentration of a nucleophile in a typical s*z reaction by a factor of 10 will
cause the reaction rate to :
(a) increase by a factor of 10 (b) increase by a factor of 102
(c) decrease by a factor of 10 (d) remain about the same
43. Decreasing the concentration of an electrophile in a typical s *z reaction by a factor of 3 will
cause the reaction ratio to :
(a) increase by a factor of 3 (b) increase by a factor of 32
(c) decrease by a factor of 3 (d) remain about the same
44. Increasing the concenffation of an electrophile in a typical s^,2 reaction by a factgr of 3 and
the concenffarion of the nucleophile by a factor of 3-will chd'iige the reaciion rate to :
(a) increase b1' a factor of 6 (b) increase by a factor of 9
(c) decrease br- a factor of 3 (d) remain about the same I

45. Consider the follon ing reaction and select the best choice that represents the reaction.

Nao -scHrcH,
Product

9Hs CH" CH"

(a) H
cH2cH3 ,,,dil1i,.n,
cHq 9Hs
t' 9Hs
(.) s-cH2cHs
OtscH2cH3
I
(d)
04
rvr"lH
lx KSH )
46. n,lO Product: Identify the product.
H
SH H SH
ira"lH NIefH
I

HS \IC H|vr"
(a) ur-|.-, (b) e,fo (c) Et D (d)Et
I D
H SH H
47. The reaction,
HOH
--.X- + SOCI2
--+
+ so2 + HCI
proceeds by the........... nnechanism.
(a) S*i (b) S*z (c) sB, (d) S*r
48. Consider the following anions.
oO
q"
o
illl
CFs-S-cl-
"ll
CoHs -S-o- lt
cHs-c-o-
I!
oo
(I) (II ) (xr) (u)
When attached ro sp3-hybridized carbon, their leaving group abiliry in nucleophilic
substitution reaction decreases in the order :
(a) I > II> III > IV (b) t> II > IV> III (c) IV> I > II > III (d) IV> III > II > I
 CH" o@
" "rl"
PhsNa=-)
H --- Principal organic Product of the reaction will be :
Jo

Ph Ph
Ph
-]-
(c) H-l-ct
cH3 n-fcrr,
(d)H I Ph
I I
Ph Ph
50. Reaction of R-2-butanol with p-toluenesulphonyl chloride in pyridine followed by reaction
with LiBr gives:
(a) R-2-buryl bromide (b) S-2-butyl tosylate
(c) R-2-buryl tosylate (d) S-2-butyl bromide
51. The compound which undergoes S*r reaction most rapidly is :

c.i$,, curln,
(c) CH2Br rar$s,
52. Addition of KI accelerates the h1'droly'sis of primary a\'1 halides because :
(a) KI is soluble in organic solvents
(b) the iodide ion is a n-eak base and a poor leaving group
(c) the iodide ion is a strong base
(d) the iodide ion is a pon'erful nucleophile as well as a good leaving group
53. Which of the following phrases are not correcdy associated with S
*r r€action ?

(1) Rearrangement is possible

(2) Rate is affected by polanw of solvent
(3) The strength of the nucleophile is important in determining rate
(4) The reactivity series is tertian' > secondary > primary
(5) Proceeds with complete inversion of configuration
(a) 3, 5 (b) 5 only
,:, 2,3, s (d) 3 only
 (A) NBS (B) KSH (c)
-*3'-- > > , Product (B) is :

d
A
(d)

55. Energy profile diagram for an exothermic reaction, A -l-* g - :--15 3 , D, is given below.

t
PE.

Progress of the reaction -*

The rate determining step of the reaction is :

(a) A->B (b) B+C (c) C-+D (d) can not predict

cHg

s6. NBS>Jf]
@$
Major product is (A) is :

57.
,",Oa *,d"
Cl
-LiBr'zDMSo
S* z conditions
(c)

, Major product (X)

4 Br

The productX is :
 ,rr%r,
58.
",[\'2
Relative rate of reaction of the following amine with methyl iodide is:

A
1*j
(
(A)
N
/\n \,/*.-(c)
(a)A>B>C (b)A>C >B (c)B>C>A (d)B>A>C
H
PhcH2o\ \ 'ors

se. Hn
)1t'x!1.r,
I
Nal
Dimethyl sulfoxide

ocH3

Major product which you expect in the above reaction is :

H H
, \;ors o.r,nil!.., '
)c-"( 'g-<ocH3
2' -'\a.:o.n,
@) -J
tr' L
H I
(b) .)f
HH I

ocH3 ocH3
I
H
o.r.,rf,!..-n ocH"ptiLtr.. ors
).-'\ 'i"'2'ocu' \a - .-l
(c) ,1 (d) J' '.'<Y
L ocH3
HH t
ocH3
HS
\aOH in
(A)
60. aqueous ErOii
(major)
c6H1os
HCI
Major product of the above reaction is:
S

.,,o (d)
o
 o,
Yr
61. cHg-f-f'- - cHg --------+ Major product of the reaction is:
CH3 OTs
Ph
.nr),c_ lrq
(a) ,t'n
\CH,
(b) cH"-c-cH-cHz
"l
cHs/
cHs

cHs\ cHs\
l+r.'Ph ^ ^/Ph
u
cHr/L -- -rgt,
(d)
cHr/ -
ICJ C: C
\cHs

62. The decreasing order of reactivity of the compounds given belorv torvards soivolysis under
identical conditions is :
CI C1

cHg-9-CHs
I I

C
C1

O f -.r,
I

cHs -

A
(r)
HgC

(D
o
(rrr)
(a)II>III>I (b)I>II>III (c) III>II>I (d)II>I>III

OH

68
0G",,
1.One Eq. NaOH
(A); Product (A) is :
2 MeBr

(a) oH (b) OMe (c) (d) None of these

64. (R)-2-octyl tosylate is solvolyzed in water under ideal S*r conditions. The product(s) will
be:
(a) R-2-octanol and S-2-octanol in a 1 : 1 ratio
(b) R-2-octanol and S-2-octanol in a 1.5 : 1 ratio
(c) R-2-octanol only
(d) S-2-octanol only
65. From each of the following pairs select the compound that will react faster with sodium
iodide in acetone :
Pair-A: (1) 2- Chloropropane (2) 2- Bromopropane
Pair-B: (3) 1- Bromobutane (4) 2- Bromobutane

(a) 1,3 (b) 1,4 (c) Z3 (d) Z4

66. Among the given halides, which one will give same product in both S
*r and S
*z r€&ctions.
!', ,/\,/cHs
(r) cHs - cH -cH2 -cH-cHs ,,,, (_L.,
Br

(u)eI (M CHs -CH

I
- Br
Et
(a) (III) only (b) (r) & (rr) (c) (III) & (nD (d) (I), (u) & (IV)
67. Product(s) formed during this reaction islare :

*
CHz-CHz-OTs
1'oll
AcOH
,Product? [c. = isotopic carbonl
* *

,u qcHz-cHz-oAc G) qCHZ_CHZ_OAC
*

(c) (d) Both (a) & (b)

qtH2-cH2-ors
excess HI (conc')
68. Anisole reflux
Product

,",@r + cH3r
@r + cH3oH
",
r.l
@-oH + cH3r tal
@on + cH3cH2r

69. Which 9{ lt. following compounds would react faster with NaCN in an S*z r€oction ?
OMe
(?)X,.' ,0,$or, (c) M{N (d)$OTs
 HC
-CNa+Cl-CH2 -CHz -CHz - I ----+ (A); Majorproduct (A) is:
(a) H-C :C -CH2 -CHz -CH2 - I (b) CHz =CH-CH2-I
(c) H-C :C- CHz-CHz -CH2 -Cl (d) CH2 =CH-CH2 -Cl
71. what is the major product obtained in the following reacrion ?
Et'o
+ cH3
- Br , Product.
Gt*"
,"rO orftn'
CHq
---r s
"r',2 >A; The productA is :
+ oH-

')3:"
H

(a) (b) ,:>o(:"

(c) Both (a) and (b) are correcr (d) None is correct

73. Me2C = CH - CHz - CHz - Ct ='11 ,

CaCO3
(X); Major product of the reaction is :

OH
I

(a) Me-C-CHz-CH2-CH2 (b) Me2C = CH - CHz - CHz - OH

I

Me
OH
(c) Me2C : CH - CH- CH2 - OH (d)>l*.,
OH

HBr , (A) (5'-on n,',,r,

Y
74. ,
A \

cH2oH
cH2oH ocH3
Product (A) and (B) respectively are :

r"'qo" and G)q"" and

CH2Br Br CH2Br OH
ii,
liili:li,f,,',lii,:i;.,:*iilii

,.,q"'and
CH2Br OH cH2oH ocH3

75. Relative rate of reaction with HzO.

/o
I

[-oNS---o-[-O^.",]
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii)
(c) (iii) > (ii)> (i) (d) (iii) > (i) > (ii)

oo KNHz n-c+Ho-Br ,
76. ll ll 2 eq'
, 1P, '
NH3(l)

+1
t \.,A.. then H3oo

End product (P) of the above reaction is

oo
:
oo
(a) (b)
_J
AA
-]
I

oo oo
AA AA
77.
(c)

I (d)

-i
Which of the following statements is correct regarding the rate of hydrolysis of the
compounds (A) and (B) byS*r reaction ?

I FBr O,F. FBr

v A
\-/
B
 (a) A reacts faster than B (b) B reacts faster than A
(c) Both A and B reacts at the same rate (d) Neither A nor B reacts
78. What are reactant X and product Y in the following sequence of reactions ?

o
il
- -+ "'#r".r
Reacta
o
Bridine f M/- H Product Y

Reactant X Product Y

ta)
H, H3c:/.,\ \/-\/rN3
H"." LJ
-H

"'[M>/"7

(c)..:\-/:_ ,,|\o/"7
(d) '':Se/; ',1\O/),
79. Transition state of given S1,r, is :

QI #(!)I:
.z\zCHz-B' n n- .--zCHz-o-R

6e 3 (+)
9R OR
lrr
(a) :..N ;. (b) /-\ : ..,...s "
\_/\*,
:

Br
1 6 (+)
 6 (_)

9R
(c) (d) ,F\, ,.s'
\_/H
:
Br
6 (-)

80. CoHrsBr + OH- ---+ C6H13OH + Br-is an example of:

(a) Nucleophilic addition (b) Nucleophilic substitution
(c) Electrophilic addition (d) Electrophilic substitution
(e) Free radical substitution
81. Transition state 2 is structurally most likely as :

(a) intermediate 1 (b) transition state 3

(c) intermediate 2 (d) product

,,4

x = Number of aromatic compound obtained when above compound undergo complete

acidic hydrolysis.
(a) 1 (b) z (c) 3 (d) +
Sp 1 and Sp 2 reactions are
(q) Both stereospecific
(b) Both stereoselecrive
(c) Stereoselective and stereospecific respectively
(d) Stereospecific and srereoselective respectively
 {srrrs .rffii.,,
84. Most reactive compound toward Srr is :

,,,d ,,d (c,/{'-',.,,d

1. (a) 2, (b) 3. (c) 4. (a) lr. (b) 6. (b) 7, (b) 8. (d)

9. (b) 10. (a) 11. (c) a2. (a) 13. (d) 14" (d) 18. (b) 16. (c)

47. (a) 18. (a) lg. (c) 2(J. (d) 21. (b) 22. (a) Zg,i,. (c) 24. (c)

25. (d) 26. (d) 27. (d) 28. (a) 29. (a) 30, (d) 31. (b) s2. (d)
33. (d) 3,4. (c) 35. A(a) 35. B(b) 36. (d) i37. (b) 38. (d) 39. (b)

4(J. (d) 41, (d) 42, (a) 43. (c) M. (b) 45. (c) 46. (d) 47, (a)

48. (b) 49. (b) 50. (d) 51. (b) 52. (d) 53, (a) 54. (b) ttb. (a)

56. (a) 57. (b) 58, (c) 59. (c) 60. (b) 61. (c) 62. (d) 63. (a)

64. (b) 65. (c) 66. (c) 67. (d) 68. (c) 69. (d) 7o. (c) 71. (c)

72. (b) 7$, (d) 74. (b) 75." (c) 76. (d) 77. (b) 78. (b) 79. (d)
80. (b) 81. (c) 82. (b) 83, (c) 84. (d)
*ifi*.

1. Statement-L : Nucleophiliciry order in polar-protic solvent is I- < Br- < Cl- < F-
Statement-2 : Due to bigger size of I- it is less solvated in polar-protic solvent.
(a) Statement-l is true, statement-2 is true and statement-2 is correct explanation for
statement-1.
(b) Statement-l is true, statement-2 is true and statement-2 is NOT the correct explanation
for statement-1.
(c) Statement-1 is true, statement-2 is false.
(d) Statement-l is false, statement-2 is true.

2. Statement- L :CH3 -CHz -Cl+5u1 Acetone ,CHs -CHz -I+NaCIJ

Statement- 2 : Acetone is polar-protic solvent and solubility order of sodium halides
decreases dramatically in order NaI > NaBr > NaCl. The last being virtually insoluble in this
solvent and a 1o and 2o chloro alkane in acetone is completely driven to the side of
Iodoalkane by the precipitation reaction.
(a) Statement-1 is true, Statement-2 is tme and Statement-2 is correct explanation for
statement-1.
(b) Statement-1 is true, Statement-2 is true and Statement-2 is Not the correct explanation
for statement-1.
(c) Statement-l is true, Statement-2 is false.
(d) Statement-1 is false, Statement-2 is true.
3. Encircle whichever of the following :
(a) is the stronger nucleophile (aprotic solvent) : F- or I-
(b) is the stronger nucleophile (protic solvent) : F- or I-
(c) is the stronger base : F-or I-
(d) is the stronger nucleophile (protic solvent) : NH, or NH2NH2
(e) is the better lear.ing group : CH3COO or CH3SOj
4. Encircle-whichever of the follorving
' ,,
I

(a) undergoes an Snz reaction more rapidly, CHe - Br or CHs -CH-CH3

Br
(b) undergoes an S*r reaction more rapidly, CHs - Br or CHg -CH-CH3
I

Ph.. -,Ph
(c) undergoes an E2 reaction to give (z)-7,2-diphenylpropene , : clcg,
*,)a
Ph Ph
H-le.
lor
H
H-]-cH3 cHs
Ph
 .f.#### .,.,,.,;,...,,iu,r10 *,,.,.",1,,..,;,r:,, .r, i,r.jr , E$$
(d) reacts with NaI to give (Z)-1,2-diphenylpropene :

Ph Ph
H*Br I
sr--l-FI
lor
Br-'l-cH3 n'-fcH,
Ph Ph
(e) undergoes an S*r reaction more rapidly,

Br Br

w
D. Encircle whichever of the

^o.ro.
following
(a) undergoes an S*z reaction more rapidly ' </
r1-cH.-Br z'
or OK::'
fn, j':_

(b)undergoeSanE,reactionmorerapidlyry.,-.,,_[T,",,ry.dI-.,,
\2
(c) undergoes an S,r r€oction more rapidly:
t'Do'r.0

(d) undergoes an S *z reaction more rapidly:

A
(e) undergoes an E2 reaction more rapidly :

A orfu.,
 :i ffiffil.

Rblatfue,rate Relnd+b rate

:,htltde '1gt I.
,,.'.' ' ,

{ffi CH3 - Br {#n 1 .(ffi 1200

i'ffiI CH3 -CHz-Bt {$ 1.05 ffitr 4A

CHs *f;H Br
(cI .H,.} 11 f#I T6
CH:

cHs

ffi} cHs *t * nr
I
($I 1,200000 ffi,I 1

cHs

Matrix :
 (a) undergoes an S*z re&ction more rapidly, o,
h-8, O(
(b) undergoes an S*r re?ction more rapidly, (CHg )3C - Br or (CHs )rC - I

(c) undersoes an s*r reoction more rapidly, or

fu"t d}
9. Reactivity : Circle the reaction that reacts FASTER by S*z in each pair :

(f)*C1 NaocHg
r(Z)*I H^o > (3) r-l ___+
lvr NaOH

g, NaOCH:
, , NaOH
, \, Cl NuoH_>

10. Consider the potential energy diagram given below

>1
00
c/
r*1

Retttion Frogr€ss

(X) Name the positions A-D

(Y) Answer the following questions .
(i) Both reaction pathways are : D(OTHERMIC or ENDOTHERMIC
(ii) Which step is the rate determining step (ROS) ? B orD
(iii) Which product is most stable ? E orF
(iv) In accordance with Hammonds postulate, exothermic reactions tend to have
(a) early transition states that are reactant - like
(b) late transition states that are reactant-like
(c) early transition states that are product-like
(d) late transition states that are product-Iike.
l::lir:+iiri: lilil(iii i:ii ia:itji,i: iN::: at:j il::::j i t::: i: I I il: iir, i i:ti iti iit:.ri.i i ri,i::arrji

, ,'t',..',1 ,, t,, ,,,,,, ,,,,,, ,'

'Stfit,.;,.

L L. Select whether the following combinations of reactants will react by substitution (S

*r or S
*z
mechanism), elimination (E1 or E2 mechanism)

A. }r, *,;*:*_,

(a) S
*r @) S
*z (c) E1 (d) Ez

B. tffia, NaocHs inmerhanol

\r' so"c

(a) S (b) S (c) (d) Ez

*r nz E1

NaOCH3 in metlranol
25'C

(a) S*r ft) S*z (c) Ei (d) E2

D. (CHs )s C - OH ^'"' 48olo

HBr ';_, in H"O
;' "'" )
250C

(a) S (b) S *: (c) (d) P,

*r E1

NaCliincthanol
E. (CHs )2CH - Br 25'C

(a) S*r $) Sr: (c) E1 (d) Ez

F
(a) S*r
F" r{ry in ethanol

(b) S*z (c) E1 (d) Ez

G. (CHe )zCHCH2CH2 *OH - HBr 48olo in H2O

(a) S*r (b) Srz (c) E1 (d) E2

 1- 1'j1..:::ir. i .j.i:i:l:r.:lll.if:jili;;c.::1+:1.
..t .. :,-r, .....

Examine the ten stmctural formulas shown in fig. & select that satisfy each of the foliowing
conditions. Write one or more (a through j) in each answer box.

cHg
I
CHz BT
HsC-9-Cl
I

cHs C
rycH2-Br
cHs
cl
H:C-C-CH2-Cl
I -
"t\arcH2I
I

cFI3 cHs

A. Which compounds give an S^,: substitution reaction on treatment with alcoholic NaSH ?

B. Which compounds give an E2 elimination reaction on treatment with alcoholic KOH ?

C. Which compounds do not react under either of the previous reaction conditions ?
reactlon palrs wlll occur taster.

H,O
DMSO

CI I
cHs .,I*I , l cHs
DMSO

CHiCI
NaI
DMSO

I C1

11 Nacl H
,
DMSO

NaCl
---+
EtOH

I N3
H NaN, , H
DMSO

Br N3
H NaNs H
)
DMSO
'xoq ua^It alrl q ra^asut rno{ {DII 'vl
 Bromocyclohexane

iffi

riiiiiiii.irii
iiii il I lir, ., I

ffi.. Bromobenzene

:::i:::: i:': .',i.N

:.::i:i:: ! :r'

CH2- Br ,H#
ffii
o
I
iii;rl =tir
Benzyl bromide
.
,i

1-Bromo-2,2-dimethyl
propane

Y g......:..i ..i

Bicyclo compound
iffi
1:l.,,..,,. No

Yes

1-bromotriprycene

No
; ili:;i:i iil::I:r ii a*ila| i 1::i i: !ii!i

L5. Match the column

16.

€("rex"_" xHr,

How many (x) moles of HI consumed?

 (*€effiot cequence)

Y.u__* low

\ \r_ _-____?
OEt
v_
-/ EtOlVH0

ffil Et-cr--"-* /\/ Et-CVNa ether

.li i ,,i
ti,'1
;.'riiii.,i.i,iiiii;i,i1iiiriiii11 .':l

1,9. Choose the one compound

The compound that reacts with alcoholic

KOH to liberate Halide ion through €VF
substitution reaction. OrN/#
'l
cHe

The compound that cannot be prepared by

a Williamson ether synthesis.
G"czHs
The compound that gives an acidic solution
when allowed to stand in aqueous ethanol.

The ether that cleaves more rapidly in HI. ( t G+-cHs

 i1li..r "i.' :1.., tlr.l j

,,t.. .
:'
,ti, : t
H

1. d
2. c The reaction is Finkelstein reaction.

3. (u)@;eu)O;(c)@,,0,@; (e)@
Br
4. (a) CH, - Br (b) cH3 -cH-cHs
I
Br
(c)
cHs

Br

(d)
H
Br
Br
cHs (e)oO
!H

s' t"'#cH2-Br .o,ry'tl'-'"' (c)t'I>

6.
(d)
A
z-p,w;b-g,X,c -r,Y;d-s,z
,.,fu.,
7. a-t,s;b-p,Ql c- r,s:d-r,s

8' tu
hr.
(b) (cHs)'c-l

9. (1) *s, (2) \,.AI (sl\Act

10. (X) A- reactants, B-transition state, C-lnter mediate, D- transition state
(Y) (i) exothermic (ii) B (iii) F (iv) a
11. A-b; B -b; C-d; D-a; E-b; F-b; G-b
12. A- C, d, e, f, h; B-b,c,f, i;C- a,E, j
13. Part- 7 2 3 4 5

Reaction-ADEG I
14. Yes - a, b, c, d, f, h,
No- e, E, i, j, k
15. 3-p, e, r, s, t; b-p,s,t; c-p, e, r t; d-p
16. 2
17. o-p,ri b-qt c-s; d-r
18. a-q; b-p; c-r; d-q
19. u-p; b-r; c-s; d-q
 Eliminatio#' ffiilI'ffiHii

1. Which of the following alinl halide gives only one product (excluding stereoisomer) when
undergo E2 reaction ?

(E z : elimination bi-molecular)

CI

(d)

+
CI

2. zAt.,.A-.
I E, reaction
,
,.Hoifmann product)
+ ./v\
(Saytzeff product)

(A)In the above reaction, maximum Saytzeff product will obtained when :
(a) X=-I (b) X=-Cl (c) X = -Br (d) x=-F
(B) In the above reaction Hoffmann product is major when X is :
(a)' -I (b) - Ct (c) -Br (d) -F
B. 6l-H(P)
\-,/
when (P) undergoes Hoffmann exhaustive merhvlation (rwice) then the product obtained
r,r'ill be :

c^l fi'o) ror (*) (c)l- (d)l^

o-
I ?'
4, I
\Apr,
I
--Ei--+(A),
Ei e8o/o aY\\re
r -E-(B),
Er
on s5o:
(syn) X

o.-.,,o.-,^
(P) (Q)

Product (A) & (B) of the above reaction is :

(a)A=P,B=P G)a=Q,B=Q (c)A=P,B=Q (d)a=Q,B=P

ACH' HO-
Major product of the reaction is :
..4
'rt//
OTs

,"rry (b)u nry (d)eI-

Which of these dehydrates most easily ?

(a) CHs
-CHz -CHz -OH orC/'[i,
cHs

r.rloH (d) cH3

I

-! -.nz -oH
cHs

NaOCH"
Product; Product of the reaction is :
cH.oH
--+
(82 reaction)

(d) No reaction
ocH3
 NMe:
- Ho-
8.
- I l+A A
\-/ (Major)

Major product A is :

,rrd ,rr0 ,.rd ,.r$

H2SO4
9. + A
A
(Major)
Major product A is

G)aY),r@ (d)re
:

(,)OO
10. In which of the following reaction Saytzeff alkene is major product ?

!n'.
(a) cH: -cHz-[*ir., + O) cH3 -cHz -cHz *r, --Ef----+
f
(c) cHs -cHz
f',?' a
J
{ -cH3 r-BgoK
> r
(d) cH3 -cHz -cHz-Q cH3oK
' "fr,-cHg" a
>

f,
CH"
r'
Ph-+- H atc. KoH
+
11.
ph-1- I gr (E, reaction)
Major product of the reaction is :

cHa
Ph
-.
Ph
t ,ZCHI ,/Ph
(a) : C_. (b) : C-.
_c
- -cHg -C
cf,, -cHs
Ph
tn'a. Ph_CH_CH_Ph
,/Ph
(c) c-cH, (d)ll
Phtc: cHs oH
12. The conversion of 2, 3-dibromobutane to 2-butene with Zn is :
(a) Redox reaction (b) cr-Elimination
(c) B-Elimination (d) Both cr-elimination and redox reaction
13. 1, 3-Dibromopropane is heated with zinc dust in ether. The product formed is :
(a) propene (b) propane
(c) cyclopropane (d) 3-bromopropane
o

14. Reaction (1) alc' KoH , (A) (major)

ry"
?
Reaction (2) alc' KoH , (B) (major)
Qr.
o

Reaction (3) arc' KoH , (c) (major)

+Br
Product obtained in above reactions (1), (2) & (3) is :

(a) A - B but C is different

(b) A = C, but B is different
(c) B : C, but A is different
(d) A : B : C all product are identical

CI

15. Reaction (1) Cl

3 mole alc. KOH
(A)

CI

C1

CI

3 mole alc. KOH

Reaction (2) CI
(B)

C1 -.\\Cl
,rrttCl 3 mole alc. KOH
Reaction (3) C1

Product obtained in above reactions (1), (2) & (3) is :

(a) A =B,C isdifferent (b) A : C,B is different

(c) B = C,A is different (d)a:B:Cissame
#ffi qi*ffih r#r#ffi
L6. (x)
x is number of E2 product obtained
Br (including stereoisomers)

Find (x).

(a) 3 (b) + (c) s (d) 6

cHs
I

17. cHe
-9-tt cH-cH3 -ff!+(a)
CH3 Br
Major product (A) is :

@xz o) >< rctX. (d)><

L8. Which one of the following compound will be least susceptible to elimination of hydrogen
bromide ?
(a) Br CHz CHz NOz (b) gr CHz CHz CH:
(c) Br - CHz - CH2 - CN (d) gr - CHz - CHz - COrEt
19. - - - - when
Two alkenes, X(91% yield) andy(9o/o yield) are formed - thJfoilowirg.o*pound
- is
heated.
cHs
@
N(CH3)3OH 9lo/o 9o/o

The structures of X and Y, respectively are :

(")O-cH3and *,ftcH3and
O-.n, ry.r,
(.)*cH2and (d)ftcH3and
20,
ry.",
In the dehydrohalogenation of 2-bromobutane; which conformation leads to the formation
OF.n,
of cr-2-butene ?

?', cHs

,,,]ff',0,)k." (c,H (d)

cHs

H
HH cHg

o-H o
il
CHs-C-Cl(2mole)
27. Pyridine
(a) (Ei)
o+ 1r1 + cH3co2H

o-H
 Product (B) of given reaction is:

"ro o)o .,0 .,,0

22. What product will be formed from Hoffrnann exhaustive methylation of following compound?
(i) CHs-l (excess)
Me2CHCH2NHCH2CHzMe
Ur*;--+Product
(iii)
A

(a) Me-CH:CHz (b) H2C : CHz

(c) CHs
"l- C :CHz (d) CH3 CH CH : CHz
- I
-
cHs Me
cH2- oH

2s. a t{--

-ital
3

Product (A) is:

(")a *,o ,.rO (d)o

CHo
Y"
24.
>. -F1products
O
OH
obtained are :

(a) Racemic (b) Diastereomers (c) G.I (d) Positional isomers

*',91,t
zs. $= (Ezreaction) . , ; Major product of the reaction is :

V"rc,
=
,4t.

+
(a) (b) (c) (d)

Q Q {
 r product of the reaction is :

,.r# (d)

27. The E2 product of the following reaction will be ?

Q
cHs
NaOH

(b)

(c) cHs
,,
G)m*u
28. An halide CsHrrBr on treatment with alc. KOH give 2-pentene only. The halide will be :

(a) CHs -CHz -CHz -CHz -CH, - Br (b) cHg -cHz -cHz -cH-cH3
-l
CHs Br
I

-l
(c) CH3 -CHz -CH-CH2 -CH3 (d) cH3 -cH -g -cHs
I

Br Br
29. End product (D) in the given sequence is:
cH3I
(2morarequivarenor(c) As2olH2o>(D)
r,Gr.
\,/ r;#ffi*;1(A)--Ee566y + (cH3 )3 N

(a) o

*ro ,r+ ,.r#

+ o OH
gO. For each of the following pairs of E 2reaction, select the one that occurs with the greater rate
constant.
cHs cHs I

I I

(1) CH3CH2CH2CI+CH3 - C- O- (2) CH3CH2CH2I+CH, - C- O-

cHs cHe

(3) H3C -CH -CHs +CHrO- (4) HsC -CH-CH3 + CH3S-

I I

Br Br

(')On.a + -oH' (6) + -oH

(a) 2,4,6 (b) 1, 3, 5

(c) 2,3,5 (d) 2, 4, 5
Br Br
I l- xNaNH2 y cH3l
31. CH3-C CH3--{:C-C:C-CH,
It
Br
-C -CHs
Br
-
x and y mole consumed.
Valueofx+y:
(a) s (b) 6 (c) 7 (d) B
3.2. The following bimolecular elimination reaction (Ez) is carried out with different halogen
leaving groups. The per cent yield of the two products (2-hexene and 1-hexene) for each
leaving group is listed below.
X
.L--. -/ + CH3O-
Leaving group Conj. Acid pK, %-yield of 2-hexene %-yield of 1-hexene
X:I -10 Blo/o 19o/o

X:Br -9 72o/o 2$o/o

X: CI -7 67o/o 330/o

X=F 3.2 3Oo/o 7Oo/o

\rVhich of the following statement is (are) true concerning this series of E 2 reactions ?

(a) Based on the pKu'S of the conjugate acid, I- is the best leaving group and F- is the
poorest leaving Sroup
(b) When I-, Br- and Cl- are used as leaving groups, Zaitsev's rule is followed
(c) F- is the strongest base (and therefore the poorest leaving group) and the transition
state for reactionwith fluoride as the leaving group has the least double bond character
(d) a, b, c are true
 , (1)q4
)J ^N(Ctrl";,
6ntro
LL,
A
(3)
33.

D
[;] fd B

Product (A) & (B) respectively are :

,.,4r: &
ar: ",5a, ar:
,.,5( ari & ,.,4f: ar:
34. 611 conc Hzso+,
,^, [li#*' , rrl 1ffi] (3) A
rcl

Product in above reaction is :

,rrO *,o (c) ,o,o

35. Major product obtained in the reaction of 1-phenyl-2-bromobutane with NaOMe is :

(a) (E)-1-phenylbut-1-ene (b) (E)-1-phenylbut-2-ene

(c) 1-phenyl-2-ethoxybutane (d) (Z)-1-phenylbut-2-ene

36. Which of the following alkyl halides give most complex mixture of alkene in anE, reaction ?

(a) CHg -CHz -CHz -CH2 -Br (b) cHs -cHz -cHz -cH-cH3
Br
cHs
I

(c) CHs -cH, -cH-cHz -cHs (d) CHS _C _CH2 _CH3

'l
Br I

Br

,rrr|34li,
37. ml] arc' KoH , (A)
[H (major)
\./
P{oduct (A) is :
 (")fFl o) ,ors'
Yo,
Bs'
ry"'+*(A); O {--co
Sum of number of cr-hydrogen present is compound A + B is :
(a) 18 (b) 1e (c) 20 (d) 21

g9. q4; (1) excess cHsr/xrco,

,,r.,
7\u)ff[l],"ilr'3t'3l/K2co3 H2C = CH-fH -CH = CHz
(2)Ag2o/H2o
(3) cHs
^
Identify A :

,",ff
\*/
G)

H
Br

cHs-cHz-c-cHz-r,
I
alc'KoH
40. , (A)
(major)
|
CH2(n - pr)
n-Pr=n-propyl
Product (A) is :

Me Et Me Et Me Et Me
(a)? ,o)l (c)v (d)?
Et

X
I

PTT HPr Pr Pr

Ph
I

41. (\on , Major product obtained by dehydration of given alcohol is

\,,,4.. "ioo :
 Ph

,.rd
xv NaOCHq (2mole)
41 Haoo
42. cH3oH
> 181

oH
Product (B) of above reaction is :

?' i'
,^,e(oo"*,,,d ,.,docH3,o,do,
43. Ph
- !H- cHz - fr, -4p Product
Br Br
Product of the above reaction is :

(a) Ph-CH:CH-CHz-Br (b) pr'{

(c) PH CHBr CH : CHz (d) Ph-C:C-CH3
- -

44.
ffo,
V -."" 'r* ,,o,
I
OH

G)l'il ,.,6
Product (A) is :

(.,+
H

NaOEt
45. -_--------,
PhA
NMe3
@

Major product of the above reaction is :

 Ph .\. Ph\6:
(a) t-./Ph G)
ph/ -
,-'n
-\
Ph/c: on M"

M.\ .zM'
\ph
(d) t-or,
Me Ph/c:

46.M ---
LDA
> A* Nz + ph-CH:CHz,productAis:

N
\NH-cHz-cHz-Ph

M
LDA : Lithium di-isopropyl amide

M
(a) (b)

,.rM (d)

\_*_l
47.
or
Major product of the reaction, when the given compound undergoes Hoffmann exhaustive
methylation is :

\
(a) .,ro ,ro (d) H2C : CHz

cHs

48. -+=P -- Major

Pyridine r product of the reaction is :

(a)
arre
 ,ro
Ph
lt
Ph

C: CH-C-OH

'*A , Product

Stereochemistry of the product is :

(a) Meso compound (b) Racemic mixture

(c) Diastereomer (d) Optically pure enantiomers

Which of the following reactant is used to obtain above compound (A). (Assume that EtO- is
used in all the reaction)
Br CH 3
H
=-./,
tBr
(a) oo) o (c) o (d)

H
sr.. (Cq\ arc. KoH
,(A), productA is:

HH
OH

(a) c)o" (c)

52. Rank the following in order of decreasing rate in an E2 reaction:

cHs

-'"'
ar'cH3
nr
\-'J<
Y,,,,,cHs
(a) (b) (c)
(a) a>b>c (b) c>a >b (c) c>b>a (d)b>a>c
sB. Pha I
KoH
EtOH,A
> (A) , Product (A) is
(major)
F

@tpnN G)pnA/ (c) ph/Y @)PIra

OEt OH

s4. a -S(A)Major
Br

INMegiS A
(B)Major
@
Relation between (A) and (B) is :

(a) G.I. (b) Positional isomer

(c) Enantiomer (d) Chain isomer

3NaNH2
55. Product ; The Product is :
Iiq.NH3

(b) HC:C-(CHz)3ONa

(c) NaC:C-(CH2)3ONa (d) H-C:C-(CH2)3OH

56. Which best describes the product of the following reaction ?

CH"

,r4'for-(d%Product
(a) Absolute configuration has been inverted
(b) Absolute configuration has been retained
(c) Racemization (loss of absolute configuration) has occurred
(d) Loss of chirality has occurred (the product is achiral)
57. What is the major product of the following reaction ?

CH"-CH"-C-CH
rzl\a
?' /"' n* ,product
cHs CHg
lffi
cHs

4,r.. I

_ cHs
/cH - cH3 /cH
(a) cr (b) "t/C: Ct
n": cHs cHs tH,
cHs

n.\
I
cH3
,cH - cH, \ lcHs
(c) ttanran, (d) ca.r,
n/': cHscH/c:

58. What will be the major product of each of the two reaction shown below ?
heat
" 'l
1. CH?CH?CHCH3
I
+N(cH3)g-oH l-r CH*CH:CHCH3+CH3CH2CH:CHz
- 'l
2. CH?CH?CHCH3+ CHTCH2ONa
heat
, l"xY
Br
(a) 1-X,2-X (b) 1-Y,2-X (c) 1-X,2-Y (d) 1 -Y,2 -Y
NHCH2CH?

59. + cH3I (excess) -----) product; The product is :

(a) a primary amine (b) a tertiary amine

(c) a secondary amine (d) a quaternary ammonium salt
cH2-oH
60. n* ,ta1---luslrle513;
A

(A) on heating isomerizes to (B). What is the structure of (B) ?

,,,0 6
OH

H
I
.o, ,.r0 (d)
6
Ph-C-Ph
cHz-cH2-oH
61. '*A , (major)
(A) , major product (A) is :
 .,i:: : iii 't.,., ... la , . , :.:

i
nt,,t. i,

fi0;ffifiiifi#

cH2-cH3
(b)

cH-cH2 cH2-cH3
(c)

62. Which of the following carbocation will undergo rearrangement ?

L e
(c) CHg-QH-C = O (d) cH3-NH-CH-CH-CHs
I I

cHs cHs

63. In which of the following reaction resonance stabilized product will form ?

cH2-oH .A..-oH
(a) -- H*
^----'
(b)
t, -+-,
H* (d) All of these
(c)
-A*

64. In which of following reaction rearrangement take place with change in carbon skeleton ?

QHs
161
(a) cHc-c-t'H, (b) cH3 -cH2cH2@
"l
cHs

(c) CHg - qH - cH, - 8u, (d) cH3 -cH@ -cH:

I

cHs
 f,;,,',,,, .,.,,',,,, ' , :',,. '
. ,ffItc #ft,
Consider the following reaction :

,OH
Which response contains all the correct statement about this process ?
(1) Dehydration (2) Ezmechanism
(3) Carbon skeleton migration (4) Most stable aikene will form
(5) Single-step reaction
(a) 1,3 (b) 1, 2, 3 (c) I,2,5 (d) t ,3, 4

H Br
66' H oF{ --J1EL--> (x) ;+:1--+ (r') (Major); Product ()') is:

CH:
(a) cls-2-butene (b) trq.ns-2-butene
(c) 1-butene (d) Iso-butene
Br Br
ti
6'7. CHz-CH : (dust)
+(A)
-g11" --!'
CH

Above reaction is an erample of 1,4-elimination. Predict the product.

(a) CH3 --CH:C:CH: (b) CHs == C --- Cf{?
(c) CHr-CHz-C:CFI (d) H2C -C
: CI{ __ CH :- CHz

Ph
68. --!9nc'llzso+--+ Major product of the reaction is:
OH

,rr@
(d) None of these
AIJfYL ITATTT'g$
Ph CHs Ph Et
llllr
69. Ph-c-c-CHs+ph-C-c-e, H2so4
>

tl
OH OH OH
ll OH
(A) (B)

PhO Pho
(p)
til
Ph-C-C-CH3 (q)
ril
ptr- C-C-Et
I I

cHs Et

PhO Pho
lil
(r) Ph-C-C-CHs (s)
lil
Ph-c-c-Et
I I

Et cHs
When (A) and (B) reacts with H2SO4 products obtained are :

(a) p, g, r, S (b) p, q (c) p, q, r (d) p, q, s

70. Which of the following compound gives even number of Hoffmann's exhaustive methylation
and elimination?

,"rQ (b) (')eT) (d) ^N{

I

.A,-:il-.n"J1
Tr. \rt[L;. \-] arc'KoH
, X=Numberof chirarproducts
" (including stereoisomer).
A
9cHs
(a) 2 (b) 4 (c) 6 (d) 8
$1S Oft$ i,ryemf,#E : rf*. l*.IHfr

1.

.9:-
!.7.
qI,
g3i
tl:
f?.
57.
70. | (a,b) l7L.
 $I'7,

E2 reaction -) Elimination bimolecular

In the general mechanism of the E 2 reaction a strong base abstract a proton on a carbon
atom adjacent to the one of the leaving group. As the base absuacts a proton, a double bond
forms and the leaving group leaves.
->-=a -CHg
H..
vrrz
vrr3-CHr
CHq -CH-cu"-**=*
vrr3 cHrou 'cH{ \H '' +/V
T'^ "
Br (major)
Mechanism :
-+
-^r, i-- f."i8
| 1l
i l+
--u^(-
cHrbNa + CHe-CH-CH-CH,+ |tn,-CH"""
vrr
9I- -cH I

I sP"
I

-11
BrlLDtl I

'1,:;ffi.'Jxffi,l'i'"
I

->
(ronr-z-autene)

A. Identify the rate of reaction of given compounds in E2 reaction:

Br CIF

(a)a>b>c>d
oa(b)
(b)a>c>b>d
(c)
(c) b>o.>c>d (d)b>d>a>c
B. In given pairs, which compound is more reactive toward E, reaction:

0r)
(a) CHs - qH - CH3 cHs-qH-cD3
I I

Br Br
(III) (rv)
 (R)O Mcvl) U*
(s) Ph-cH2-cH2-Br Ph
-
il;Xr,
(a) P-II,Q-III, R-VI ,S-VII (b) p-II ,e-III,R-VI , S-VI
(c) P-I, Q-III , R-VI , S-VII (d) p-I, e-II , R-V, S-VIII
Ph Ph
I

c' :X+[ -4'QE-(A), $1,

acroH >(B)

Ph Ph
Product (A) and (B) are :
(a)A:cis,B:crs (b)A:trans,B:crs
(c)^4_:trans,B:trans (d)A-cls, B:trans

D.&,*tr-tar, &,-yl-c,
_!
,4. A.
Select the products (A) and (B) from the compounds (P) and (Q) given below:

fr,,
a-
\i :
q
(O)
(P)
(a)A:P,B:P (b)A:Q,B:Q(c)A:Q,B:p (d)A:p,B:e
E. which of the following compound is inert toward E, reaction.
-Br

o)o
(a)

'
CHs -
Br
fH
cLH
- CH2 - CH3

i"
(c). cHr
- i_ .rr - Br (d) cH3
- f- cH cH3
-
CHg CH3 Br
AIt;r<YI;,
:li;;til:;*ti:,:::i:iii

[Er,5J?IrNAruAN] ilfxil#.ii

2. Match the column :

rgacti$fil, , ,,,,,,
'Ez ,,, **i'A ,pil$tffi[A$,r.odu iii
(ellmination bimolecular) (inctuding stereoisomerisrrl)

,
1
(a) alc. KOH
I

T
A
1

alc. KOH
i
i rb) A
i
Br
i

.,
I
I

(c) .*Br
-,lt'xqE--+
A

I
I
i
1

i....:
(d) *rr -4sKel-- lo,
Match the Column :
HEM : Hoffmann exhaustive methylation followed by elimination.

: *
(J--uEu.-) H2C CH
-
CH2
-CH
CHZ

I
H

(I HEM
> -HW,
H2C : CH-CH2 : CHz
-CHZ-CH

HEM+ HEM
- ---------+ 9H,
ta) :
I

:
H2C CH CH2 CHz
- -C

A HEM
(d) L
-N/ )------,
HEM

{s}
H2C : CH-
cHg
t"
CH CHZ
I -CH:
H
Match ttre column :
: uurnloD erp qrleill 'L

: urunlo, eql qrltiltr

9. (a)ry -+ft {fiproducts
Br
Br
alc.KOH
&) I , 1r1
, -/A-
(c)
,^Y^- alc.KOH t^
I -_:___* l4)
Br
10. Reaction-l :Ph-C -CHg Pcls > ElwaNHr, cHsI )ph-C=C-C;s
Br

Reaction- z, +ry.:euj ;c =c -cH3

I
Br
Reaction-3 : ph
^-/- cH - cH, ENaNH2 ) Et-I >Ph
- C=C - Et
l14
CI CI
x, !, z are moles used.
Sumof Ix+y+z- ]
11. Sum of cr-hydrogen in major product of the reaction.

-oH
t

r./-\ \.I
Reaction-L l I 4- r(A)
.r+

Reaction-2

Reaction-3
H- ) (c)
A

Rbeffion,4 (pi
: ,,tt r, ,, :':

Surnof a-hydrogenis A+ B * C * D:

tt*

12. Reaction-1 '] > (e)

' ' ,&'
1,.',

$Hg ' '

Reacfion-2
I
CHr-- CH,,*CH2.- CHa- OH , ':F1,; > 1B;
A
CH"
CH:-- I "
Reaction.S
cHg-
;cH- cH * cH2 - oH t.
A
, (c)

Sum of o-hydrogen is (A * B* C:
irliili;il!.li iliri iili:iii

g+
L3. Reaction-L (A)
a (majsr)

Reaction-2
G*--,J#];
H*
Reaction-3 -.-------------' (c)
oHn' (major)

Sum of o-hydrogen (A + B + C) :

.
14. (a)
\r/

OH
I
H*
------+
A
(x) G)>(
'oH^
H- > (y)

tt' -.,
OH
l-. -= @) (d) >-<
oH^ '*
, (p)
Total number of products obtained in above reactions including minor products is (including
stereoisomer)
@@

15. Match the column (I) and (II).

. .ilr. -,. :,. . r.,

*efi
.

Ilpq,,of i;x;.iii.l,.,

R -2 -chlorobutane KSH >

acetone

o
R - 2- chlorobutane
x1--)
-E!-o-
EtOH

,
2 - bromo- 2- methyl propane
H"O
>
-^'2"
 Igfr *ffifr

Match the column (I) and (II).

ffi 1Ae u*ur,tl

(p) sNt
*,* ao.KOH

ffi alc.KOH
IH SN,

(c) (r) El
H.O

(d) H* (s) E2
--:---:-+
A

1.Z. Select whether the following reagent combination will result in elimination or substitution
reactions leading to the major product.
Match the Column and (II) (Matrix).
 Major product consist of o{d
ii##ilii
H*
ffi number of o-hydrogen
A

1.9. For each of the following amines (A through D), exhaustive methylation (treatrnent with
excess methyl iodide), followed by Hoffmann elimination (heating with AgOH), repeated as
necessary, removes the nitrogen atom in the form of trimethylamine. Indicate the number of
repetitive Hoffmann eliminations required to remove the nitrogen by a number (1 to 4) in
the desisnated answer sheet.

ilililiii
b.
liri ii
:::it: l
,ffi ItLt..

,.'s1 ,:.
G. f;
2().

ive Methylation and

elimination*s) to'remsve nitrogen from given compound.

alc'KoH
,y is total number of possible E2 product (including stereoisomer)

Surn ofi*+;r= P

21.
CH"
l"
cHfiH1--€H{H3 ,iill
Br "'-" ) (x) ,,
($u$r + E1) products. ( including stereoisomer)
consider all products

Total number of pr.oducts ar€,1

 1. A-a; B-a; C-b; D-c; E-c;
2. a-s;b--r;.-q;d-p
3. a-s;b-r; c-q;d-p
4. ,-p, q, s; b-p, ri .-q, s; d-r
5. u- p, r; b-p, ri C -p,ri d- q, t
6. a-p;b-r; c-q;d-s
7. a-p;b-q;c-s;d-r
8. a-p;b-q,c-r;d-s
9. X:3, y =3, Z :ZP=0= 3+3+2+0=B
L0. x=3, !=Zz=3 +3+2+3=8
LL. 32
12. 33
13. 28
14. x--3, !:7, z=3,P=2
Sum=9
L5. (a - q), (b - s), (c - p), (d - r)
L6. (a - q), (b - s), (c - p), (d - r)
17. - d, f
Substitution
Elimination - a, b, c, e
18. a*p,gi b-p,eic-q;d-r
19. a-3;b-2; c-3;d-1; e-2;f-3
20. 6
21. 6
 E$
*- r,.,

r 1' one eq' NacN

r' , (A); Product (A) is :
2 LL\IH4
UJ
I
Br

(a)
%" eHr-NH, cH2NH2

-,.GH2-NH2
(c) q^cH2NH2 (d)

Br
2. In the reactions given below,
(i) KCN' (ii) LiAiH4
R - ct ) ProductA
(i) AgCN, (iil LiAIH+
R_ Cl , product B
the compounds A and B are :

(a) chain isomers (b) position isomers

(c) functional isomers (d) metamers
3. Which is the major product expected from the following S*z reaction ?

crn NaoH ,Product

(a)
,
?"f
v .
(b)
,
oHn
?I
' .

CI OH OH OH
(c)
,
T= .
(d) E?
'
4. Consider the foliowing E1/S*, reaction :

.,^ptn,
,,# -=ffi'" Hgc
+
",.pcHr
The missing product(s) is(are) :

(1) (2)
nag*'
CHs
"r.p,*cH3
t"rrafl (4)

^rr#'^'
(a) Land3 (b) 3 and 4 (c) 2 and 3 (d) 1, 2,3 and 4
 reaction ?

OTs o

,r{AoM"-+hProduct

(u) HgCtH G)
H3C
sr
-'l-H
Ph
H

Me

(c) H-fcH3 (d) H cHg

srtH H Br
Ph
6. Select the reagent that will yield the greater amount of substitution on reaction with
CH3 -CH 2 -Br :
(a) CH,CH2OK in dimethyl sulfoxide (DMSO)
(b) (CH 3 ) 3 COK in dimethyl sulfoxide (DMSO)
(c) Both (a) and (b) will give comparable amounts of substitution
(d) Neither (a) nor (b) will give any amount of substitution
7. Under the specified conditions, substrate X undergoes substitution and elimination reactions
to give products A-D. A and B are stereoisomers, but not enantiomers. C and D are
enantiomers. A is not an isomer of C. Which of the following could be the starting material X ?
x H'o
A
rA+B+c+D

s'd CH"

(r) (m) ( ) (rv)

Hsc ".H
5neH,
(a) (D (b) (II) (c) (III) (d) 0v)
cHs
I

8. CH3 CHs, CHs CH3

-C-I -CH-CH3,
I -CH-Br
(c)
Br Br
(a) (b)

Compare rate of E2 reaction :

(a)c>b>a (b)c>b>c (c) b>a>c (d)c>a>b

9. Which reaction results in the formation of a pair of enantiomers ?

-_----)
CN-
.,, n"
(a)
DMSO
A\: '
n"taj,,,,, oH- , cH3oH
(c)
\L' __D*F-, @6 >

(,

L0. Rate limiting S

*r follows the sequence
6@ 60
n-ni =-[F sr6l-= F6lBr6l ==-lE6l--m
(o) (b) (c)

True statement about sequence on the basis of assumption that R contains 3 different groups
is:
(a) more stable carbocation, greater is in the proportion of racemization
(b) the more nucleophilic the solvent greater in the proportion of inversion
(c) In above sequence (b) represent separately solvated, pair of ions
(d) All of these
1L. Compare the rwo methods shown for the preparation of carboxylic acids :
1' co2
Mettrod 1 : RBr- ;J=--RMgBr
euler
otetn!'l - >RCO2H
2. H3O-

Method 2 : RBr N'N >RCN

H2o' HCI
>RCo2H
heat

Which one of the following statements correctly describes this conversion ?

-+
co2H

(a) Both method 1 and method 2 are appropriate for carrying out this conversion
(b) Neither method 1 nor method 2 is appropriate for carrying out this conversion
(c) Method 1 will work well, but method 2 is not appropriate
(d) Method 2 will work well, but method 1 is not appropriate
12. Which of the following statements is true ?
(a) CH3CHzS- is both a stronger base and more nucleophilic than CH3CH2O-
(b) CH3CHzS - is a stronger base but is less nucleophilic than CH3CH2O-
(c). CHTCHzS- is a weaker base but is more nucleophilic than CH3CH2O-
(d.) CH3CHzS- is both a weaker base and less nucleophilic than CH3CH2O-
13. In the given pair of alcohols, in which pair second alcohol is more reactive than first towards
hydrogen bromide ?

o,*Xn and
u'
,or-d' "ro >cH-cH3
OH
(c) CH, -CH-CH2 -CH3 and CH: -CHz - CH -CH2 -OH
OH CH:
(d) CH3 -CH-CH2 -CH3 and (CHslzCl-CH2 -CH3
OH OH
14. V/hich product would be expected to predominate in the given reaction ?

9SO2CF3

CH,OH
A(30'C)

g- soz - cHs
(c) (d) None of these

L5. Which is the major product of the following reaction ?

.N
(
NaoH(excess)
, Product
Hzo
CH2- Br heat

o -N
II (
orfi'-oH
\'A'cH2- cH2- oH
Br
 o
il

(c)e(::, (d)

t'#lH
16. Arc. KoH r,o, product orthis reaction is :

#or
,u#
V o)

17. Rate of S
*z r€dction is :
Br Br

k Br

d o
I

(a) (B) > (A)

j?, (B)
(b) (c) > (A) > (B)
(c)

(c) (A) > (B) > (C) (d) (A) > (c) > (B)
18. l-2-dichloro ethane + NaSCH2CHTSNa-+ C+H6S z + @)
Unknown product (P) of the above reaction is :

,",(t)
\s, ",()
(c) H-S-C =C-CH=CH-S-H (d) H-! =f-.r=cH-s-H
il'i HH
.rBr

MoistAszo,
19. A (A) Product
Major product (A) is :

(a)A
lo'
o)A
),oH
,rd
KCN
20.. , MeO.- -Cl > Product of reaction is :

\-/
(MOM chloride)
.. (Methoxy methyl chloride)
 cl\,/t* (b)MeO- ,CN
tul \,/
-CN
(c) Me-O*CH2 -CHz -CN (d) o<cN
21. In the given pair of compound, in which pair the second compound is more reactive than first
toward S*z t€sction ?

(a),AAclor o) (n--cHz-ctorO-.,
@.4../"o. X../" (d)

22. which compound might be synthesized by the t-j1}.#.fi;[l" alkyl-halide ?

o)L_,
,",
O-cHz-oH T

(c) Me3C -OCH3 (d) All of these

29. IdentifyC in the following series CaHzI-PO -YLr#--C.
(a) (CHs )rCH -CN (b) CH2 = CH -CH2CN
(c) Br -CH = CH -CN (d) CH2 = CH -CHCN
I

Br
What sequence of reagents is required to accomplish the following transformation ?

# -,,
*
(a) (1) NBS, ROOR (2) CH3CHzO- (3) 2HBr (4) NH, (5) disiamyl borane (6) H2O2,OH-
(b) (1) C12 hv (2) OH-, heat; (3) 2HCl (4)
^,-.
OH-, heat (5) HgSOa, H2SO4
ot'*
(c) (1) NBS, ROOR; OH-, DMSO
(d) (1) Br2, hv (2) r-butoxide (3) BH3, THF (4) H2O2, OH-
25. Which of the reagents shown below would accomplish the following transformations?
Br OH

A
A L.A
--s 2.8 ' A B
(a) H3O+ BHe -THF; H2O2INaOH
(b) NaoH BHs -THF; H2O2,/NaOH
(c) HBr in ether Hg(OAc)z /H2O; NaBH4
(d)NaNHz Hg(OAc)z /H2O; NaBHa
26. What are the products obtained from the following reaction ?

"fr-:*'
@B' 'Product
 H##ffiffi# ##

2Oo/o 800/o 2Oo/a

m 800/o

(d)
.c2' TOAo/o
IOOo/o H'
27. The back-side attack on 2-bromobutane by methoxide (CH3O*) gives the product showrr
below. Which Fischer projection represents 2-bromobutane used as the reactant in this
reaction ?

ocH3
I
product : Et"hMe
H

Et Et Me Br
(a) Me+H I

I
rul H*sr (c) nrfn cal u"*H
Br Me Et Et
28. Consider the following statements :

(1) BridgeheadhalidesareinerttowardsbothS*r andS*z r€&Ctions (tilloneof theringsize

is eight member ring)
(2) The first step in both S
*r and E1 reactions is the same
(3) S rezlCtions proceed with total retention of configuration
*z
(4) Ez eliminations are by the use of a solvent of low polariry and high concentration of a
strong base
Which of the above statements are correct?
(a) I,2 and 4 (b) 1 and 3
(c) 2,3 and 4 (d) 1, 2,3 and 4
29. Consider the following alcohols :

cH2oH
g'H2oH gcH2oH
Br'
".g.n'o'.,' (rrr)

The order of decreasing reactivities of these alcohols towards substitution with HBr is
GV)

(a) III>I>IV>II (b)III>I>II>IV

(c) I>III>IV>II (d)t>III>II>rV
 t,,,;.!.,.,.
,.,:.. ;f'lf;.,,,.' i,i F'?':i

30. In solvolysis of l,2-dimethyl propyl p-toluene sulfonate in acetic acid at 75"C, how many
(alkene + substitution) products will be formed ?
(a) 2 (b) 3 (c) 4 (d) 5l
31.. Benzotrichloride reacts with milk of lime to form :
(a) Benzal (b) Benzoic acid (c) Benzyl alcohol (d) Phenol

32. Br -CH2 - (CHz)z -CHz - Br + CH3NH2 ----+ Product of the reaction is :

r"'q7 o)Q q7. (d)q]

I I
'o I
H H
33. The configurations of the reactant and the product in the following reaction, respectively,
are:

CO.CH"J
KCN l'
CHCN
-+ EtOH
I

D
H
(a) R, R (b) R, S (c) S. R (d) s, s
34. 1-4-dichlorohexane (1 mole) -+ Nal (1 mole) '\cetone , Product of the reaction is :

(a) Cl - CHz - CHz - CH- CH2 - CH3

I
(b) I-cHz - CHz - CH-CHz -CrI3 -l
I C1

(c) H2c : cH -::-.r, - cHs (d) I - CHz- CHz - CHz - CH- CH2 - CH3
I

C1

35. AIM halides can be obtained by all methods except :

(a) CHgCH2OH + HCllZnCl2-+ (b) cHs - cHz - cHs - cHz - wlight ,
(c) C2H5OH + NaCl -----+ (d) CH3COOAg + Br 2lCCla ----+
36. In order to prepare 1-chloropropane, which of the following reactants can be employed ?

(a) Propene and HCI in the presence of peroxide

(b) Propene and Cl2 foiiorved by treatment with aq. KOH
(c) Propanol-1 and SOCl2/pyridine
(d) Any of the above can be used
37. Which alkyl halide has maximum density ?
(a) CsHzI (b) c2Hsr (c) CHrI (d) CHs Br
38. Which of the following molecules would have a carbon-halogen bond most susceptible to
nucleophilic substitution ?
(a) 2-fluorobutane (b) 2-chlorobutane
(c) 2-bromobutane (d) 2-iodobutane
39. When benzyl chloride is treated with ethanolic KCN, the major product formed is :
(a) benzyl ethyl ether (b) benzyl alcohol (c) benzyl cyanide (d) benzyl isocyanide
40. Which of the following is most reactive towards nucleophilic substitution reaction ?
(a) CHz : CH - Cl (b) c6Hscl
(c) CHgCH = CHCI (d) CICH2 - CH = CHz
4L. Which of the following reaction will not give ether as a major product ?
(a) CH3CH2C1 + AgzO(dry) -----) (b) (CH3 )a CCI + CHTCH2O-Na*
CH: -->
(d) cH3cl+Na+o- - I- an,-----+
I

CHs
o
42. e-[-e PP{tt
{8<
tu,
Product (A) and (B) in above reaction is
o o
:
oo
(a)
il
O-- S-O-H,O--
il ilil
s-o-cHe G)o-- s-o-H,o-- *f
-l -cHs
o-
o o o o
II
ll
(c) O-
-
S
-O -CH3, d-*U
-H (d)o--=s-o,
^il
o-- s -o-
lr

cHs
I I
H CH:

i
(d) I
 IfifiIffi
rreffi

1. The following organic halide derivatives (A to J) are reacted in ethanol solution with each of
the nucleophiles : acetate, methylthiolate, cyanide and hydroxide anions. Six possible results
from these combinations of reactants are designated (1) through (6) below :
Write the number corresponding to your best estimate of the outcome of each reaction in the
appropriate answer box below.

Possible Outcome :
(1) No reaction (2) Substitution
(3) Elimination (4) Substitution and elimination
(5) No reaction or slow substitution (6) No reaction or slow elimination
siaiq{!ifif,i
:r: iili liii;iriiiliii

i'ii;r*l:i;r,:'l
;,iii.ffil riiiiiiffiir iiffil$fil
ililli;xliill,iiiixi
:lirrilffiit jililtiil

:]:,it r:r,i,.:,r'ij:;:ltiitir:l,ii',,:;lirrtj:
(iI ur*#*u,ifinu

i(ii) eH6$il$ft

tiffi fi{'fiGNl

t*$. $I $,H
itffi$'ilnill

2. In each of the following sections three organic halogen compounds are listed. In the box
given enter a number (1 to 3) indicating the order of reactiviry of the designated (1 is most
reactive and 3 is least).
(a) S*z substitution byarlaOCOCH3 in methanol:
1: CH3CHTCH,BT I 2. (CHs)rCHBr tl 3. CH2 : CHCHzBT I
(b) S*z substitution by NaI in acetone:
1. C6HsCl [ 2. C6H5CH2CI tr 3. C6H5CHCICH3 tr
(c) S*. substitution by NaCN in methanol:
1. CH3CH2CI f 2. CH3CH2F I 3. CH3CH2I r
(d) S*, substitution by NaSCH, in methanol:
1. (CH3 )2CHCH2CHzBr [ 2. CH3CHTCHBTCH2CH3E 3. (CH3 )3CCH2Br I
3. Isoburyl alcohol (2-methyl-1-propanol), (CHs)TCHCUTOFI, can be rransformed to each of
the compounds (a through 1) listed in the left-hand column. In each case the number of steps
needed to accomplish the change is noted, and an answer box is provided for your reagent
selections. Fourteen reagents (designated A through N) are listed in the right-hand column.
Write letters designating the reagent or reagents you believe will achieve the desired
transformation in the box to the right of the product formula. In the case of a multi-step
sequence write the reagents in the order they are to be used. In some cases you may wish to
use a previously prepared compound as a reactant. If so, write the number (a to l)
corresponding to the desired compound.

8. (cHa )2cHCHrBr oae A, Hg(OAc), in H20

b. (CHs)2C : CH2 oae B. PBr, & heat
G; (CHs )2CHCH : O one c. NaBH4 in alcohol
d. (cHs )2CHCO2H one D. LiAlH4 in THF (aqueous workup)
€i (CHs )3CBr tvtrO Ei NaCN in alcohol
f. (CHs )2CHCH2C
=N fuiCI fi+ PCC in CH2CI,
g'iili (cHs )2CHCH2OCOCH3 one fifi! Jones'reagent (CrO, in HrO*)
h. (cHs )2CHCO2C rH, two ,*Ii HBr in CH2Clz
1. (cHs )2CHCH2OCH2 (CH: )z tl^ICI 'Ii H3PO4 and heat
j, (cH: )2coH three J. (CH3CO) zA * pyridine
k. (cH: )2CHCH2NH2 three IL NaN, in aqueous alcohol
tr, (FH3 )zCHCH2CHzNH2 | rwo L C6H'CO3H in CH2CI2 (peracid)
M. NaH in ether and heat
N.
9rlgollj'gqT!rly't_&*heo
 s,4:

SUBJECTTVE PHOBLETIS

H3
CH.OH
1.
+?
Br
X =Total number of substitution and elimination product(s). Find the value of X.

1.. ABCD EFGH I J

(i)2221 1162 2 6
(ii)2221 1562 2 6
(iii)2221 1133 2 3
(iv)4221 1533 4 3

2. a-3>L>2; b-2>3>1; c-3 >I>2; d-1>2>3

3. a- B; b -I; c-F; d- G; € - I, H or 2 H; f - B, E or I, E; g - J; h - G, Nor4N
i - N,I; j - I, A, C or 2AC or ILD or 2LD; k-B,K,Dor1KD;1-B,E, D or 1ED or 6D

Subjective Problems
1.4
 .,!i11*ij:-!itr "%
tffi',+-..*i+,1

i{
i#$*#rEffiSH;r:+,*,,.
H#,#,*
'+ma:i$t-ffiil:s'11'

ffilHTffiHi EP0.NilUE

1. The following transformation involves a carbocation rearrangement. The carbocation is

generated by protonation of the hydroxyl group, followed by the loss of water. Which bond
has to migrate in the carbocation to yield the product indicated (after the deprotonation) ?

-----=-+
H2S04

(a) a (b) b (c) c (d) d

2. Identify the major product.

H"SO.
a , >
 Iii:.,r riii;:,i,i.i li

ffiEOI*ab IrffiE4S 1*&Iq Effis,,i,S$',' i,--fiffi

d:;z-oH.n,_!_.,
3. (*/
.\
(A) (major)

i
H

an::,z-o-c-cH3
rul (*,J .,,CYH'-OH
I
I

H I

f-tn,
o
o

ft;,
il
._CHs

,.,(I"' I
cal \*./
I

HH
4. Predict the product when given compound reacts with LiAlHo :

o o
t-ocr,
it tl

,,,
(A)

o o
ll lt
c-o-cHg c-o-cHs

o
il

/,C
H
(d)
${# ,i

5. Predict the product when given compoun d (A, in the above question 4) reacts with NaBHo.
o o
il
c-o-cHs il
c-o-cHs

,"fo,
(d)
o
v OH
o
il il
C_O_H
HCI -^--.C-o-CH3
6. + cH3-o1B-H Catalyst |1}| +H2o

The labelled -O18 will be in

- Methyl benzoate
:

(a) Hro (b) Methyl benzoate

(c) Both (a) and (b) (d) Benzoic acid
co2H cH' - 3H H-
7'
l-.
lrl I
1g > (A); Product (A) is :

co2H cH2 - oH
o o
ll
C-O_CH,
ll
C_O_CH,
's
(a)l I
(b)l I

C_O-CH, C_O_CH"
il ll " '
o o
,80
il
c-o-cHz
oo
(c)l (d) H- O- C- C-
il lt
O - CH2 - CHz - OH
c-o-cHz
I

il
,80

8. Which is oxidized most easily ?

(a) CH. - CHOH - CH, rurftou

(c) CI{, -CH, -O-CH2 -CH3 car3c[i
 OH

s. -&*9.-- (p); product (p) is :

#to'" oo
,"rn (b) (c)
d]-'o" ,orfrco2H
10. Which of the following react with HBr at faster rate ?
OH
(ar Az- OH
curHA.r,
OH
(c).nrffon (d).rr-ft/
OH
11' cHg-8+l-on ---+
cHs-Jr+cH2-oH
Above conversion can be done by :

(a) NaBHo (b) LiAIH q (c) PCC (d) KMnOo

12.
-4891-+
H2SO4, A
al ; product (A) is :

co2H
CO"CH"J
CO"C FIs
l' l'
(.)[A
r&
d
(a) (b) (d)

Y co2H co2cH
\/-\o2cH3
OH
OH Ph
H2so4
L3. Ph > (P) ; unknown (P) of the reaction is :
99o/oYteld

(a)'Ar:l
a\/z
3
o
soH
(c);5;l
3
"'-#*<l
 $fi iu ryfairi, Jrrr
14. Predict the major product of the given reaction.

"* , (A); Product (A) is :

(a)

(c) (d) o xo) Me

15. Identify the major product

ai-O '*'Product

oHO
,^rh -IJ (.,o# ",JN
A
(b)

16.

,rr& ",g]&",.,M,.,"&
o$r /ocH3
17. LiAlH4 (A) Major; product (A) is
> :

co2cH3

,,,
b]]'
cH2oH
,0,
+ oH
(c,+ (d,H"'(ou cH2oH
 .
rglr-rfins AIID EffiEDGf,,.
OH

18. + (A); Compound (A) is

dorr**,u:Ilj*,, :

(Resorcinol)
o
o o
,,,fJ::,.., (b)
il
H-o-c-(cH2)r-c-oH
il

o o
il il
(c) CH, -CHr-CHz-CHz -C-OH (d) cH3 - (cHz), - c- oNa
OH
x.- H'Croa
19. , (A). Product (A) is :
u

,,,d" ,,{
(3o alcohol)

(a) No reaction
co2H

(1)cH'-Li(excess)
,(A) .]?(B) + cHIrJ; compound (B) is :
(z) ut NaoH

Major product obtained in the reaction is

21..
-tr- :
s'il rliiiriiii t'.,,,,...i.,:.:,ii.,, .
',,,.tli,,ir:i,,..11i.i1,..,1..1i1i111i.
I ,'
# ffi #;# i

22. Consider the following alcohols,

(r) (rr)
OrcH2oH orN-.@acH2oH

(rrr)
curo .gcH2oH (ru)
r,gcH2oH
The order of decreasing reactivities of these alcohols towards nucleophilic substitution with
HBr is:
(a) III > I > IV > II (b) ilI > I > II > IV (c) I > III > tV >II (d) I>III>II>IV

^-'
U -
23.
_+(P)
NaBH,

')To 'HHo,(e)

Sum of number of 1'alcoholic groups in product (P) and (Q) is:

(a) 1 (b) 2 (c) 3 (d) s
24. In presence of dil. HCl, compound A is converted to a constitutional isomer (B), compound B
is:

(a) NHz
A O -8-1eD>-*o, o) NH2
AoH
d-4@-*o,
H

(c) NHz
A O
OH

(d)
oo

NHz
).4 Ar
 i : $49
"

zs..nr-pon
CH" Q H
CrOrClo

carbon atom)
dichloro methane
cHg

,rr*O rul-fQ-o
(o)-l-c)
otl
I o
corEt ,cH2oH
26. LiAIH, ; Product of the reaction is:
O
(a) Racemic -+ (b) Diastereomer
(c) Meso (d) Optically pure
OH
I
(t) (3's eq)
27. Co,H EtJ-i
H2o
r (A) ; Chemist added extra 0.5 mole of Et-Li
' (z) H*. 65oo1ield
(,
in above reaction to obtain product (A), rvhich is?
OO ?no
tlaA-c - Et
(a) G)l

#,,
\,

(d)
a*r\r/ I

28 rj"':T, Io-H HCI

Major product of above esterification reaction is:

Hory O
il
- cHz-o-c*Ph
(b)

,,, ,0,
,orycHz-o-Ph *fro-c-Ph
 Ei*tifilffi"$#

(a) S (b) SN, (c) slt (d) sw

*, NGP Ar
- -
AC,O
30. (A); Product (A) of reaction is
--r*il :

o o o
o,,\
"A
6*,Y
OH
"A
(a)

o*,Y (b)
r5 (c) (d)
d*,Y
NHz
o
o o

p..rrct', qncc). cH2cr2

#'
H
31. Product of the reaction is :

cHg -f - o,
cHs

CHO QozH

(c)
O
,koH
i32. Which is the best reagent to co_nvert isopropyl alcohol to isopropyl bromide
?

f" 9H'
cHs-Jr-ou 4 cHs-Jr-r,
(a) HBr (b) SOBr, (c) Br, (d) CHsMgBr
 Ph OH

33.
_>A
HNO2

H cHs

Major product obtained in the above reaction is :

o
rl ,,cHs
ll
o
cr{s
(a) c-Y ll
(b) Ph-c-YF
Ph
- Ph
Ph
(c) Racemic (d) Diastereomers

8il -I%rar {ff!==$ qr;

Total number of stereoisomers of product (B) will be:

(a) 2 (b) 3 (c) 4 (d) s
o
il
s-c-cHs
Bs. {A 1.HO-
,.rl Major product of the reaction is :
\ O_C_CH"
o
ll"

,",(fj: o,<H,,c, ralfTro

\1,.
o
il
s*c-cHs
36. ,o' ,
,ttllO
_C_CH"
ll"
o

ratfTro
LI,
 o
37.
o-+
CHrMgBr lH*
(1)
KMnOo (cold dil. ) CrO, u" lt
(2) (3) (4)
For the above conversion the correct order of reagents used is :
(a) L-+2-+3-+4 (b) 1-+4-->3->2
(c) 7-+4-+2+3 (d) 2 -+ 3 + 4 -+ 7

CH",\
6H:
tn'-.
,q - cH2 - cH3 :.
38. CHrt I +g)
s_ r- C H - cHs 0) , ,n{" iX -
cHg
OH .rrl\,/ -
(3o alcohol) (2" alcohol)

Find missing reagents.

(a) x: LiAIH+,y = NaBHa (b) x: LiAIH+/AlC13 ,! : LiAlH4
(c) x = LiAIH 4, ! =LiAlH4 /AtCl3 (d) x=Hz/Ni, l=HzlPt
39. In,solvolysis of 1, 2-dimethyl propyl p-toluene sulfonate in acetic acid at 75"C, (alkene +
substitution products) will be formed by mechanism ?
(a) SNr, E2 (b) SNr, E1 (c) SN,, E2 (d) SN,, E1
o

LiA]H"
40. (A)

l,e.,o
J
(B)

x : moles of anhydride consumed

(a) 1 (b) z (c) 3 (d) 4
41. Identify product when (R)-and(S)-2- butanol reacts with (R,R) tarraric acid in acidic
medium.
(a) Racemic (b) Diastereomer
(c) Meso (d) Pure enantiomer
42. An alcohol of formula CeH12O reacts with NarCrrO, to form a compound having formula
CeH10O. The original alcohol might be :
OH

,u o) '
@cHz-cHz-cH2-oH @ln-cH2-cH3
CH" CH"
,.,@l-'o, (d)
@ln-cH2oH
cHg
43. An optically active alcohol of formula CrHrrO, produced the following compound when
refluxed with KMnOo.

The original compound showed these properties also :

csHtzgz *' , H2 liberated

(A). \ .. --'
Br^
\ ) no rapid reaction
\ croy'H*
CeHBO3
#
What is structure of (A)?
OH
cH3 oH
Y
(a)
q, o) (c)

6CH:
(d) both (a) and (b)

44. Which are not cleaved by HIO*?

I : glycerol II : glycol
III : 1, 3-propenediol IV : methoxy-2-propanol
(a) I, II, III, IV (b) I, II
(c) II, III (d) IrI, IV
45. Which of the following reactions require an oxidising agent ?
(a) CH, CHz------) CHs
(b) CH3
-CH:
CH2OH------) CH3CHO
-CH2 -CH3
(c) CH,
- CH2CI---+
(d) CH3
- CH2OH-+CH3 CHs
CH3
- CH2CI
- -
What is the major product of the following reaoion ?

NaBH+,
product
A
\AcorH
 OH
:
(a)
q",, (b)

co2H cH2oH
(d)
co2cH3
47 ' Which of the esters shown, after recluction with LiAlH4 and aqueous workup,
will yield nvo
molecules of only a single alcohol ?
(a) CHTCH2CO2CHTCH, (b) C6HsCO2CH2C6Hs
(c) C6H'CO2C6Hs (d) None of these
48. For the following reaction, select the statement that best describes the change.
RCH2OH + pcc [csHsNH*ClCrO;] ________)
(a) The alcohol is oxidized to an acid, and the cr(vl) is reduced
(b) The alcohol is oxidized to an aldehyde, and the cr(vl) is reduced
(c) The alcohol is reduced to an aldehyde, and rhe cr(III) is oxidized
(d) The alcohol is oxidized to a kerone, and the crCvl) is reduced
49. What is the product of the following reaction ?
9Hg pHs cHs
H*C-
"\./ CHg OsOo(cat ), (CH3)3CCOOH H
-1.- oH n -l-- oH Ho -f.-n
H,c:
t-, (cH3)3coH,Ho- H-J-oH HofH '-|_o,
cHs cHs cHs
r23
(a) Only 1 1b) t : 1 mixture of 2 and 3
(c)only2 (d)t:1:lmixtureofl,2,and3
50' An organic compound B is formed by the reaction_of ethylmagnesium iodide (CHrcHrMgI)
with a substance A, followed by trealment with dilute acid. Compound B does not
react with PCC in dichloromethane. IdentifyA ? "qr"or-,
o o
(a) CHs
il il zo\
-C-H
(b) CH3CH2 CCH3 (c) H2C : O (d) H2C- CHz
51'
j'G[:,,
Which of the following reagents would carry out the following transformation
? (D - 2H)

G8.r, D
(a) NaBDo in CH3OH (b) LiAlHo, then DrO
(c) NaBDo in CH,OD (d) LiAIDo, then DrO
52. Which sequence of steps describes the best synthesis of 2-methyl-3-pentanone ?
o
 (a) (1) 1-Propanol + (CH3)2CHMgBr, diethyl ether
(2) H3O*
(3) PCC, CH2C12 ,

(b) (1) 1-Propanol + NarCr2Or, H2SOa, HrO, heat

(2) SOCI2
(3) (CH3)2CHCI, AlCl3
(c) (1) 1-Propanol + PCC, CHzCl2
(2) (CHs)2CHLi, diethyl ether
(3) HrO*
(4) NarCrrOT, H2SO4, HrO, heat
(d) (1) 2-Propanol + NarCrrOr, H2SO4, HrO, heat
(2) CH3CH2CH2Li, diethyl ether
(3) H3O*
(4) PCC, CH2C12
53. Diols (I-M which react with CrO, in aqueous HrSO, and yield products that readily under
go dercarboxylation on heating, are :

(II)Ho^ oH
oHl
(III)HOT (rD,\,z,\OH
OH
(a) I and II (b) II and III (c) II and IV (d) I and IV
5,4. Which of following compounds are not oxidized by HIO*?
cHs cH: :o
(1) -cH-oH
I
(2) -c I

H-C:O
cH2
- oH
cH, :o
(3) -c:o
cHs
I
(4) -c I

cHs cH,
-c -o -cH-NH2
o
(s)Go (6)
cHz
I - ocH3 il
rzl C-OH
cH2
- oH I

cH2 oH
(a) 5,6,7 (b) +, 5,6,7
- (d) 3, 4,5, 6,7
(c) 6,7

ss'%' .z\.,zCH2oH
tlll , (A) --------.
-Pyridine
goc
80'C-+
(HMPI Solvent)
(B) 84o/o;Final product (B) will be :
56. Unknown (A) in the reaction (given in e. 55) is
%,.,%,.,%" :
CH2 - OTs
.^=rcH2oH
(a) ,OH o)L&ors
t_l
(c)

57- In the given table, identify the incorrect option. The digit in box indicate the moles of that
substance.

Reactant HIO4 HCOzH HCHO

consumed formed formed
OH

(a)
I

Ho - CHz - CH- CH2 - OH

OH OH
(b)
ltr
R-CH-CH-CH-CH2-OH
OH

ocH3
(c)
I

HO - CHz - CH- CH2OH

(d) Ho-cH,-H i:,'

58. Succinic acid ^ >(A) *H. >(B) B'b
>(C); product (C) will be :
cH, - co2H cHz - co2H cH, - corK* cH, - co2H
(a) I
(b) I
(c) I
(d)
cH, - cH2 - NH2
I

CH2 - NH2 cH2 - NH2 cHr-cHr-Br

59A. Given are the structures of cyclic D-glucoside. Moles of HIO* consumed with X tnd
respectively:
r-cHoR
I !",
Ro
-cH Io
o-{ l-on
OH
OH L-o,
I
cH2 - oH cH2 - oH
(a (v)
(a) 2,2 (b) 3, 3
(c) 2,3 (d) 3, 2
B. Moles of formic acid formed in X and Y respectively are:
(a) 1,2 (b) 2, L
(c) 2,3 (d) 3, 2
C. Moles of HCHO formed are:
(a) 1, 1 (b) 2,2
(c) 7,2 (d) 2, 1
60. In which of the following group, each member gives positive iodoform test ?

(a) methanol, ethanol, propanone (b) ethanol, isopropanal, methanai

(c) ethanol, ethanal, isopropyl alcohol (d) propanal, propanol-2, propanone
61. Hro" + Na ----) . (B)
[*]
o
il
CH, - C- O - CHz - CH, + (A) --> (C) + (D) alcohol

Product (C) of the reactions is:

o o18
il lt
(a) CHs - C- O- H (b) cH3-c-o-H
o o
ll 18 il
(c) CH, _- C- O- (d) cH3 - c- ooru8

62A..o"d" ______+
H2

(Ph3P)3 RhCl
(A)
0.1 M NaOH
------)
Hzo
(B) + (C)
(Contains no nitrogen)
(Methanol)

Product (B) of the reaction is :

 OH

,"rO
Noz
o
lt
c-o-cHs il

(c)

Noz
",gc-ou
B. Product (C) of above reaction is :

HO OH

Bromine Lucas reaqent

Orange to Green

No reaction No reaction

Compound X and I respectively are :

lt
(a) cH. - cH, - c- cH, ; A.,,\ b) ./\.,^oH ;f"f
il
(d) cH3 - cH' - cHz - c- H;
o
t'"'
64. .. .tt' . ,r
dimethoxv ethane
,M ''9* ,N +cH3oH
\--l
--lo"
Product (M is :

r,tlcH, (b) I -.n,

'o
nlG8-o-H (d) L -.",
65. Assign the structure of major product (X) of the reaction given below.
o
]l^__ cH3cH2oH
CH - ioH i:.'' a > socl.
HCI(e), A
1Y1
I A
OH -\
o o
O-cH-J-o,
r"l \-/
I
o) GcH-J-or,
\--l I
OEt C1
o
(d)
@>cH: cH-[-o-.,
OEt
cl
rll 0 o
lt
66. (}cH-c-ocHz-cHg + CHg-COH-+ (A) + (B)
HCI
acetic acid A, 1.5 h (contains chlorine)
ethyl-2-chloro (7 mole)
2-phenyl acetate
(1 mole)
Product (A) and (B) respectively in the above reaction are :

c'l @cH
\-----../ - J - or, cHs - I - o.rr.r,
cloo I

o) (@)-gH
\--l
- J - or,, cHg - [ - o.n,
cl oo
I

c.l @-cH
\-J
- J - o.,, cHg - I - o,
clo
I

(d) cHz-cl, cH3-8-on

O
o
lt
67. H2C = CH - C- OCH3 + CHTCH2CH2OH -------) (A)
+ CHrOH
methylacrylate n]butyl-atcoh-o1 TsoH, A bpt,145'C bpt 65.C
bpt 81'C bpt 117"C

Product (A) of above reaction is :

o o
ll il
(a) HrC : CH - C- OCH2CHzCHT (b) H2C:CH-C-O-CH(Me),
o
ll il
(c) H2C -CH2 C- OCH3
-l (d) H:C - (CHz)+ - C- O - CH3
ocH3
 i-- OH
68. t OH 3AcrO --)
L gg (acetic anhydride)

In above reaction molecular formula of glycerol increases by :

(a ) C4H4O z (b) C6H6O. (c) CuHuO, (d) c oHoos

69. cive the best conditions for this transformation:

?",
H3CXO HrC*ocH,
(a) CHTOH, H* (cat. ), heat --) (b) H20, H* (cat. ), heat
(c) Mg, ether, CH 3OH (d) socl2, cH3oH
70. Give the major organic product of the following reaction.
o

0 (1) sodium acetylide

(2) H2O,H*,o r"u,rrtr"

On
Product

.,,0
\0
,.,4
l-l
OH OH
(B)
(1) MeMgBr
(z) H'oe q6y *uBno'Eton > qpl
H+
,

Froduct (D) in above reaction is :

QH oH

,rr#
,.r:&
 :m' rc*nfp''Ure@f ,, .:, .','.. t' , ; ' ',','-, i'' : ' ',-.i, ,.,,',,.r'
;:;,. i"i.., ,he best method for the preparation of the following compounds :

and ft'"*on
$.n,
(MCPBA : Metachloro per benzoic acid )
(a) reaction of cyclohexanone with CH3Li
(b) reaction of 1-methylcyclohexene with Hg(OAc), followed by NaBHo
(c) reaction of cyclohexene with BHr; NaOH/HrO2, following by CHrBr
(d) reaction of cyclohexene with MCPBA, followed by CHrMgBr
73. Identify the reagents (1-4), required for the transformations shown and arrange them in
correct order.

(1) I"{H (LiAlH4) (2) OsOo

(3) NaIOo (4) NaBHo
(a) 1+3-+4-+2 (b) 2+3-+1,-+4
(c) 2-+I->3-+4 (d) 1-+2-+3-+4
74. Which describes the best stereochemical aspects of the following reaction ?
GHr
l' n-Dl ) IProduct
H-Br
ph^cD3
OH
(a) Inversion of configuration occurs at the carbon undergoing substitution.
(b) Retention of configuration occurs at the carbon undergoing substitution.
(c) Racemization (loss of configuration) occurs at the carbon undergoing subsritution.
(d) The carbon undergoing substitution is not stereogenic
7s. Which of following is an example of Pinacol-Diazotization ?
o
fl
(a) MerC - CMe, A8- ) Me - C- Cue,
-lt (b) Mezc
-l - cMe, -l:Yr-, Me - [- a*",
I HCI

OH Br oH NH2
 fr H*
(c) MezC
-tt- CMe, '* , Me - b- cu", (d)

OH OH

76. (A) H'o' ) B + C ; (B) and (C) both give *ve iodoform test. Compound (A) is :
cqHloo
H

(b)cHr-c-o-cH2-cHs
I

(a) CH, - CH =CH- O - CH2 - CH3

"l
CH,
(c) CH,
"lt
- C- O-CH2 -CHe (d) both (b) and (c)

CH,
77. A solution of PhTCCO2H in conc. H2SO4 gives (D when poured into methanol X is :
o o
il il
(a) PhsC-C-O-CH3 (b) Ph2CH-C-O-CH3
(c) Ph3C - OCH3 (d) Ph3C - CHs
OH

-d*t-(A) 'Hno
'(B)
Product (B) of the above reaction is :

79.
,u@ *,@ (.)[O- (d)

In the given pair of alcohol, in which pair second alcohol is more reactive than first towards
hydrogen bromide?

(,)'hHu,d
(c) CH, andCH3
-!H-CHz -CH, -CHz -CH-CHz -OH
OH CHs
(d) CH3
- CH- CH2 - CH3 and (CH3 )rf - CH2
- CH3

OH
80. Rank the transition states that occur during the following reaction steps in'brder of
increasing stability (least + most stable)
1. Hsc - 6r, ---+ cHj + Hro
2. (CHs)rC -6n, (CHa)rC* + HrO
3. (CHe )rCH - 6r, ---) (CHe )2CH+ + HrO
(a)l<2<3 (b)Z<3<t (c)t<3<2 (d)2<1<3
g1. ,oraJ.aQfl Mnoz
> (A), product (A) is :

(a) o
- c' ''A/oH 61 ,o'A'A'zcHo
HI

f,H'o
(c) H.,A.A.I-, (d) H., ''A'E-o-,
82. In which of the following reactions hydrogen gas will not be evolved ?

(a) CH, OH Na ,
-CH, - cH'MsBr
(d) cH 3 cH oH *
I
- I
-
CH: cHs
PBr" r/-\
reagent 'l
Ms. ether
/^\ Grignard
83. --1-S' ---\
(B) l-fr) "'o* , (3,4-dimethyl
3-hexanol)
H2S04 J
When Grignard reagent reacts with (B) product (D) will obtained.
Reactant (A) of the above reaction is :

t"ta OH
(b)MoH (c)
f OH
(d)
,\,\
OH

84. (A) t^no , 2(B) ; structure of (A) is :

(Chiral alcohol only)
o o
lt il
(a) CH,-CH-C-O-CH-CH3 O) cH
llEt 3
-cH-c-o-cH -cH -cHs 2

o
(.)aA"{ ratT
o OH

+ Noz
+ Noz
#,ffi

Above conversion can be acheived by :

(a) LiAIH + (b) NaBHo (c) H2 / Ni (d) CrO,

?'?
- coH
s6. qcH + EtoH ,.r --, (860/o)

(Mandelic acid)

Identify product of above Fischer esterification reaction :

O -Et
(a)
I
,zo\
Ph -CH -CO2H (b) Ph-CH-C:O
o
lt
(c) Ph -CH -COrEt (d) Ph _CH _C Et
I
-
I

OH OH
o
il
cHsr /cH2cHzcoH
87. X
cH3Li
>(A) t'rtt , (B) nro* , (C)
oo
l_i
Product (C) of the above reaction is :

ooH
ltt {H OH OH
(a) CH, -C-CH2 2 -C -CH,
tt
(b) cH3 -c -cHr-cH2 -c -cH'
I

cHs
tt
cHs cHs

-o o oo
il
(c) CH, - C- CHz - CH, - C-
il
(d) cH3
ilil
CH3 -c-cH' -c-cH3
88. What is the major product of the following reaction ?
OH
i

CHs -CH -CH2 -CH, -OH--#r.--product

oHO
til oo
ilil
(a) CH, - CH -CH, - C- H (b) cH3 - c- cHz - c- H

'oo oHO
(c) CH, -C-CH, -C-OH
il lt tlt
(d) cH3 -cH -cH, -C-OH
 *;;tffiffi. ', *;tf11ffi : ,.;;1;,;1..iri: ffi:riili.ff#
89. The major reason that phenol is a better Bronsted acid than cyclohexanol is that :"
(a) it is a better proton donor.
(b) the cyclohexyl group is an electron donating group by induction, which destabilizes the
anion formed in the reaction by resonance. t

(c) phenol is able to stabilize the anion formed in the reaction.

(d) the phenyl group is an electron withdrawing group by induction, which stabilizes the
anion formed in the reaction.
90. Which of these reagents would accomplish the following reduction ?
o OH
il I

N =C -CH, -C-CH, -CH =CHr---+ N =C -CH, -3-CHr-CH:CHz

(a) NaBH+ (b) LiAlH4

(c) 1 mole H2, poisoned catalyst, low pressure (d) HrO*

9L.
IdentifyA and B :
cH - co2H CH _ CHO

(a) A= NaBH+ , B :O o)a=NaBH+,8:O

CH _ CHO

-.\
(c) A =LiAlH+,B: (d)A=LiArH+,r=5co2H
O
92. Ph-CH2{H-CH' $ --!&\1a;
OH
Product (A) in above reaction is:
(a) Ph -CH, {H -CHs , (inversion) (b) Ph -CHz {H -CH3, (retention)
OEt OEt
(c) Ph -CH2 {H -CH3, (racemic) (d) Ph -CH : CH -CH,
OEt
o
ll ".H*-
93. Ph-C-O-H+CH, -O18 -H<- (x) + HrO ; IdentifyX:

?
(a) X : Ph - C-OrB -CH3 (Trans esterification )
 o
il
(b) X - Ph -C-O18 -CHr(Esterification reaction)
o
(c) x : il
ph -C-O18
-cH. (Saponification)
o
lt
(d) X: Ph -C-O -CH3 (Hydrolysis)
o
s4. R -oH +H -" -E-<}No2 -g R -o -x-g-*o,
Fastest rate of reaction will be when R is :
cHe
(a) CH,
I

- (b) CH3 -CHz (c) CH, -CH - (d) cH3 -: -

I

cHs cHs
95. Select the correct statement.
(a) Solvolysisof (CHs )2C : CH -CHz -Cl in ethanol is over 6000 times greater than alkyl
chloride (25oC)
(b) CH3 -CH = CH -CH, -OH when reacts with HBr give a mixture of 1-bromo-2-butene
and 3-bromo 1-butene
(c) When solution of 3-buten-2-ol in aqueous sulphuric acid is allowed to stand for one
week, it was found to contain both 3-buten-2-ol and 2-buten-l-ol
(d) Atl of these
OH

96.

(a) H*/1, Zn(Hg), HCI (b) HIo4, LiAlH4

(c) HIoo ,H* lt (d) H./a, HIo4
s7. H2c = cH -cH2 -cHz -tT -.r, +*-ral -ffi-.,[t;%,r,
OH
Compound (C) is :

?,
(a) CH, {H -CHr -CHe
1,
CI
(b)

,t'
HOCH z -CHz -CH, -CHz -CH, -CH2 -Cl

(c) HO -CHz -CH, -CHz {H -CH3

(d) Ho -cHz -cH, -CHz -CHe
fH
CI
 98. Iodoform can be obtained on warming NaOH and iodine with :
o
il
(a) CHTCH2CH(OH)CH, (b) (CH3)'CHCC2H5
(c) cH, (d) (cH3 )2CHCH2OH
-fr-ocH3
o
99. Which of these is a reducing agent ?
(a) CrO rl[* (b) KMnOo
(c) LiAIH + (d) O s

too. #(p);
product (p) in the reaction is:
Gat,
(a)
GcH2oHo)Czt[i, ,o,o{,
cHe

101. CH3
I
*"1!l?q , (P); Product (P) in the reaction is:
-C -CH'I
cool

OH
cHg CH"
(a) CH,
I

(b) cH3 {H
t'
=CHz
-C -CH:

(c) cH,
!" !',
-i -o1-cHs (d) No reaction
cHg cHs
1O2. l, 2, 3 - butanetriol undergoes oxidative cleavage of HIO* . During this process
(a) 1 equivalent of HIO4 consumed & HCO2H & H3C -f
-CO2H are formed
o
(b) 2 equivalents of HIO4 consumed & HCO2FI, HCH : O &CH: -CH: O are formed
(c) 3 equivalents of HIO4 consumed & HCO2H (2 eq.) & 1 eq. of CH3COTH are formed
(d) 2 equivalents of HIO4 consumed & 2 eq. of HCOrH& 1eq. of CHrCH - O is formed
oo
ilil
.rr-:>{-ocH3
103. I I --IlEsE*--+ (A); Product (A) of the reaction is :
(ii) H2o (e6o/o)
\r/
o(roH oH o{ -curou
-
o
&.H2
,",$ o) d^12-\-'1 ,.,t-LLZvL (d)$
 oo
ll so ll

Above reaction is/an example of :

(a) esterification (b) saponification

(c) rrans-esterification (d) hydrolysis
1O5. What is the major organic product of the following sequence of reactions ?
o

(cHs)2cHCH2g11---EEh---v Mg , , s'o* >?

OH
"At'
I

(a) (CH, )2 CHCHCH2CH3 (b) (cH3)2GHCHrCH2OH

(c) (CH:)2
?'
CHCH2CHCH3 (d) (cH3 )TGHCHTCH2CH2OH

106. The structure of the product formed in the reaction given below is :

W-T-
,uN,r,M(.)q? w
OH OH

(d)

CHO
I
2HIo4
lo7. CH -oH > Products obtained in the above reaction are :

CH z -oH
(a) HCHO, HCO2H (b) HCHO, 2HCO2H
(c) COT,2HCO2H (d) co2, HCHo, HCO2H
CHO
I

1O8. (QH -OH)s + 4HIO4 ---) Products obtained are :

cH2 -oH
Aldo pentose

(A) 4HCO2H, HCHO (b) 4cH20, HCO2H

(c) COr, 4HCHO (d) co2,3HCo2H, HCHO
CHO cH2oH
,l t''o'
LO9. (i) (9H 9Product '--l
(ii) rcH
I

-OHl, -oH), , Product

..
I

cHz -oH cH2 -oH

 Ratio of moles of formic acid obtained in reaction (i) and reaction (ii) is :

(a) 3/4 (b) +ts (c) 1 (d) s/4

11O. Which of the following compound gives 2HCHO, CO 2, H@ rH when oxidised by periodic acid?
cH2 -oH cHo
cH2 - oH CHO tl
C:O C:O
r"t tfu -oH)z (b)
I

(cH -oH)z (c) I

(d) I

I (cH -oH)z CH _OH

cH2 -oH cH2 -oH I I

cH2 -oH cH2 -oH

111. Hydration of 3-phenylbut-1-ene in dil. H2SOo will give mainly :

(a) 3-Phenylbutan-1-ol G) 3-Phenylbutan-2-ol
(c) 2-Phenylbutan-2-ol (d) 2-Phenylbutan-1-ol
1.L2. Decarboxylation of sodium salicylate with soda lime forms :
(a) Salicylic acid (b) Pheno1 (c) Benzene (d) None of these
Meo-crH
CH _OH
I xHIo+
, What is the maximum value of (x)

"l
I

113. CH -OH O ?

J"I

HC-
I

cH2 - oH
(a) 1 (b) 2 (c) 3 (d) 4
CH" - OH
t"
cH2-oH LiAIH" HoOe
t14. (A)+(B) (C). Product C is ;
H+

ft"
cHg

,rer: H2-cH-oH
*)
\. cH-cH2-oH
I
cHg cHs

(')e(o.Z.X, G)ff
\.:cHz-cH2-oH
I
cHs
 O\,^
115. rz-u'nHtrr_
(A) + CH2 -OH PYridine , !" - -
=Oi
, O)C
cH2-oH
Reactant A of the above reaction is :
o o o
il il
(a) cH, -[-.r, (b) cocl2 (c) CHs -C-cl (d) CH3 -C-oEt

o f,-] [l [l o

--ai a1 _..,
116.
+ co2cH3
(B)'

Identify correct combination

V co2cH3
:
+ cHz
--)
-oH
(c)

+ CHO
(D)
----) + CHO

cH2 -oH
(a) (A) =| O) (B)= NaBH+ (c) (c) = KMno+ (d) (D) = Hsoo
cH2 - sH
It7. In the Libermann's nitroso reaction, sequential changes in the colour of phenol occurs as :
(a) Brown or red ----+ Sreen deep blue (b) Red + deep blue -+ green
(c) Red green -+
white (d) White red --+ green
118. -+
Ethanol when reacts-+ with PClr gives A, POCI3 and HCl. -+A reacts with dry AgrO to form
B(major product) and AgCl. A and B respectively are :
(a) C2HrCl and C2H'OC2H' O) CrHo and CrHrOC2Hs
(c) CrHu andC2H'OC2H' (d) C2H6 and CrHrNO,
il
cH3 _s_cl
(A) & , 1g1 ',o*
I
119. CHs -(CHz), -ou > 15:1
",fi-->
Product (C) is :

(a) CHg -(CHr)3 -CO2H (b) cH3 - (cH2)3 -'4 corH

o
il
(c) CHs -CO2H (d) cH3 -c-o-
t4
H

t,z0. Choose the best synthesis of phenyl n-propyl ether.

OH

or,o 1. Nametal
(u) L. Na metal
2. CH3CH2CHTBT/
polar,aprotic solvent
"r.&o' 2. Ph-Br
 ,cHs
o

,ro -+*Hh OH
to'rr.S'-#
.-..P
l.t2.-.
-
I

Nazcr'9/Hzsor
, The product obtained is :

HO
oo o

(a)"'1),',"$ / (c)

.0 (d) None of these

HO H co2H
l,22. What is true for the equilibrium reaction ?
oo
ll.,rll
cHe -c-oH + cH, -oH Eg'= cHs -c-o -cHs + Hro
(a) The use of equimolar quantities of CH3OH and CHTCOOH will give the greatest yield of
the ester at equilibrium
(b) Removal of water will increase the amount of ester at equilibrium
(c) Addition of CH3COOCH. will cause the formation of equal an equal number of moles of
water
(d) Application of pressure increases the amount of ester at equilibrium
123. PCC (Pyndinium dtloro dromate) is a good reagent for whidr of the following transformations ?
ooH OH o

,,0-.+ a +
",0 o
OH CI o
FozH

124.
(c)o---+
o ",0.* uo,"
How many primary alcohols (including stereoisomers) are possible with formula CsH12O ?
(a) Two (b) Three
(c) Four (d) Five
t,2S. L-Phenylethanol can be prepared bythe reaction of benzaldehyde with the product obtained
in the reaction benseen:
(a) CH,I and Mg (b) CrHsI and Mg
(c) CHrBr and AlCl3 (d) CH3OH and ZnCl,
 126' 0'092I of compound with the molecular formula crHroron
cHrMglgives' 67'00 mL of methane at srP. The numbei of"active reaction with an excess of
hydrogen atoms present in
a molecule of the compound is :
(a) one (b) rwo
(c) three (d) four
127. Migratory apti tude of the following in decreasing order is :

+6 OMe
6O
Y cl Me
(a) (b) (c) (d)
(a) a>c>b>d (b) a>d>b>c
(c) a>d>c>b (d)b>c>a>b
128. The major product formed in the reaction is :

(^A^ ',o* ,
^ 'o- 'o-/cH2R
?

(a) I^ X+ RCH2oH
\o/ z--- G)
'"' f-
i]oA ofrr*
(c) + RCH2oH t' rn" .r''n
-
nb CHo
129' Reaction of R-2-butanol withp-toluenesulphonyl chloride pyridine
in then LiBr gives :
(a) n-z-butyl bromide
G) s-z-uutyl tosylate
(c) R-2-buryl tosylate (d) S_2_butyl bromide
13o' optically active 2-octanol rapidly loses its optical activiry when exposed
to :
(a) dilute acid (b) dilute base (c) light (d) humidiry
13L' If (+; 2-methyl butanoic acid were esterified by- reaction with
1-r) 2-butanol, how many
optically active compounds would be present in ihe final equilibriurn
,uu.iion mixture ?
(a)2 O)s (c) 4 (d)6
o
il
cH3-c-cl

-_Z
Prdduct Z of above reaction is :
 o
o-8-cH,J
"-n-cHg
,",M o
il
",ffi. o
ll

t.rffio-c-cHa
HOH
,o,Mo-c-cHg
\,/

t"ffi
L33.
-ffi(A) ; Identify the product :

(a) No reaction
HH
\,/
o
,.rq' (d) Ph
il

- c- Ph

L34. lntO)2CHCHO + CH3MgI ''o* , (A)

Product obtained in the above reaction is :

oo OH
(a) CH,
lt il
H (b) cH3 -{H
I

-C-C- -CHO
o
il
(c) CH, (d) CIr, {H -CHz -OH
-C-CH2 -OH I

OH

: *'oo
135. Reaction - (1): CHe
- CH -ffi,-- (A)
CH
- > (B) 2 mole
CH,

Reaction - (2): CHs CH : CH CU, --S9lI{9u* (C) 2 mole

- -
Product (B) and (C) respectively are :

(a) CHTCHO, CH3CO,H (b) cH3cozH, cH3cHo

(c) CHTCHO in both reaction (d) CH3COzH in both reaction
 TsCl LiAlH,
136. Pyridine,25'C Pyridine, 25"C

CI

(d)
oo
tg7. HO - (CHz)u - OH, this conversion can be achieved by
-+ then LiAlHo
(a) Or,Zn, (b) O3/H2O2, then LiAlH4
(c) cold dil. KMnOa, HIO4, then LiAIH4 (d) All of these
13t. Which of the following alcohol on treatment with HCI give 3-chloro-3-methyl cyclohexene
as a product ?
CH"
l"
,"r# to'0* ,.r5 (d) All of these

OH

139. # (A); Product of the reaction is :

O 9Hs

(a)e(; o)G::, .nt\OH

'?toH
,.rd
14O. Esterification (shown below) is a reaction converting a carboxylic acid to its ester. It involves
only the carbonyl carbon. Esterification of (-) -lactic acid with methanol yields (+)-methyl
lactate. Assuming that there are no side reactions, what is true about this reaction ?
OH OH
,1.., o" HCI>
cH3oH )+.ocHs
I
(-) (+)
I
(a) An S*z process has occurred, inverting the absolute configuration of the chiral center
(b) An S*r r€?ction at the chiral center has inverted the optical rotation
(c),A diastereomer has been produced; diastereomers have different physical properties
including optical rotation
(d) Optical rotation is not directly related to absolute configuration, so the change in sign of
. rotation is merely a coincidence
141. Which of the following sets of reagents, used in the order shown, would successfully
accomplish the conversion shown ?
oQHs.
GI*,-Glr.r,.H2cH3
(a) CH3CH2CH2MgBT; H3O*; PCC, CH2CI2
(b) CH3CH2CH2MgBT; H3O*; H2SOa, heat PCC, CH2CI2
(c) (c6H5l,i-E HcH2cH s,B2H6i cH3co2H
(d) (c6Hr), i-E HcHrcH3; H2O
o
-L=-ro2Et (l) H1o* ) Product
142. l- T (2)^
; Product of the reaction is :

\-/
o o o o

(a)
ScHo o)
O ,.rf" (d)u
143. Which of the following compound on hydrolysis followed by heating gives a product, which
gives positive iodoform test?
CO"Et
o l'
il
(a) CHr-qH -C -CHz -CHs
corEt
I
",--[*"
9?
(c) CH3-TH -CorEt ,o,ay'-o-Et
corEt
144. Treatment of a 2" OH with Ctfo-slH2SOo yields ar/a:
(a) aldehyde (b) carbo:rylic acid (c) ester (d) ketone

d'.
145. Esterification of the acid P with the alcohols Q will give :

OH
"st"

(S)-P (*)-Q
(a) only one enantiomer (b) a mixture of diastereomers
(c) a mixture of enantiomers (d) only one diastereomer
 OrEt
- H"O/L

Identify major product of the reaction, when the given compound is hydrolysed and heated
strongly:
OH OH
o'",rrfio
(a)

HO2C
(c)

+OH
(d)
#
co2H

9o
*o-8a--Jlq
147. " I I O find out the reactivity order with LiAlHo:

rcHo
cocl
ei

(a) A >B>C >D (b)B>C>D>A

(c) D>C>B>A (d)r>D>c>A
L48. Find out the reaction in which obtained product give positive isocyanide test:
oo
il il
,,,Q)ANu,3\, ol
Q[*H, NuBHo>

149.

In the above given compound how many functional group reduced by LAH (Lithium
alurninium hydride ) and SBH (sodium borohydride) respectively ?
(a) 4,4 (b) 4, g (c) 3,4 (d) 4, z
15O. An unknown compound (A) (molarmass :180) on acylation gives a product
= 390) than find the number of hydroxyl group present in compound (A).
(a) s (b) 6 (c)
(d) 110
151. Which of the following compound is differentiated by NaHCO, as well as by NaOH ?

CO"H OH OH cH2-oH

,rrd O
CO,H CH"-OH
,rr6
OH
o
l' l'
,.,o o (d)

152. Arrange the following compounds in order of their reactiviry toward LiAlH4.
ooo
A*"n'
*
i
\-Jii 111

(a) i<ii<iii (b) i <iii< l1

(c) ii<i<iii (d) ii <iii< i
1.53. Choose the staternent that is true about A,B and C in the foilowing separation scheme.

Ether - =- -)A
Evanorare
Naphthalene flaYer
// Ether Evaporare.
+Hh -n,
llul

\ layer -'*r"^--- > B

\ \dr Aqueous Make basic wi th
-.1 -
layer 10%o NaOH

tetrahydro-
isoquinoline ACUeOUS7v Evaporate - ,.-

layer
(a) A =tetrahydroisoquinoline, B =naphthalene and C = inorganic ions such as Na- and
cl-
(b) A =naphthalene, B =tetrahydroisoquinoline and C =inorganic ions such as Na- and CI-
(c) A =inorganic ions such as Nan andCl-,8 =nzphthalene andC =tetrahydroisoquinoline
(d) A =inorganicionssuchasNa* andCl-,8 =flaphthaleneandC =tetrahydroisoquinoline
 OH

o
1s4 CH2-OH xHI , value
of x is :

\.r,
o-cH3
(a) z (b) s (c) 4 (d) s

rss. qco2H NaBH+

, tal-S--rrl
.o*rorr,]h*tI
o

(a)
@0
o

(c)
o0" (d) (a) and (c) both
I 1. (c) *, (a) 8. (b) '*; (c) D. (b) 6. (b) 7, o) 8i (a)
9. (b) to. (b) I1.. (b) trt; (b) tg; (a) t& (a) 15. (a) I.6. (a)
17. (d) tr8. (a) l9r (b) 2;fi'* (a) 2t.t: (a) *D" (a) 23. (d) t4. (a)
25.. (b) 26. (b) 27, (b) e8l (b) 29,, (c) 80,. (c) 3tr. (b) 32. (b)
33. (a) ?4. (b) s5. (b) $s* (c) 87,i (c) 88; (c) 99. (d) 40. (c)
41. (b) 42. (b) 43. (d) &i (d) *$; (b) 46. (a) 4'7. (b) 4.8. (b)
49, (a) 50. (b) S,l" (a) s2.; (c) s$ll (c) *r (c) illt. (b) ,s6. (a)
57,, (d) s8, (c) 59. A-d $9i B-b Sgi C-a 60I (c) 6r. (c) ffi,. A-b
62. B-b 63. (b) 64" (c) 65. (b) 66, (a) 67. (a) 68. (d) 69. (a)
y$ (c) 71. o) 72. (d) 7'.. (d) 74. (c) 75.. o) 76. (d) 77.' (c)
7.8. (c) 7,,9. (d) 80, (c) 8r.. (c) 8.2. (d) 83. (a) 84. (b) 85. o)
86. (c) 8,7. (c) 88. (b) 89. (d) 90. (a) 91. (c) 92. o) 93. (b)
94,. (a) 95. (d) 9'6, (b) 97, (c) 98. (a) 99. (c) 1o0. (a) 101; (d)
'IIl2,. (b) 10s, (c) ro4. (c) IOf;i (d) li06. (c) ro7. (b) 1{I8. (a) .1O91 (c)
11o; (d) 111. (c) t:72r (b) 11er (b) t'14; (b) TIE. (b) 1 ,6; (d) tt7. (b)
ilI8. (a) ll.g; (b) r20: (a) t.2I' (a) t22. (b) 1*&. (b) I.2,4. (d) 125. (a)
I26i (c) t27, (b) tZS. (c) 1eg. (d) r30. (a) I$n. (c) rg,Ei (b) LB3. (c)
is4. (b) lSSn (a) !86u (c) rs7. (d) 139. (d) r$9. (b) 14(}. (d) tr4tr. (c)
t$frJ (b) I*gt (b) T44" (d) I4Si (b) tr46. (c) ,47. o) 148. (a) 149. (d)
15(}. (a) trE1; (c) 153: (d) 153.; (b) L54. (b) 155. (a)
1. Consider the pairs of ethers, numbered I through V, shown below. To the right of each pair is
a description of reaction conditions to be applied to each. One compound of the pair will
react more rapidly than the other.
Which ether of the naro will be more rapidly cleaved?
Writ
rt answer ln bo x.

H3

O=CHg
I. Treatedl li4
H3 cH3cN,4o"c ,

Hsc
HH3
Itr H'C Tre# ,r r$O jI
mdgffi,ffi, ;i,

&
:[Hi Treated with,HrS0;
.,.
iu,ffi5ffiii#Ss$l,:,'

cH3o
&
,fv. Treated with SYo aqueous
H2SOa, 2${", ",ui1'

\, OlCH(CHs)z
&r O/CH(Cq)z Treated with aqueous
5olo
v.
H;SO*, 25"C
 #:
ffi
(a) CHs -CHz -CHz -CHz -CHz -OH (b) CH3 -CH, -CHr-fH -CH3
OH

.T,
(c) CH, -CHz -CHz -CHs (d) cH3 -cHz
{H
5" ir:"
cHs cHs
I
(0 cH3 -cH{H
I

(e) CHs -CH -CH z -CHz -OH -CH3

I

OH

cHs cHs
I I

(g) HO -CHz-CH -CHz -CHs (h) cH3 { -cH' -oH

I

cHs
Above compounds (a) to (h) are isomers of C'H12O.

Based on the above isomer answer the following (A to F).

A. Which isomer is most reactive towards dehydration by conc. H2SO4?
B. Which isomer will undergo rearrangement when treated with conc. H2SO4?
C. Which isomers on dehydration with conc. H2SO* give alkene which is capable to show
geometrical isomerism ?

D. Which isomer is least acidic ?

E. Which isomers on dehydration give most stable alkene ?

F. Which isomer on dehydration with conc. H3PO4 undergo maximum rearrangement ?

 ,.
ffi
l',,,
R+,cHi+,W
",i:;:.'
' ri.,,l #l B[.]r:r11;r'"r;:1;.1
#ffi+#m
IOI r, Oxidhtion [,H],,*,,Redueti
Consider the above setuencb,affi.ausW* td,F;

A. Conversion (CH, -CHs-----) CH3 -CHz -OH) alkane--+ alcohol is achieved by:
(a) Brrlhv, alc. KOH (b) Brrlh% aq. KOH
(c) BrrlCClo, LiAIH4 (d) Br2lCCla, NaBHo
B. Conversion R - CHz -OH-+ R -CHO can be done by:
(a) PCC/CH2CI2 G) Cu, 300oC
(c) CrO, (d) Allof these
c. Conversion R -CHO--+ R -CO2H can be done by:
(a) KMnO + (b) HrCrOo
(c) KrCr2O, (d) All of these
D. Conversion R -CO2H---+ R -CHO can be done by:
(a) LiAIH 4 (b) NaBHo
(c) DIBAL - H (d) All of these
E. Conversion R -CHO ----) R -CH2 -OH can be done by:
(a) LiAIH + (b) NaBHo
(c) H 2 /Ni (d) Atl of these
F. Reduction R -CH2 -OH-+ R -CH3 can be done by:
(a) LiAIH+ O) NaBHo -AlCl3
(c) H2 - Ni (d) Red P + HI
4. Which of the followinq is true for a

fi.ffii This,compbund,rnay be c{assified as afi atdehide.

This ComB nd rnay be dassified,as,-a tsae

aldoi rea takes place on mbatment' ffi'Na0H solution.

There is,mb reaction with LiAIH; in e$et solution.

Tffi An excess of CHrMgtsr in ether reacts to give 4-me&yl-2-pentanol.

,#.t i lVolff'I{ishner.,reduction gives butane.

This compound;is an isomer of 3-pentanone.

 5. This problem is an introduction to the planning of multistep syntheses.
For use, you have six reactant compounds (A through F) ; and eight reagents (1 through 8),
shown below. ,

Following these lists, five multistep syntheses are outlined. For each of these, certain
reactants or reagents must be identified by writing an appropriate letter or number in
designated answer boxes. Write a single letter or number, indicating your choice of the best
reactant or reagent, in each answer box.

Reactant Gompounds :

O (A) (B) ,',,.,,:

.

(Cli
. j: :

.,:,rr,
A (D)
_(; "E:lt
(E)
G)

Reagents
(1) Jones' reagent [NarCr2Orin HrO+ ] (2) PCC [CrOs in pyridine + HCI]
(3) Sodium hydride NaH (4) Sodium borohydride NaBHo
(s) Thionyl chloride SOCI2 (6) Phosphorus tribromide PBr,
(7) Aluminium trichloride AlCl, (8) Magnesium turnings in ether

*
1.
ry*2
-
#ffiE- ceHrzo2
Reasentf,,
f "a'
o

z.*ffi'Tt c3H6o,#ffiffiqf
e.
ftoH trffiF c6H1oo2
ffi O<-cH2cHzcHs

(I), NaO.*{:*olfition
Reactaar (Xi xeagqrlt[]
4, 'drH;6
[3] Reactant[

Reactant
(1) Reagentfl
(2) ReaaantlTl 1
!D.
fiHffiE c3H7Br
(3) Hror+r
-1?-o,
 e is true for 3-methvl-2-butanone?
:,., ifl,r ,
It may be prepared by cro, oxidation of 2-methyl-z-butanol.

b. Its reaction with NaBHu gives a secondary alcohol.

G. It may be prepared by acidic Hg2* catalyzed furdration of a.methyl.l-butyn6.

d* It forms a silver mirror on treatment with [Agffi3 )21+

G.r This compound is an isomer of 4-penten-1.-ol.

7. Which of these methods would serve to Drelrare 1 t?

l]'-:* --**.ry
I :, ::, r i;::

Ii' f,.., EVYLHTYV" I

rde (ethanal).

b. Addition of phenyl lithium to propylene oxide (methyloxirane).

C. Addition of phenyl Grignard reagent to acetone (2-propanone).

,4. Acid-catalrzed hydration (addition of water to) of 2-phenyl-1-propene.

G
ll'
,,,1
Addition of methyl Grignard reagent to acetophenone (methyl phenyl ketone).
:,tl

il 191i,,", of methyl Grignard reagenr to phenylacetaldehyde.

8. Match the Column (I) and (II).

9. Match the Column (I) and (II).
 H .' '],' :'r:r '1,:q

rtgr-ffi_rilfi,:l Og, t'.,,.,.,5,.If,.Ir .,;l

Qff,, , ' :i: :ii:i'.'.

cH2oH

oH sHro,
oH
OH
--- : ..
,:,,,,,,

cH2oH

Ratio of moles of fotrnaldehyde obtalned in the reaction (1) and reacdon (2) ?

: of the simptrest,;gly [,,'bf,ffiis,'g5, ei':irBinacol, and this type of reaction therefore is named
, 't pinacol rearrangemeni Gn.,&ic,rpetfrfic,cas3, the reactibn is called a-pinacol-pinacolone
realrangerngn0.. The rearrangement involves 4 gtery. 9ne g,f the hydroryl groups_ is
protonated in the first:,s . A raolc"f l.df Water is relfRinated in rhe second step and a
,, ,terti4ry carbocation is,formed. The Carbocation rearranges in the third step into a more
stable carboxonium ion via a [1, 2] rearrangement. In the last step, the carboxonium ion is
deprotonated and the product ketoue is obiained,
Me Me

oH-.ffiHo
H,SO,

A. 'What is R.D.S. of pinacol-pinacolone rearrangement ?

(a) I step (b) II step
(c) III step (d) IV step
 H"SO,
B. HO OH+ HO oH-+
Et Ph
How many products obtained in above reaction ?

(a) 1 (b) 2 (c) 3 (d) +

OH

c. f^-l-cH2-cl AgNos
>p
Il ^
Product'P' is :
o
o o

(a)
A (b) ,.r0 (d)
A
D. .nr#.r, -YN?':, 1a,

oH NH2

Product fal; '

a",
ill
(a) cH,
- c- f -.t, (b) cHg

CHs OH OH

(c)>< (d) None of these

SUB.E.GIf,I.UE,FHOBLEIIilS

cH:o
1. (A; 4 moles of Pcc ,

cH:o
Maximum number of moles of AcrO consumed by reactant (A) is :
 1. I-B; II-A; III-A; IV-B; V-B
2. A-d; B-a,c,e,f,g,h; C-a,b,c; D-d; E-d,e,f,g,h; F-e
3. A-b; B-d, C-d, D-c, E-d; F-d
4. arcrerg

s' u**rtr,
ry*2-"'#ff,E cs'72o2
Oa']fo
o
Reactant
E Reasentlrl,
c3H6o2
#ffit +&
Reagentffi f,*
\V
heat

+"' ffi
---1,
c6H1oo2
ffi O-< - cH2cHzcHe

*"ffit ReasentEr
,c3H6offi -#*o*3
Reactant il) Reagent@ J
:il'- 8#-"*## c3H,Br
ffi |on
f,
6. b,c,e 7. a,b,f
8" ,-p,b-r,c-S,d-q 9. o-s,b-rrc-e,d-p
L0. Ratio of reaction I and Il : 2 L1. A-b; B-b; C-c; D-a

Subjective Problems
1.4
1'v N2H4/KOH/H2O
(Wolff -Kishner reduction)
(A)
major
; Product A is :

Noz

OH C1

Noz Noz
CI OH
 o
lt

2.q'-": cH2
- cH3

o
CHz-CHz-NMe3 CHz-CHz-NMe3
Above conversion can be achieved by :

(a) Wolf-Kishner reduction (b) Clemmensen reduction

(c) LiAIH+ (d) NaBH+
o
il
B. CHe-C-CHz- CHz- CH-CH" -------) CHs- (CHz)s-CH
"
\,/oo \,/-9H,
Above conversion can be achieved by :

(a) Wolff- Kishner reduction

(b) Clemmensen reduction
(c) HS CHz CHz SH, following by Raney Ni
- -
(d) None of these
-
o
I
!
I
-.r,
Zn(Hg)
4. f'A
t-:A. , ; product of the clemmensen reduction is :
HCI
rrloz
OH OH

| "
I I
cH2 cH3 cH
- cHq cH? cH3 cH2 cH3
l' -
- t- -
t")@*o, to'@*o, t"@*, tu'@*o,
OH o OH
I il I

5. CH3 CHz ----) CHg CH- (CHz)s CHs

-CH -CH2 - -C -CH3 - -
Above conversion can be achieved by :

(a) Wolff-Kishner reduction (b) Clemmensen reduction

(c) LiAlHa (d) NaBH+
 o
ll
c-cH3
)ffre> q cHz- cHz- CH2-CH3

**q (B)
Q OH
(P)

Identify product (A) & (B) from the given product P,QR:
Q?C1
(0)
CI
(R)

(a)A=P,B=Q G)a-Q,B=R (c)A=g B=P (d) a =R, B:P

o
il
c-cH3
Zn(Hg) (A); Identify
7. , the A.
HCI
HO

cH2 cH3
-
(a)

(
(c).rA
o
lt
C- cHg

6
Y (
NzH+

HO-,A
Wolff- Kishner reduction)
Product (A) is :

cHz
- CHz- Br
cH2
- cH3

,rrq
cHz-cHz-oH
(b)

6
rffi , : ,'. .,:,,'t-t,-,
tti'

(
(c) ra ,.r6
CHz-CH2-Br cH cH3

r
I
-
r-l
o\,ro
Br

9.

Above conversion can be carried out by'

(a) Clemmensen reduction (b) Wolff-Kishner reduction
(c) LiAjH4 (d) NaBHa
10. Increasing order of equilibrium constants for the formation of a hydrate:

NHz

NHz ozN
(D (III)
(a) IV < III<II<I G)rv<IIt< I<II
(c) I<II <III<IV (d) tr <rrr < r <IV

I 1'
@ c-c -OocH3 #ffi? rrau;o.$ia,.,
Product (A) is:

o
,,,OI-.n,+ocH3 o)@f-.n,-OocH3
OH

,,
G.r,-[6rocH3 (d)
OcH,-cH-@-ocH3
OH
 Me Me
Predict the product of hydrolysis of the above molecule.
o

"li.rx-"-H
(a) (-1..
co2H

cHs

o
o

(c)&!-"-H (d,A
OH OH co2H

13
f"'-+f"'
oHo
(a) tvterco/u* , H3o@, KMnoa luo-
, This conversion can be achieved by

(b) olru*, KMno4, Hao*

Me2C
:

(c) KMnOo/NaOa, lvIerCO/H*, HeO* (d) KMnoa/Naloa, HgO*,MerCO/H*

\:\oX s'oo A + B.compound
14. > (A) & (B) can be differentiated by:
(a) 2-4-DNP (b) Fehling solution
(c) Lucas reagent (d) NaHSOs
OMe
o
L5. ,k:T:
trimethyl
+
Uo
non''.''"t''*' ,(A)+";j;*xe; product (A) is:

orthoformate

(a)e)<:il" G)eJ<:il: (c)eJ<;T'(d)eltil:

 Reagents to carry out above conversiofl, P, Q, R respectively are :

(a) HzC : CH CHz Br, (HOo ),IHO@, A], Wacker-process

--
(b) H2C : CH-CHz Br(HO@), Wacker-process, HO@,A
-
(c) Wacker process, HzC : CH CHz Br(HOo ), HOo (l)
- -
(d) Wacker process, HO@ (a), HzC : CH CHz er(HO@ )
- -
o corP
17.5.. f[-o-o-'-,
Above reaction is a BaeyerVilliger rearrangement of an asymmetric ketone with magnesium
mono peroxo pthalate hexahydrate (in the drawing, Mg*' is omitted for clearity) Identify
major product.
o o o

!o,* (b)/.-'[o
*-Ao OH
,"r(, \ (c)
(,
(d)
\--AR
18. ffot"u,,o er"' ,

Above compounds can be differentiated by following reagent:

(a) 2-4 DNP (Brady reagent) (b) Tollen's reagent
(c) Lucas reagent (d) NaHSOs
OH
f3fi
OH PCC (excesr) 1 equivalent, CHsMggt, *urno>
lg. , (A)
\--l
Hi
(81
H:0-
1C; 1p1

Product (D) will be :

OH OH
-

''51'-"'
,OH
(b)

OH
OH

(c). OH
 BH3'rHF
Hror,6H
> rpl cH2cl2 tql
20. CH3-CH: CH2

ffi() (r)

Relationship benareen products (Q) and (S) is:

isomer
(a) Positional (b) Chain isomer
(c) Stereoisomer (d) Functional isomer

zt. In the reaction, o

ffix, the product (x) is :

G
(a) ,o,w OH

,.rN
22. Rank the following in order of increasing value of the equilibrium constant for hydration,
Kr,ra. (smallest value first).

("
o

D-"
lr
(cH3)3ccc(cH3)3
1

(a) 7<2<3 (b) 3 <\<2 (c) 2<7<3 (d) 2 < 3 < 1

2s.*
t_l
a
L_l
Above conversion can be achieved by:
(a) Zn(Hg), HCI (b) NH2 NH2/KOH/A
-
(c) LiAlH4 (d) H2lNi
24. Which sequence represents the best synthesis of hexanal ?

cH3cH2cH2cH2cH2cH o
Hexanal - o
il
(a) 1. CH3CH zCHz CH2Br + NaC -CH (b) 1.CH3CH2CH2CH :CHz +CHTCOOH
2. H2O, H2SOa, HgSOa 2. CH3MgBr, diethyl ether
3. H3O+
4. PCC, CH2CL2
o
lt
(c) (d) 1. CH3CH2CH2CH2MgBT + HrC
1. CH3CH 1CH2CH2C CH3
"VZ
-
CH,

o
lt
OOg 3. LiAlH4
2. CH3 c 2. H3O+ 3. PCC, CH}C|}
4. HzO 5. PCC, CH2C12
o

HNo3 ca(oH)z
zs. >(A1 ,(B), product (B) in this reaction is :

O o
o o

o'flo
cH2oH
o)
A CH2O1
,rA (d)
0
26.
HO
H
HHO (?)x
]-:>"-Ph
o
H OHH OH

cH2 oH cH2 oH
- -
Compound (x) in the above reaction is :

o o
il ll
(a) Ph-C-CH3 (b) Ph-C-H
o o
ll il
(c) Ph-CHz-C-H (d) Ph
- cHz
- c- cH3
 o
H'o.
-tr --fa)-ffi181
il
27. Ph-c-cH, >1c;

Product (C) of the above reaction is :

o
lt
(a) Ph
-
CO 2H (b) Ph
- oc- co2H
oo
llll ll

- c-
(c) Ph C-C- H (d) Ph cH2oH
-
o
il
H-c-H > (al (B) ; Product (B) of the reaction is
2HCI
-_4sNq-- :

(a) CHz NOz (b) Ph cHz oNo

(c)
Ph
- - - -
(d) Ph-o-N:o
Ph CHO
-

B., , (A) ;
0.75 mole o/o,
nggoTol
AlCl3 Et2O

product (A) of the above reaction is Oromination occur not in the benzene ring) :

OBrO

(a) (b)

o
ll

,r6rof-"'
+i{e r lodoform test

:b Tollens test

-'l:- :: I
. H"O
drop of H2SO4
Positive Js||gn5 test

Compound (A) is :

o o QCH:
il
C-CH- (b) cH3
lll
c-
(a) CH.
- ll'
CH2
- j;,r'
ocH3 ocH3
 o o
il lt
- C- CHz -
(c) CHs CH oCH3 (d) H_C-CH ocH3
I
- z
-cHz -cH I
-
ocH3 ocH3

31. CroHto o. , (B) NH2-NH2 ) ; Reactant (A) in this reacrion is

(A) cBHBo Ho-/a
:

Pht'
(u)'h\c: ,"" to' - , ,"n'
-toh
ph/ a ar, .n/c
Ph.
(c) tc- c/--'
Ph -

(d) both (b) and (c)

cH{ t .n,
c7H:,4o2
Haoo'
s2' (. (-_o-H
1-methyl 1-cyclohexyl +ive +ive *ive test with
hydrogen peroxide
Iodoform 2-4DNP CrO3
test test
Compound (P) is :

o
il
- C-
(a) CHs
- CH- CH3
CHz CHz CHz
- -
OH

ooH
ilt cHz _
- c-
(b) cHs
- CH- CHz - CH2 CH3

o
il
(c) CHs C-CHz
- -CHz -CHz -CHz -CH2 -OH

ooH
ilt
- c- cH
(d) cH3 c
llr - -cH?
cHs cHs
 Griqnard reagent?
r^wards Grignt
compoundsc towards
;;t;;:r;to.t "t reactiviry of following
o o
o
cHs
ll
H-C-H
ll cHr-8o
-c-H
(I)
(D
0u)

(c) II>III>I (d) I>III>II

(a) I>II>III (b) II>I>lII

anr-@
I HcHo > (A) ; product (A) is :
cH.-cH-cH-cH2-oH
"l TsOH,A 93o/o

OH
' cHr-Ph
Ph
cHgv^. I

-l
(a) I *.,t"*
o-"''o
o-.-o

cHr
I
CH-Ph

,ro
I

OI
ss.
il
c'z- cHz
- cH --Q- ocH2cHzcHs ffi-
(cH3)3co
- - c
oH ocH3
in above reaction is :
Total number of products obtained
(b) 3
(a) 2
(d) s
(c) 4
36. What reagent and/or reaction conditions would you choose to bring about the
following conversion?
,-\ o-
(-}lrl ----
GcH: o +HocH2cH2oH

(a) 1. LiAIH4, 2. HzO (b) HzO, H2SOa, heat

(c) HzO, NaOH, heat (d) PCC, CH2CI2
o
,At MeI excess
KH excess
Bz. (, , Bto/oyield ; Product of the reaction is :

v
o

$
o o o

(a)
Iy (b) (c) (} (d)

38. HO
Cts8 ----+ HO

The above reduction can be best carried out by :

(a) Clemmensen reduction (b) Wofff-Kishner reduction

(c) NaBHo (d) None of these
39. CHe
-C - 611---trAe-;1a;
dil. H2so4

CHa : 6H (1)BHg'THF
r1rl
-C (2)H2O2/HO-

Product (A) and (B) is differentiated by:

(a) 2-4-DNP (b) NaOI (c) Na-metal (d) NaHSO3
 .iffi

40. A
HCN
)tat--!4!r-rrl-ff--+rcl
End product (C) in above reaction is :

OH
o o o

41,
.,0 *,dl' (.rft
Compound (X) C4H8O, which reacts with 2, 4-DNP derivative and gives negative haloform
(d)&t,,
test is :
o
lt
(a) CH: (b) cHs cH cHo
-C-CH2-CH3 - -
CH:
oH
(c)
,<o^ (d) cHs
I

L_l -cHz -cH - cHs

42. When a nucleophile encounters a ketone, the site of attack is :
(a) the carbon atom of the carbonyl
(b) the oxygen atom of the carbonyl
(c) both the carbon and oxygen atoms, rvith equal probabiliry
(d) no attack occurs as ketones do not react with nucleophiles
43. The correct order of rate of reaction toward nucleophilic addition reaction:
CHO CHO CHO o
o il
ri
C_Ph
cHs-c-Et
Noz
(a) (b) (a)
(a)a>b>c>d>e (b)a>b>d>c>e
(c) a>d>e>b>c (d)o>b>e>d>c
io
44. The struc,ur. L would be best classified as a(an)
_, t- 6p1
:

H
(a) Acetal (b) Hemiacetal (c) Hydrate (d) Cyanohydrin
45. Which of the following pairs of reactants is most effective in forming an enamine ?

oo
(a) cHsc"r[n + [(cH: )2cHizNH ,r, + cH3
- NH
- cHs
O
 il
(c) (CHs )rCCH + (CH, )2NH (d) None of these form an enamine.
46. The reaction of C6H'CH : CHCHO with LiAlH4 gives :

(a) C6H5CH2CH2CH2OH (b) C6HsCH CHCHzOH

(c) C 6HsCH2CH2CHO
-
(d) c6HscH2cHoHCH3

42. A
---\
NaBH+
,cal-$--+14;; product (B) of the reaction is :

,^,dl tr OH
o) (c) r: ,rd\,
48. Which of following compound is hemiacetal ?

HOH
(a) ,o)ryo' (c)x (d) all of these

49. Ph CHz C : N
cH:I, 7f/o ; End product of the reaction will be
- - -+?#-+
:

(a) Ph-CHz-CHz-NHz (b) Ph CHz NHz

(c) Ph-CH-C - N (d) - -
Ph-CH:(:N-CH3
I

CHs
3lt
50. Ph
-CH:CH-C-CH3-----) Ph-CH: CH-CO2H
Above conversion can be achieved by :

(a) KMnOo, A followed by H* (b) I2/NaOH followed by H*

(c) HzlPt (d) LiAlH4

Hgo@
5L. > Products ; Product of the reaction is/are :

OH

ror;90, (c) HCHO (d) Both (a) and (c)

OH
,oH
s2. /\ seoz , (A); Product (A) of the reaction is :

\-/
o o

.,0 (d)
*"
o

sB. Ad[:H,
\,,/ -----r ^ +:_,.;
-,.,-}..% q) * cHBr3 ; product (c) of the reaction is :

o o o o

(a)
o-n ,rr5 (c,oG, ,0,ff"'
54.
ooo \ Hroo r (A)+2Glycol

Product (A) of the reaction will be :

o o
ll lt
(a) CHa C-CH2
-CHz -C-CHz
o - o -CHs
il ll
(b) cH3
-cHz -c-cHz
o o -c-cH3
-cHz
il il
(c) CHg C-CHz
o -
-CHz o -C -CH3
il lt
(d) cHs
o
-c-cHz-c-cH3
il
55. R-NHz :N
R
- C
- n rR
- cH
-R. This reaction gives best yield at :

(a) pH1-2 (b)pH4-s (c) pH 10 - 11 (d) pH t3 - L4

56. An aromatic compound Aof the molecular formulaCsHloO on reaction with iodine and
dilute NaOH gives a yellow precipitate. The structure of the compound is expected to be:

,u@fi-.,, (b) c6HscHoHCH3

o
(c).rr$cH2oH 101 .n,-(g!o,
K.n,
 is treated with acidified potassium dichromate to
form a product B(molecular formula C3HoO). B forms a shining silver mirror on warming
with ammonical silver nitrate, B when treated with an aqueous solution of NH2NHCONH2
and sodium acetate gives a product C. trdentify the structure of c.
(a) CHgCH2CH : NNHCONH2 (b) cH3c,: NHHCONH2
cHs
(c) .rrf : NCoNHNH2 (d) CH3CH2CH : NCONHNH2
CH:
58. In the reaction, the acid obtained will be :

cH3cHo + HCN ---) CH3CH(OH)CN H-oH > CH3CH(OH)COOH

(a) D-isomer (b) L-isomer
(c) (80%oD + 20o/oL,) mixture (d) (500/oD + 50%L) mixture
59. In the following sequence :

CH3CH2C1 NacN , (i) -- xitrz-- (ii) @ (iii), product (iii) is :

(a) CH3CH2CH2NH2 (b) cH3cH2cH2coNHCH3
(c) CHTCH2CH2NHCOCH3 (d) cH3cH2cH2coNHCOCH3
o
lt
C-H
KMnOa\
--'----a H,Co
-'sJ . fZl\
- HzQa

Product (G) is :

o
il

(b)
Ho_;:@-co2H
o
ll
HO co2H C-H
(c) (d)
HO
61". Carbonyl compounds can generally be converted to hydrocarbons by :
(a) HzlPt (b) LiAlH4 (c) N2H4-KOH/A (d) K2Cr2O7 - H2SO4

L_,/ LL-**=--
Gz. [\u, rot, product (A) is :

[3]ft9afl,
(4) Ho

oo o o

arr&r. ,.,d*
(b) (c)

+Et
 Which statement about the aldol condensation is correct ?
(a) A Lewis acid is commonly used as a catalyst
(b) The initial step is probably the formation of a carbanion '
(c) A Lewis base is employed to induce carbocation formation
(d) The carbon chain is lengthened through the elimination of 1 mole of water
64. A compound gives a positive test with I2/NaOH and is extracted from benzene by saturated
NaHSO3. It may be :
(a) CHs (CHz)4CHO (b) cH3 (cHz)3cocH3
(c) CH3CH2COCHzCH3 (d) cH3 (cH2)4cH2oH
65. Which of the following compounds on reaction with excess CH3MgBr and subsequent
hydrolysis will give a tertiary alcohol?
(a) C 2H 5CHO (b) c2Hsco2cH3 (c) c2HscooH {a) cHs(fHCH3
o
oN-OH

66. A+B-------,d
Reactant (A) and (B) is :

(a) Ph-CH2-CH : O+ NH2-OH (b)Ph-CH:O+NH2-OH

o o
il il
(c) Ph-C-CHs + NH2-NHz (d) Ph-C-CH3 + NHr-OH
o
ll .a(oH),
67. CHs-C-OH-(A)
Product (A) is :

A
o
b)No (b)

OH
(c),A.
I

@), ,/oH
\tVhich of the following does not form a stable hydrate on addition of H2O ?

ooo
lllril
(a) Ph-C-C-C-Ph (b)
69. Consider the following sequence of reactions.

Ketone o j#'lse-, :*j%, ;#;h1- +

A
The ketone (A) is

(.)\af
:

r"tJo (b)
o o
(d))r
o
70. In the reaction,

. cH3cocHs
-Effi x, the product (x) is :

O
,rrffi ,rrffx'
,.,+.<::: (d)
A zcHz

7L.
dr..r,
The conversion of acetophenone into benzoic acid can be achieved by its reaction with :

(a) sodium hydroxide followed by acidification

(b) iodine and sodium hydroxide, followed by acidification
(c) hydroxylamine followed by reaction with H2SO4
(d) m-chloroperoxobenzoic acid
72. In which of the following compounds the methylenic hydrogens are the most acidic ?
(a) CHTCOCH2CH3 (b) cH3cH2cooc2Hs
(c) CH3CH2CH(COOC 2H5 )2 (d) cH3cocH2cN
73. Which is the major product of the following reaction ?

o "H5

,o
74.
- l]
Ph-C-OH-----:,
socrr
(A)-
H.,
+ (B)
--= -
Pd-Basoa

Product (B) is :
 o
il
(a) Ph-C-H (b) pn-cH2
(c) Ph-CH2-Cl -OH
(d) Pn-CH : CHz
.

75. The presence of unsaturation in organic compounds can be tested

with :
(a) Schiffs reagent (b) Tollens'reagent (c) Fehling's reagent (d) Baeyer,s
reagent
76, Which of the following gives iodoform test ?
(a) CHgCH2OH (b) CzHsCHo (c) (CHzoH)z (d) None of these
77 ' Which of the followingpketo carboxytic acid does not undergo decarboxylation

,,A
on heating ?

*,fft:2H
/co2H
cHs
(c) (d) None of these

il
78. HocH2cH 2cH2 - c- ocH2cH, --s9-fol
ffi1ry --IEe!UIzg_-g61
o

-++-, Hsoo , ,.rr-trro ,,r,

Hzo Pyridine
Product (D) is :

o
lt
O-C-CH3 O

(a) HzC :
llt
- C-
CH CH CHz CHz Off
- - -
(b) H2C CH-CHz C _CO2H
- - I

OH
oo
(c) Hzc : cH- g ilil
-cHz -cHz -C-o-d-cH,
I

OH
o
(d) H2C : _ lt
-CHz - CH-CHz - t_O
CH H
I
OH
 Which of the following structures best represents the intermediate responsible for this
process?
OH H. .oH oH H. oH

O OH OH HO -OH

80. The final product of the following sequence of reaction is :

(cH3o)2cHCI{2cH,cH2Br u'c:o>
-'* , T:?.
heat
,
o o
ti il
(a) CH3O C CH2CH2CH2CH2OH (b) cHe c cH2cH2cH2cH2oH
o o o
il lt il
(c) HC CH2CH2CH2CH2OH (d) HCCH2CH2CH2CH
81. The amino ketone shown below undergoes a spontaneous cyclization on standing. What is
the major product of this intramolecular reaction ?
o
II
ccH3

cH2cHNH2
I

cHs
cHs
 o o
il il
(a) CH, CH-CH3 (b) cH3
-C-CHz-- -c-cH-cH3
I

cHs cH2-cH3
o o
il ll
(c) H_-C-CH2-CFI-CHs (d) cH3
I
-c-cHz -cHz -cH2 -cH3
cH2--cH3

83.
Q + (1)Et2o
> @); product (A) of the reaction is :

5 *"f*o' 1z;Hroe 99o/o

,rrffio'
Noz

@- *t",
84. o rrvl
-ffi- ror -isga-1n; --e{efp-xo)
O-
Product (Q) will be :

.,,8 ,.,8 ,.,8*

85. Ph CH, --9roz9!z-r1a1-ulKoE-, Ph __ CH2OH + (B)
-
Product (B) of above the reaction is :
(a) Ph Co2H (b) Ph Co, (c) Ph CHO (d) Ph cHs
- - - -
 CHO
86. rilrcN t Product Product obtained in the reaction is :
H _F_I OH (ii)H*
;
I

cH2 oH
D-(+)-Glyceraldehyde-
(a) Diastereomer (b) Racemic
(c) Meso (d) Optically pure enantiomer

87.Go*,*(A)H*>(r)_g_+(C);Product(C)ofthereactionis:
OH

(a,# ,,G* ,o,G*

I I I

H H H

88. Dg-N + CH3MgBr---=) (A)

H:o*
i395 (B) + (C)

Product (A) and (C) is :

o
(a) |
t-. ll
(b)
t1 ll r+
l-/ tsC-CHe; o
CHI3
[_/-c -
cHa ; cHI3

,o Di-cHg;cHI3 (d) cHr3

DcHz-c4Ho;
OH o
il
NH2-NH-C-NH2
89. Ph-CH-CH3
I

(B)
Product (B) is :

cHs o o
(a) Ph-C
til N-C-NH-NH, (b) Ph-Q
ll
- -N-NH-C-NHz
I

cHs
o o
il il
(d) Ph-CH : N-N- C-NH2 (d) Ph-CH : N-C-NH2
I

cHs
 {F-r'r
Product (P) is :

(a) Hemiacetal (b) Acetal (c) Alcohol (d) Alkane

o
gt. ; Product of rearrangement is :

W
(Oxyallyl cation)

,,oq"' *,o(.

OH
o K.q \ -cN
sz.A+ HCN
=- R-a_^
RR
Reactant K"o.

PhCHO a

o
il c
Ph C- CH3
-
o
ll d
CHs
-C-H
The correct order of decreasing value of K.n. is :

(a)a>b>c>d (b)d>a>b>c
(c)d>b>a>c (d)d>o.>c>d
93. Product (B) of the given reaction is :

o o
Me-o-}ro
+ ,oiion
I -+(a)
H*
\ OMe
(B)
base
OH

fl*"
oo
(a)a
lloMe
-,U
---4.
(c)
fl
oo
SO2OMe
--4.
I I so3Me

94. End product (C) of the reaction is :

a
oo
Mo,, HO
H+
OH
(A) 2Phugnr ,181 H,o* >1c1

,,,4 ooHoHo
o

,,Ail* (c)4:4",,,.,{Ann
OH

.: serr aldoi condensation

es. c{a)o< ::.' :"dergo A8
>f Ph CHo + 2b > oxalic acid
-
Compound (A) will be :

(a) Ph-C:C-C:C-CHO (b) Ph-C:C-CH:CH-CHO

(c) Ph-CH:CH-C-C-CHO (d) Ph-CH:CH-C-CH-CO2H

96. 3 )-o, product; product of the reaction is :

U (629oie\ot
,/\ Catalyst TsOH
0'C, 2h
(molecular sieves)

(a) -. oo.-
V
.r .

(')-x
97. Which pair of reactants compounds may be used to make given acetal ?

o
?
"4"
o
(a)

*
+l
cH2

cH2
-
-
oH

oH
(b)
A +x:x
o o

(c) A +X OH
oH (d)
A
oo
98. [,.no '* ,(B); (A) & (B) are isomers ; Isomer (B) is :

(A)

,rrp OH
o)Y":
(c,# OH
,.,ft"] OH

OH
I
occ
99. .,A-. , (A)

(A) and (B) is differentiated by:

(a) NaH (b) 2-4 DNA (c) Tollen's reagent (d) NaHSO3
.
1OO. Which of the following pairs cannot be differentiated by Tollens' reagent ?

(a) Benzaldehyde and benzyl alcohol (b) Hexanal and 2-hexanone

(c) 2-Hexanol and 2-hexanone (d) Pentanal and diethyl ether
1O1. An optically active compound C6H12O gives positive test with 2, 4-dinitrophenyl hydrazine,
but negative with Tollens' reagent, what is the structure of the compound ?

o o
il II
(a) CH, C- CHz CHz CH2 CH3 (b) H-C-CH-CHz
- - - - I
-CH2 -CH3
cHs

o o
il il
(c) CH3 (d) cH3
-C-CH-CH2
l' -CH3 -cHz-c-cH-cH3 I

CHs CHs

lO2. Compound (A) C6H12O3, when treated with 12 in aqueous sodium hydroxide gives yellow
precipitate. When A is treated with Tollens reagent no reaction occur. When A is hydrolysed
and then treated with Tollens reagent, a silver mirror is formed in test tube. Compound (A)
will be :
o o ocH3

(a) CHs
il lll
(b) CHS-C-C CHS
-C -CHz -CHz -CH -OH I l
-
ocH3 ocH3

o o
il il
(c) CHs (d) H C CHz CH(OCH3 )z
-C-CHz -CH(OCH3)2 - - -CHz -

NH2-NH2
1O3. CHz
- CHz
- CO2H
+-rA >r-#(C), Product (C) obtained is :

cHz- cHz
-co2H
o

(a) CHg
-
CH : CH
-
CHz (b) A N- NHz

(.)n (d) A
lO4. Which of following does not react with NaHSO3 (sodium bisulphite)?
oo
(a) cHs
ltll (b) CH3
-C-H
o
-C-Et
o
il il
(c) Et-C-Et (d) Ph-CHz
-C-CH3
cHz
- cHz
- cH2
- NH2 H
105. -Ranfu (A); Product (A) is :

,rrm (b)
@? I
H

,.rm (d)
@?
I I
H H
oWo
: KoH
106.
U
+CH2 CH
- CHz
- Br >
,*)r;
Product (A) is :

CHz-CH:CHz
o\)/o-cHz-cH:cHz l'
o\Ar'o
,r, (b)
(,

o\](:,_cH:cHz
,., (d)

CHz-CH:CHz

toz. ral -jfo--(B) +cHr3; product (B) in this reaction is :

d"',*
CO2Na
CO2Na

,,,502Na G) (c)a (.)6.'

 Arrange the following reagent in the correct order in rvhich above transformation is carried
out :

(a) KOD/DzO, H* ln,LiAlH4 O) u./a, KoD/D2o, LiAlH4

(c) KOD/D2O, LiAlH4, U* ln (d) LiAIH r,H* IL,KODID2O
O

1O9. CHs
il
t- H HCN
>(A) . ,(r) tN'o+(D) HIo4 > HCHO + (E)
- "o* o-+(C)
Compound (C)can show geometrical isomerism. Product (E) of the reaction will be :

o o
it ti
(a) CHs
-
C- CH3 (b) cH3
-cHz
__ c- Fr

(c) CHs CHO (d) HCHO

-
1L0. Arrange in their increasing order of equilibrium constants for hydration ?

o o oo
il il il ll
cHs
-c-cH3,
(A)
cHs
-c-FI,
(B)
cHg
- c- cH2
(c) - cl, H
-_9--
(D)
H,

o
il
cl-cHz-c-H
(E)

(a)A<B<C<D<E (b)A<c<B<E<D
(c)A<C<E<B<D (d)c<A<B<E<D
1LL. End products of the following sequence of reactions are :

1.Iz+NaOH,A__-
I I
\.,A.c cH,
vrr3 z.H-

il - 3.a

(a) yellow ppt. of CHI3 (b) yellow ppt. of CHI3

\, cooH \,,4-cHo

,(c)
yellowppt.ofCHI3 , frO (d) yellow ppt. of cHI3, , C:ooH
\,, V/cooH
 i!; t:::,.:i::! r:!;i l:i I

rii#*m:I
(')"olu
r1,2.
- cN
ph cHz , (P) ; Product (p) of the reaction will be :
-
,rrarr-'l-a,
lelHroo /a

o o
lt il
(a) Ph-CHz-C-H (b) Ph CHz C- CH3
- -
o o
il il
(c) Ph- CH-C-H (d) Ph CH C-CH3
I
- I
-
cHs cHs
o
L13.
Il _
r-
(i)NacN h -- r,- -. - n-.- r-- --- -t -1- - -.-- --.
Products. Products of the reactlon are
v Tr
rr ----)
(ii)H2so4
:

(a) Racemic mixture

(b) Diastereomers
(c) Meso
(d) Mixture of meso compound and optically active compound

11,4. ral;ffi (B) t*'o ,

r"."J.?,*rrr.
.'. reactant (A) is :

(a) CHs (b) HC :CH

-Q -CH
(c) CHs (d) Ph-CH : CHz
-C -C-CH3
o
LL5. CH3CH2
- [- CH. -ffi--+ ; Major product of this reaction is :

o o
il il
(a) CHs CH- C- CH3 (b) CH3
-CHz-C-CH:N-OH
Noo
I

il
(c) CHg C- CH3 (d) cH3 cHz
-c il - cH3
-Cll - -
N-OH N-_OH
116' + (B)' Product (A) & (B) are
d Tffi(A)
:

H
I

OH

o
il
CH

It7. + CH3NO,
-JuoH--a "l' r (B). Product (B) is :
nitromethan. A 93o/o

3,4-Methylene
dioxybenzaldehyde

CH: CH-NO2
(a) Ho (b)
"gCH:cH_Noz
OH
CH: CH-NO2
I

,.r""4 (d)
"gcH-cH2-No2
OH
o

118.
d ffi#]
Product (A) is :

,rd ",[6T^(o,.,@ ,0,@

 G)>-[a
(d) Ho o,
o OH
il
12(J. R HCN - R-J-^
-c-R Gil |

CN

Which of following can be used as a catalyst in the above reaction?

o
il
(a) Cl- (b) CH3
-C-O-
(c) Et-O- (d) HSO;
I21-. Arrange the following carbonyl compounds in decreasing order of their reactivity in
nucleophilic addition reaciton.

CHO CHO COC H3 CHO

d +d 6
-a
Noz cHs
(i) (ii) (iii) (iv)

(a) ii>iii>i>iv (b) ii>i>iv>iii

(c) iii>ii>i>iv (d) iii>i>iv>ii
122. The following reaction were carried out.
H

"Yo rzlNaHCos
,
OH
The final product formed in the above reaction sequence is :

H
A""t--Oo
(a)l I o*u I (b)

Y''" I
 HI ,
(c) .1+"
\/ oH
(d)a\s.\:5o
o*u
\},

tzs. Me3c-[-cHa
i] Me3c-[-cHz :
(B\s4o/o

OH
,zo\ Aao/^
- iH- dr, # - cH
I
Me3c Me3c cHz Br
-
A. Yield of each step as actually carried out in the laboratory is given above. What is overall
yield of reaction?
(a) 42o/o (b) 310/o
(c) 2lo/o (d) 6o0/o
B. What is the appropriate reagent to carry out above synthesis , i. €. , A, B, C respectively are :

@) Brrf H+, LiAlH4, H@ g) srrf H*, NaBHo, Ho-

(c) NBS, AlCl3,HO- @) Yrrf Ho-, BF3, Ho-
OH

& pressure)

Product (E) is :

(a) Nylon 66 (b) Nylon 6 (c) Styrene (d) Polysryrene

125. Methyl vinyl ketone on reaction with LiCuMe2 gives a major product, whose structure is :

(a)Me-)a*' *)4'(#.
HO

o
(c)*':#"' (d) AA
HO
 H
126. Which of following is in capable to show iodoform test ?

(a) cHg (b) Ph-CH:CH-CH-CH3

H2C : CH
OH
Hfl
(c) (d)
@|cHz-c-c,'
ll
A ' callg{95
CHz-l-cHrJY-)"\ \'! Lr
127. CHg C- CH2 (B)
- - A (major)

Product (B) of above reaction is :

,0,w.,
L28.

(d) None of these

LiAlH4
tzg. (A) > (B) +Diastereomers
Symmetrical
Ketone

Reactent (A) is :

o o
il il
(a) CHs (b) cH3
-C-CH3o -c-cHz-cHs
il
(d) cH3 o
(c) CHs
-CHz-C-CH2-CH3 -cHz-cH2-cH -
130. -fr
Cyclobutenone
+x LiAlH4 ether
, HgOo >

(90olo
Cyclobutanol
yield)
+ Li+ and Al3+ Salt

Value of x in above reaction is :

(a) t (b) 2 (c) 3 (d) 4

131. (A) NHroH

frl*$i|-CHs
^
>(a;-tL9A-r(c)--trc98+(D) +
KoH'^ - N3c ph
Ph

(D) socr, >(F)ffi(G)--E'-+ral-ffi

t/\ X
Molecular weight of compound (A) is :

(a) sB (b) 120

(c) 60 (d) 182
o
aqueousacid
132. Ph2CH-[-H ,1o; f enol+aldehyde
g1o/o 2o/o 77o/o
Product (A) of above reaction will be :

OH
I

(a) Ph-C:CH-O (b) Ph2cH cH2

I
-
Ph
OH o
I ll
(c) PhzCH CH- OH (d) Ph2cH-c-cH3
-
133. Which of the following will form stable hydrate ?

(a) CCIgCHO (Chloral)

", O(::i"(Ninhydrin)
(c) (CFg )zCO (d) All of these
t34. The pH at which maximum hydrate is present in an solution of oxaloacetic acid:
oo
lt o
il il
H-O-C-C-CHz-C-O-H
PKo =2'2 PKo = 3.98
(a), pH - o (b) pH = 12
(c), pH - 4 (d)pH:6
 (a)I>II>III (b)lII>II>I (c)I>III>II (d)rrl>r>II
136. Maximum hydration takes place of :

o o o o
il il il il
(a) CFs C CF3 (b) CH3 CCH3 (c) CH3 CH-CCH3 (d) coHs ccoHs
I

C1

137. The conversion, PhCN + PhCOCH3, can be achieved most conveniently by reaction with:
(a) CHaMgBr followed by hydrolysis
(b) Iz NaOH, CH3I
-
(c) dii. H2SOa followed by reaction with CH2N2
(d) LnH followed by reaction with CH3I

138. Gt3gzl5 rsl

In the above reaction, product (B) is:

r"el- o)r
,orF
139. (A)
LiAlH,
-----r--,
Structure ofA is
(B)
uG
;3
@
d ff
:

o o o o

(a)
o+ *,Cfr (c) (d)
 =<>o ._%+HcHo+a;Lf*rrl
Product (B) is :

o o
il il
(a) C-
- C- CHz -
Ph NH CO2H (b) pn NH CO2H
- - -

Ph

141.
Gtarry out (co2H
To above conversion, arrange the following reagents in correct order.
03lZn EtONa / EIOHIA NaOCI H+
(1) (2) (3) G)
(a) 1+3-+2-+4 (b) f -->2-+4-+3
(c) 1-+3 -+4-+2 (d) 1-+2-+3-+4
HOCH2 o
il
142.
I

H2C = CH -CHz -CHz -C -OH

I
-+HF -(A)-rc#,s+(B) + HCHo

cH2 -cH3
Product (B) is:

O CH2- O\ ,tCHz
ilIc
(a) H-C-cHz-cHz-f - o./ \ar,
Et
o
(b)
ll
H-C-CH,-CH,-C
zo\ //cH3
' 'Et'/\o'/C-tan,

o
(c) H-O-C-CH2-
il f"-ot
6Hr-f -s,z
'zcHs
\ar,
Et
,Q
(d)
ll
H-c-.rroA ,zol .zcHg
o/c \.r,
1.43. --€
a
-#
b

Identify appropriate reagents for the above reaction:

(a) o :Br2fCCIa, b =ae.KOH
(b) o =BrzlT+, b =ae. KOH
(c) a=BrzlH+, b=alc.KOH
(d) o :BrzlHO-, b = ag.KOH
OH
PhcHo
144. >(X); Product (X) of this reaction is :
H* 960/o

Ph
Ph I
.CH

,rrA ,o,Aoo
I

CH

(c)A o
(o)4
145. The K"o. values in HCN addition to following aldehydes are in the order :

ooo
H r-A-,
\?
MeO Me2N
(D (r) (III)
(a) I>II>III (b) rr > III > I (c) III >I>II (d)II>I>III
OH o
I K,
1.46. (1) CH3-C-CN .q_
/. +HCN
I

cHs

OH
I
(2) CH3-C-CN +HCN
I H
H
elation between K1 and K2 is :

(a) Kr -K2 (b) I(r > K2 (c) K2 > Ki (d) f, =K2=l

 (a) a is cyanohydrin
(b) Nucleophilic-addition reaction
(c) The above reaction is not shown by alkenes
(d) Nl of these
L48' which of the following compounds (i through v) should not be classified as
an acetal ?

4 (i)

(a) ii and iii

ry)C)Oel.,",
(ii) (iii) (iv)
cH3o ocH3

(b) iv
(c) i (d) none (they are ali acetals)
 ffiP'
I 1. (a) 2. (b) 3. (d) 4. (c) D. (a) 6. (c) 7. (b) 8. (b)
,
9. (b) 10. (c) 11. (c) 12. (c) 18. (b) 14.. (b) 15. (b) 16. (b)
17. (b) 18. (b) lg. (b) 20. (d) 21. (b) 22, (b) 23. (b) 24. (d)
i 2s. (c) 26. (b) 27. (b) 28. (a) 29. (b) 30. (c) 31. (d) 32. (c)
I ss. (b) 3,4, (b) 35. (a) 36. (b) :i7. (c) 39. (d) 39. (b) 40. (a)
4L, (b) 42. (a) 43. (a) 44. (b) 45. (c) 46. (c) 47, (b) 48. (d)
49, (c) 50. (b) 51. (d) 52. (b) 53. (b) 54. (c) bb. (b) 56. (b)
57. (a) 58. (d) 59. (c) 60. (c) 61. (c) 62. (a) 63, (b) 64. (b)
65. (b) 66. (d) 67. (b) 68. (d) 69. (b) 70. (b) 71. (b) 72. (d)
73. (d) 74. (a) 75. (d) 76. (a) 77. (a) v8,. (c) 79. (c) 80, (c)
81. (d) 82. (b) 83. (b) 84. (b) 85, (b) 86. (a) *7, (b) 88. (c)
89. (b) 90. (b) 9r.. (c) 92. (b) 93. (b) 94. (b) 95,. (c) 96. (c)
97. (d) 98. (b) 99. (c) L00. (c) 101. (c) lo2. (c) 103. (c) 104. (c)
t os. 106. (b) ta7.
(c) (d) L08. (c) log. (c) 110. (b) 111. (c) ttg, (b)
113. (b) t1-4. (c) 115. (c) 116. (a) ll7. (b) I_ 18. (a) I 19. (b) 120. (c)
tzt. (b) 122. (b) 123. A-c 128. B-b 124. (b) 125. (a) 126. (c) ,,27. (a)
128. (b) l2g. (c) 130. (a) 131. (a) 132. (c) 133. (d) 134, (a) 135. (a)
135. (a) 137. (a) 138. (b) L3g. (d) 140. (b) I4I. (d) 142. (a) 143. (c)
144. (b) 145. gI1 I46. (b) 147. (d) 149. (d)
 $fi GAfirI,C, :ffteff ri* ry&fi tI, f

1. Select the best choice for example (A to L) from the examples (a to n) given below. Write
your
ur cnolce in the boxx glven.
choice ln siven.
ili#ii:l; An acetal derivative of a ketone. t---
$,,Ii A chiral ketone.
le*r An aldehvde that qives a aldol condensation with itself
.Ili ,An oxime derivative
H,-1.,
D,T
A reaeent that reduces aldehldes to 1"- alcohols.
f;iiir An cr. B-unsaturated ketone.
i.iei
-$ reaqent that oxidizes aldehvdes to carboxylic acids.
r,fr, A reagent that reduces ketones to alkanes.
I. An enamine derivative of a ketone.
t An intermediate in imine formation.
:IL A cvclic hemiacetal.
L A svsnp.L.ur4pn ds *
tffiEr,]yt Es A.$& KE',roittm$

^tr
cHs-cHe-aa,
^10
J

2.
which compounot ;r; I
-ffi;-;;;;;.f-
The follorving questions refer to the compounds (A to G) shown below :

lVhich compound are

:.
!

j*' reduced by sodium I ii. lhydrolyzed by hot I iii. oxidisized

. t. . I
by
I
!:
i
.b919hyclride
? _t *l "qs-.9u1 qgid J* -- - l- - CrO./pyridine?

+
o
A. B. G; DJ

o
o
E. F. G, (" Ir.
*',

3. Match the column:

o
)-/ -1$i:.*
o
(1)KCN
A (2) H +'
>

KCN
Ph-CH2-CI > Nu-addition reaction

(d) (l)#.Tq:+ {sl reaction

lfi- ) [ lNu-suustitutions
 d$ iaftd
4. Complete the following table.

, Consider the following reacrions and answer A and B.

(cHili:c;6*Cn, c*f;*cHz-Br j_$

{,p (cHg3

OH o
l-
t uv'v ,/\
(CH3)3 C-9-CHz-Br Aa 680/o
> (cH3)3c-c-cH2
I
t{H
I
I

A. Suggest a reagent appropriate step (a) the synthesis.

(a) HO-/Br, (1mole) (b) H"/Br, (1 mole)
(c).both (a) and (b) (d) None of these
 ;

B. yield of each srep as actually carried out in laboratory is given above each arrow.,What is
overall yield of the reaction ?
(a) 6o0/o (b) 27o/o (c) 4Oo/o (d) 68%
6.
i
U
il
c-H
v "
c* on,,I,; (l)Acro,AcoNa,a
,141
(2)H"o@,4

o
lr
lt
:
- 6H*
ph C 4r!*!Hn4tali' i
Rea*io$ 2. -CH
CH
- " cHiqH-oH
1B1
-t
tr,
OH
i [eaction B. I
(t)Naot
i

i : ', : i:r
Ph-CH:CH-CH-CH3 (z)n@
,1a,
i*.-;;*;;;ri;i;;r

Degree of unsaturation present in compound (A+B+C)is?

7, Within each set, which compound should be more reactive toward carbonyl addition
reaction ?

B
'ii: :'! : !i!!ill::!lIlil::r1:
:" ..::1!!!lr::{i::i+iiii:1il'-
'. : r.'::''
..:1:,rl,ri,i l
t! :t !tt::!i it i
ll
.
. ...:.:ltt:':t:til:l ti:t trt:t:uil

ClIs ,.;*,C
- CHz
- GIe : Bf

o
ilfiffi cHg
ll
.',:*c-cH2 "' '

-cH;
iffi$$ oaN CI{. .O

o
CH3 C* 11
-
 Match the Column (I) and Column (II).

il Formation of six member

i,{ }
-r**a.-(A)'H'o >frl-ff'--+tcl r#I ring takes place

i;,i
i',,.i
(il NH29H
>(A) H- )frl-#itCl Final product is Ketone
::ll, :l:.tl::
$$##, $i'AnrDKErONEs 4S3

o
il
Ho-+ (A)
cHs -c -cH2 -cH, -CH, - C- H A

Ph Finai product fbrmed will

Hc' r a' react with 2,4-DNP.
cH3 {s}
---+(A) i 2,,{ -di- nitrr:phenyl
hydlazipel_ _

9. Consider reactions A through F. Those r:arbon atoills riir,,ir:rgr',ing r,:hange, as part of a

functional group, are marked as C", C14 or st;lrred. in thr,: .ar*-n sirilwn, eich carbon atom
has either been reduced or oxidized. Your job is tt: ide:ttil',, rire i:hange in oxidation state that
has occurred for each of the marked carbon.

Reduced
CH"CH:CH,
"tz
CH,CHBTCH,BT
t4

(i)B,H5
CH"CH
-- - ri;'' - i"CHz
! (ii) H
-----=_-)CH3CH"CFI
"or.\aoH
,Of{
xidi
4 Reduced
CH3CH2 CH : g NaBH+
-rCH3cH2cH

Oxidized
i'
Hz Q
'72
: C(OH)CzHs rautomerization
+ I{..CCO(_1,,H. l" --l-S*l:f-c-gd
t4
i I oxidized
I

L0. Consider the possible formation of an aldeh'yde or li.i:1i;::e produr:t nrhcn each of the ten
compounds in the column on the left is treatr:d yrith e;rr:h ,ri ihr: reagents shown in the top
row. Check the designated answer box if you beiieve iin aiii.riri,rle or }<etone will be formed.
Assume that the reagents may be present in excess. For eat-ir checkeC reaction, try to draw
the structure of the major product (s).
 .diii!"Gr::

$,H. ::.' ,.. 1,:

ll'::.,'.:::ro.1 ,,

!1 ,& .fi : :

& r.
.Hr
'r
is ,

Yi:::.:..Ir...
:I:.:
_s.H
ffi:itdiiill
Yj':aH:t,:
nr:,:
$ . :iH!
. ':' '\aif ,.:,
I

cHa
")-C- /cH,
v- C-
v \at,
cH{

ffH2-oH
G lHs
'T-l<",
cHr
CH*
l"
cH3-t-oH
cHe
Hsc
r taar,
,/cH3
)c =
Hsc

o,
Hovv"oH
'.

# i
..1:ili,r.rri,ri,ii,,:, . .: I tr ... :.. :

:!ffis$..Ilffi#

Wittig reaction :
The reaction of aphosphorus ylide ryilh an aldehyde (or) ketnoe introduces a ca(bon-carb.on
double bond is place of the carbonyl bond.
o cHz
lt il
R-C-R + Ph3P:CHz---+ R-C-R + Ph3P-O
Mechanism:
tO F8nn"
Llt rsdHr-Ynrr,
@ ---+ I l:-''
R-l-.',
^-U (Nucleophilicaddition
oehin%r*ermediate)
J

O-PPh3+R-C-R
i"' (- R-QsCHz
?;r 1nn'

R
l'
(oxaphosphetane

Driving force of the reaction is high bond un.rlt)"#?$9 ol (AH * -ve)

o

A. - Ph3P : CH2 ---) (A) (major), Major product (A) is :

O
QHs QHs CH- cHs

(a,d
o
il
(b)
o (c)
O (d)
0
B. CHs , (e). Major product (A) is
-C-CH2-CHz -CHz-CHz-PPh3 --nnot'
:

CH"
l" QHs

(")^
Htt,,-
(c)
A (d)a)
c' cHfficH, .....sH
Ph3P
> (A) , Major product (A) is :

o
(a) ck-2-butene (b) trans-2-butene (c) iso-butene (d) l-butene
436 oft#
o o o
il lt il
D. CHs -C-(CH2)3 - c -cH2 - P (oEt), ___)
ltraH
(A) (cyclic). Product (A) is :

o oo

E.
@()
\-/
It
I
cHs

Identify major product in given intramolecular wittig reaction

O
(c)
#" :
(o)"t
Rxn.-l --)
lt
CH: -_ C_- CH2 CH(CO zEt)z + HrC : CH
oPPh, *ut , (A)
- -

--+ qil " + H2c: cH- @pph,

Rxn.-2
--) (B)

"'.,{!H;Xi &
Product (A) and (B) respectively are

m
:

(b,&xl;xl & q?
(c,1;rXl;Xl & q?
(d,ry;l;il & @
CH2 - Br
(l ) Ph.:P(2 nrole)
-,: irrr,-u -' (A) ; product (A) is :

CH2 - tsr' i:j iiro

I

CI{O
 *c,r
12. Match the column :
 (') *1.'lo
rol dil.,,lf,t?l r trl , cH3-
H2SO4 e)U@t n -c-cH2-cH3
,
il :'
cH_cH3

A. Reactant (A) is :

(a) CH3 :
-C
C_-CH-CH3 (b) HC
- C-C-C-C
I I

cHs C-C
(c) CH3
-CH--C
: CH (d) cHs-c : c-cH2-cH2-CH3
I

cH2
-cH3
B. Product (B) is :

(a)).--'.- \-- (b) A-(

o

o o
@ /\/.. .-./ (d)
r^
.ALDETTW)ES AND ItrT1OITIES

1. A-l; B-g; C-n; D-k; E-h; F-c; G-j; H-f; I-m; J-d; K-e; L-b
2. i-A, B, C, E, F; ii- D, G, H; iii-B, E, F

3. a-p,rib-r;c-s;d-p,.
OH
I

4. A: Ph-CH-CHr; B:Ph-CHz-COOH; C:Ph-CH:C(t'',

'CH,
o
il
cHz-c-cH3

cHz-c-cH3
il
o

5. A-c;B-b
6. A+B+C =77
7. set 1 - A; set 2 - A; set 3 - B; set 4 - B; set 5 - A; set 6 - B; set 7 - B;
setB-B; set9-A; set 10-B
8. A-p, e, si B-p; C-p,9, s; D-p, e, S

g. A:bothareoxidized; B:C12 isreduced,Cla isoxidized; C:reduced; D:oxidized

E : C12 is reduced, C'4 is oxidized; F : C12 is reduced, C1a is oxidized
 4*{} ORGAIUIC:Chsmii *,
1_O.
-"""--i"^" "*:
IX
th
# i o,q;1
r'1 ; d.d
b".lHiu fr H.,
s' i ld
Yod
drt
ia'
e t*H
fi
(JU I
iiEq
6J!
J.
*.:,,' -r.,
Comrpouxld !,.8
hriZ i a(: ;H
,il+ll-a
jRE
yt "Gi.'
fll
*a
. .i!6 s{
i-a
E.v. tE
i _ra.E Lr. I t.Fr
ll{.
s a.l>
I
I Ar
E8 .H H ftT. iE[.r$,
;'r+,
# i 'q5
:AY
l-f L-r
!4 +r .l
eil
r:.14
h, irl
,.: t:tiH::t

i
t
i
,/ x x x x
I
t

CH,, .i
'>-C: ,-* :I
ix' x /
CH{ ri
i" x / /
._1 i

-j---. ..,-......
t!
rl I
I
,!

i€'lr/
ir
:I
x / x x
ll

ii x ,/ x x
-r- I---iI
I
I
-'
(/
l

l{
I

I
)( / ,/ /
i
i__-___
!
I
I
I
I

)( x x X x x

fi x x / ,/ ,/

./
i__l X x / /
i
i-----::Z-- **-.-.-

13:nz"'l- --i ""..*4" 1r' I

{ x x x x
!

,/
1

t/
,tt d x x x
i c4g oH
I

I
I
I

11-, A - a; Ii - a, L-- --h: [i h: ti -;i; I] , h

1,2, a -.1; b-- s; c - r; ri * p lB. A. (c) B. (d)
 Compound A and B, both were treated with NaoH, producing a single compound
c'
L.
OO
cHg cHs
Ho- > C. Compound (C) is :

heat

o
ll
o

(a) A o
o

(c)
5 (d) A
 ; This conversion can be achieved by :

(a) Dehydration, Hydrolysis

(b) Retro aldol and funher condensation
(c) Perkin condensation & Clemmensen reduction
(d) Clemmensen and Perkin condensation
3. This is an example of an intramolecular aldol reaction :

H2so4 (A); Product (A) is

> :
Hzo

o o
o o

(a)
bo (b)bO (c)
do Ao (d)

o o
il il Ho- /
4. CHg
-C-CH2-CHz-CHz ^ > (A) ; Product (A) is :
-CHz-C-H (73o/o)

o
o il o
f -.r, il

(a)
O (b)
A flltn'
r.r .T'cHo G)dc-cH3
5. Ph CH : CHCHO + CH3CH CHCHO (A) 87o/o; Product of this reaction is
- - ;ffi;, :

(a)
- Ph
- CH)z
- CHO
(Cu Ph
- CH) 3CHO (b) (CH
Ph-(CH:CH)+CHO
(c) -
(d)Ph-CH:CH-CH:CH-CHa
6. CH3CHo -%g- - . *-ILy 61 ; Product (A) of the reaction is :

^
(a) propanol (b) ethanol (c) butanol (d) pentanol
7. talff-+ . Reactant (A) is :

oo
il ll
oo
ilil
(a) CHs -C-(CHz)s -C-CH3 (b) cH3 *c-(cHz)+ -c-H
oo
illl
o
il
(c) H-C-(CHr;s -C-H (d) CHs -C -(CHz)+ -CHz:OH

o CHs
ill KoH' Hzo ,
cHs -c -cH, - i -cHo (A); ProductA is:
I

cHs
o o o

(a) dr (b)
A ,rry
o

s.
$.*h,,it),
t
; ProductA is:

o o o

(a)t (b)t^ (c)

10. The reaction,

o::: + heat
conc. NaOH ----------), products Identify the product.

aq::::l: c)@o
(c,q::: ' (d,q:::
L1. Compare enolateA with enolate B.

q
o
A-
.i.,,
A
+-
o
B
Which of the fu*lowing statements is tme ?
(a) lt is more stable than B (b) a and B have the same stability
(c) E i rnoru $ftbh than.A (d) lto comparison of stability can be made
1,2. Benzalacetone is the product of mixed aldol condensation between
benzaldehyde
(CoHsCH = O) and acetone [(CH3 )2C : Ol. What is its structure
?

(a) C6HsCH = cH[cu, (b) C6HsCH = C(CHg )z

"ilo o
(c) C6HsCCH = CHCFtrg II
(d) CoHsCH2CCH = CHz
13.

(a)
ho

*,"\})

(c)
m
Product (B) is;

o o
(a) (c)
0o (d)
Oo
 o
I
- cHs the reactant (A) witt be
18. ral-ffo-rrr-1fl_+ryt :

ct{z

,"rd ,rrd ,.rd

Identify the principal product of the following reaction?
(d)
0
15. .:.
cH2cH o
-
ethanol, water, heat
20 +?
cH2cH o
-

frleE(:: :: cb)

(d)Oe(:
17. Which one of the following compounds is the best choice for being prepared by an efficient
mixed aldol addition reaction?
oHo o

,oGl.,,h
cHg cH20

o oo
,F\ ll
(dl
F\. ll I,l

,,
\_/-cH2ccHCH3 UFccH2cH2cH
HO-C-CH3
I

cHg
18. Identify the major product P in the following reaction:

oLi oLi

M*,ffir
 cH3cH2o
(a)cH3-t'r&or, o)
Mo,,
(c)
OEt
,.ru::
cH2 cH3
-
19. The enolate ion that reacts with 3-buten-2-one to form (I") is :

o o

(a) "L. (, o) ,.rtk

t4

20..
cHs
YY IH
base
(A),(A)

- reaction is
Product (B) in the above :

(").rr#, (b).1,1rS
Br
o 14- O
(d)
J>](,
(c)
il
t-t
o
il
21. H - c o j3,(s0%) product of this cannizaro reaction is
- :

(a) D-CO, +CH2DOD (b)H-Co, +D-Co2

(c) D-CO, +CH2DOH (d) o-CO, +CHDTOH
22. An organic compound with the molecular formula C9H1gO forms a 2,4-DNP d€rivative,
reduces Tollen's reagent and undergoes Cannizaro reaction, on vigorous oxidation it gives
l,2-benzenedicarboxylic acid. Structure of organic compound is:

a
,r6 ",orcHo
CHO

,,otr, cHo

o o
il lt
23.
-C-CH2-CH 2-CH24H2-C-H
CH3

I *o,
+

Number of intramolecular aldol condensation product is :

(a) 1 (b) 2 (c) 3 (d) +

24' + (c)
#r),--#k-(B)
Compound (A) exist in geometrical isomers and (B) gives Cannizaro reaction.
(A) will be :

cHs
I

(a) CHs CH-CH3 (b) (cH3)3ccH2

-CH-C-
I
-cH -cHz
cHg
cHs
I

(c) (CHg)sC-CH:CH-CH3 (d) cHs

-c -cHz -cH:cHz
I

cHs
{,ffi*l*i,i*rri+,rilii+:L1ffi,ifi+litil,lil*rgrrl+lrrffi*191i+f++il# ffi* ,

25.. Which of the following compounds will not undergo Cannizaro reaction, when treated with
500/o aqueous alkali?
o
(a) Ph-c-n *, q,n-cHo
il
(c) MezcHCHo (d) Ph -_cHz-cHo

ll
H-c-n ,,,r^- ll .^
26. '"o- rH-.t-"o-+cHrD-oH
Above reaction is known as :

(a) Cannizaro reaction, Disproportionation reaction

(b) Tischenko reaction, Disproportionation reaction
(c) Cross Cannizaro reaction, Redox reaction
(d) Tischenko reaction, Redox reaction
cHz

22. I
.->.cHs
I +
ll
cH 'o-
(Conjugate- addition)
, (A) ; Product (A) is :

I
I
c-o
I

(b)
oQ o

(d)
O? o
CHO

28. t"*u'o*u ,(A) ; Identify product and name of reaction.

do'
o

t"]
o# , Aldol condensation

(b) qn , Perkin reaction

 (c)

(d)
d
-,a''.--/
LO I
o

CH
-
, Cannizaro reaction

CH
-
CO2H

, claisen-condensation

29. Choose the most reasonable reaction intermediate for the following reaction.

Ho1/o
v_ffi q
A

frlk G)r o

(c) (d) None of these

oHo
30.
lll
CH- CHz C- H G) A \a2co3 > (B)
CHs
- - rI=
(Retro aldol)
;3HCHO +
40'C @2ok)
Product (B) of the above reaction is :

cH2
tl - oH cHo
(a) HO
- CHz
-C -
CH2OH G) uo-cHz-c-cHo
I I

cH2 oH cH2 oH
- -
cH2oFi CHO
I I

(c) Ho-CHz-C-CH2OH (d) HO

-CHz -C -CHz -CH2 -OH
I I

CHO cHz oH
-
31. CH3CH-CHCHO o,E, , o rA;ProductAis:
"o,,#S,ol,,o,'
(a) CH3(CH:CH)3CHO (b) CH3CH2CH2(CH
-CH)2CHO
(c) CHs (CH2CH2)s CH : CH CHO (d) none is correct
-
32. B.G)and (B) are isomer : Identify (B).
#
(A)

,",&
o o

o
o)
$o

,\
(.)[-{ (d)
O
33. n""*ral -s--rrl--s-*,t,), ; Product (C) is :

o o

(a)
d (b) A
(c)
a o
il
c-cH3
(d)
e( CHO

HCI/heat , A. product ( A) is:

3,4.

o
il
(a) (b) Ph - c -cH2 -cH2 - Ph

(c) Ph -CH = CH {H -Ph(d) (d) Ph-CH: C: CH-Ph

I

OH
 o
il
-^-/C-OCH3
(u)lO,l
...$corH o)l6rco2H
..9CHO

-.YrrCO2H
c.l[6(cHo (o L9 t co2H
\4cso

NaoH
36. , Product; Product is:

37. (P) KOH

A
KOH
(a) ---------+
&o

Ph-cH2-oH + Ph-co?
A

(R) o, ,P * Q Structure of (R) is :

(a) Ph-CH: CH-CHg (b) Ph-cH-cac"'

-cHe
CH" CH"
l"
(c) Ph-C: CH-CH3 (d)
l"
CH3-C: CHz
 ffi$',i+ii1i,t,
38. The following reaction gives:
CHO

+ HCHO conc.NaOHr,

OMe

cH2oH

+ cH3oH
"'qoMe+HC.B
OMe

COOH

99.
OMe
OMe
+ HCOOH (d)

o
OMe
+ CHrOH

Which of the following is not the product of an intramolecular aldol condensation ?

N ,,,0
o o

(a) (c)

oe
x =oo. of compound better hydride donor than ph-{
I

,o. -Oo
I

H
A
o"
(a) r\O (b)

(c)
. CHJ
41. Choose the reactant whose aldol reaction would give jasmone.

A
HO"
4
heat
(aldol reaction)

o oo
1"1 rut

o
(c) (d)

42, Compound Xundergoes the following reaction sequence. What is the structure of compound
x?

NaOH Heat H2lPd . 1.LiAlH4

2H2O

"#',:'.

rulHo* culHo*
(c)

43. Predict the major product of the following reaction sequence

o
o

NaoH
Hsc
A
;Iro, '' V ,
dcHs+ Heat 2.H2O
 cHg

CHO Ho
(A)
CHO -sYqE--, -A
-+ (B)
Cyclic product

Structure of (B) is :

,,,qffi:ir,,d'o
"'&--:3: "'diffi:5,
L-y
1. (a) 2. (b) 8. (a) 4. (b) D. (b) 6. (c) 7. (b) 8. (b)
9. (b) ro. (c) 11. (a) 12. (a) r.3. (a) 14, (b) 15. (a) 15. (b)
17. (b) 18. (a) 19. (c) 20. (a) 2,-. 22.
(c) (b) 23. (c) 24. (c)
25. (d) ?,6. (a) 27. (c) 28. (b) 29. 30. 3L.
(c) (c) (a) 32. (a)
39. (c) 34. (a) 35. (c) 36. (b) 37. 38.
(b) (b) 39. (c) fhe)f
4t. Ql l'*z' (d)
:rJ re-l 44. (a)
___ i
t
i
ry
Mechanism ofCannizzarois rea€tion of benzaldehyde is

'
o G-oo
nnll-rr-*[-ph , ph-[- o"
,,t l :,,,,1i1r}*.,.r,
srow
Fh;.,C
',,,;',,.,1
#dr.
* Ph -CHz -: O-
tt
tl--

,l,,:l ,,,,,.,i..,i

H
I:
o-H H : -Co! + Ph-cHz-oH
ph

A. Which of the following reactants can undergo Cannizaro's reaction.?

o
il
(a) H-C H (b) R3CCHO
-
r.)lll
-oAcHo
(d) All of these

B. Order of the above reaction is:

(a) 1
(c) 3 8l i
C. Which of the following is best hydride donor in Cannizaro 's reaction?
CHO CHO

(a,o (b,+
OMe Noz
CHO CHO

(c,o (d,o
cHg CI
D. Cannizaro's reaction is:
(a) Reduction (b) Disproportionation reaction
(c) Oxidation (d) Ion - exchange reaction
E. Which of the following cannot undergo intramolecular Cannizaro's reaction?
 oo oo
R lllijirl+li ! ii!;tiJ:iiiilij{iii:,ii

ilil
(a) H-C-C-H (b) H-c-c-Ph
oo oo
ilil
(c) Ph-C-C-Ph
ilil
(d) H-c-c-H
2. Aldol condensation proceeds by carbon-carbon bond formation benrveen an enolate donor
and a carbonyl acceptor. For each of the following aldol products (a through e) select a
donor and an acceptor compound from the list atlhe botiom of the page (ompounds A
through H). Write the letter ding to your selection in the a iate answer box.

CHO
./\
(A), cnrlo (c)
L ll
cHo (D)Hzc
- o

o
G) [ ,f ,
..V G) *r.{::':':' tcrllA.", r")}_cHo
*CO2C2Hs
A. What is the molecular weight of a compound that undergoes an aldol self-condensation
reaction to result in a fthydroxy ketone with a molecular weight of 144 ?
(a) 7o {mol (b) 72 g/mol
(c) 74 g/mol (d) 76 g/mol'
B. The aldol self-condensation of acetone is an equilibrium that favours acetone over its
condensation product. Which of the following experimental modifications is most likely to
shift the position of equilibrium toward Product A ?
(a) Using only a catalytic amount of NaOH
(b) Using only a catalytic amount of acetone
(c) Removing Product A as it is formed
(d) Increasing the reaction temperature to the boiling point of acetone
C.' Based only on observation 1 and 2, which of the following compounds could have been
ProductA?
O OH

(a) CHrCH CH2CH2CH,CH2CH3 (b) cH

illcH cH cH 2cH 2cH
3c 2 3
I

cHs

(c) CH, CHCH 2 -O -CH2CHzCH3

-
D. When a drop of Br, in CClo is added to Product B, the resulting solution rvill be :
(a) colourless, because Product B does not contain a carbon-carbon double bond
(b) colourless, because Product B contains a carbon-carbon double bond
(c) red, because Product B does not contain a carbon-carbon double bond
(d) red, because Product B contains a carbon-carbon double bond
E. Which of the following compounds from the passage will give a positive iodoform test ?
(a) Product A only (b) Product A and Product B
(c) Product A and acetone only (d) Product A, Product B, and acetone

O,;
A + C s'Kffi , Benzyl alcohol + salt of benzoic acid

CH
HCN

o*,Hgon
A. Structure of A is :

(a) HrC : CH CHO (b) Ph-CH:CH-CH,

(c) Ph-9:CHz- (d) Ph-CH:C-CHs
I
I
CH, CH,

B. Strucrure of (B) and (C) differentiated by :

(a) Tollen's reagent (b) Fehling solution

(c) 2,4-DNP (d) NaHSOs
C. Structure of E is :

*,H"
OH
(a)
HOv

OH Me

,,r7" ,,q{"
 fiEtlcfitoiir :., .

SI'B.T ECTTVE. PROETEHS

1.
o

OH
H\
OH

\ ,\,^,-on oHH \r-

o

I
OH
(A) (B) (c) (E)

O O OH O OH O ,,
Ho&g
,,;

-it -.-\ ro\,,4

(F) (c) (H) (r) U)

X = Number of compound obtained by aldol reaction

Y = Number of compounds react with NaHCO,
SumofX+Yis
2. In the scheme given below, the total number of intramolecular aldol condensation products
formed from 'Y'is :

1. O" 1. NaOH (oq)

Y
-------=-\
2.Zn.H.rO
----iL------\ Z heat

3. CHs
o
ll,,^-l
C-CH3 x HCHo*nA
Ho-
+
flc-ttro'
- los
HO-I
I
HOJ
x = moles of HCHO consumed.
Value of (x) will be
oo
il ll
4. CH.
-
C-- CH3 + CH, - CHz- C- cu, --I9{99l-+txl
X = flurrber of aldol condensation product (including stereoisomer).
Find out the value of (x).
 l. A-d; B-ci'C- a; D- b; E-c
,. a-Doilor= C,Acceptor - C; b-Donor: E,Acceptor: D;
c- Doflor = B, Acceptor : A; d - Donor : G, Acceptor : G; e - Donor : F, Acceptor = B

tr A-bB-c;C-d;D-b;E-d
L A-b,B-b,C- c

srftdrkoblems
l.'6 2. 3 3.6 4.9

,',1:. )
 tki !

1. Identify C in the following sequence of reactions :

,z:r.lcO"H socl2 >A NH'>t-';p-'c(c8H13N

U,,,r/cHs

,,,[Ton
V""ltcHa
,0, lT*
\,,/""1/cHg
(c) t'lcx
\,/-cHs
(d)

2. Saponification (basic hydrolysis) of CoHs yield :

tli@C\will
L@: mass - 18 isotope of oxygenl O
o o
(a) C6H5
il
C- @- +H@CH3 (b) CoHs
il'
- -C-O-+HOCH3
(c) C6H5CO- + H@- (d) CoHsgO- + HOCH3
il li
o a
o
ll
Cl
//-V,C-
s. I\,/ I 0"c,2h,
Yl'*| (x)
'9;HY;,f,:.1:1,
|l ri+
f,::r J ::rr:r,:: ..:::. !: : ...::'i_':: :,,rr:l:i':: :1:.;:; .:il

Product (X) of the reaction is :

o OH

,nt,ANa*"
I

(a) \M'
(, *,eJ-i;;"'
H o
I lt

(d)eJ-c-H
(c)
el-*;;*"'
4. \tVhich of the following is the correct order of decarboxylation of B-keto carboxylate anion ?

CI Noz CN
(a) (b) (c) (d)

(a) a >b>c>d (b)c>d>a>b (c) c>d>b>a (d)d>c> a>b

o o
ll il

5. + CH3 - NHz ------) Product of the reaction is :

(a) o (b) Ho cHs

,.,fitTn
v\tr-NH
(d)

o
6. Which B-keto acid shown will not undergo decarboxylation ?

,,1
c(:",, (b)

o
il
(c) ph - 8- clz -co 2H (d) cH3 -c-CHz -co2H
 7. Choose the response that matches the correct functional group classification iivith the
following group of structural formulas.
H H

"\:r"
I I

(a) Anhydride Lactam

er" *"
Lactone
(b) Lactam Imide Lactone
(c) Imide Lactone Anhydride
(d) Imide Lactam Lactone

OH

(i) Et-r,i(s-eq.) (P)

8. , ; Product (P) of the reaction is :
-^.o2H
\,/ 12; H*, Hro (650lo yield)

oH 9H ?E, oEt

,",
oft;',0, eft",., e#i,',.,
o
oi$:'
s. )\, # (x)+H,o
oH 89-91% yield
(Lactic acid)
Product (X) of the reaction is :

o
o
,/-\ \AO,
(a) I
(b)\A"-
-o OH

r' o o
t"*oA (d)YV
OH OH

MeO. OMe

to. ,,ora$CorEt
Ilr. "rf. , Al , product (A) obtained is :
(,

o o o o

,,#" (b)
o ,.,fco2Et ,.,#co2H
11. Which of the following acid on heating gives geometrical isomers as a product ?

OH
(a) CHs -CH -CO2H

(c) CHs
I

-CH -CHz -CO2H

'o', fri:il
(d) All of these
I

OH

MeoH
,A ocl' ,B M.NH'
,c; product (c) of the reaction is :

o,q.---Me
ll
o o
o o

,.,[#*"
\,AFoMe
(d,@:_:,,
o o
lt

13. LiAlH4
>A PCC
)B NH2-NH,
)c, product (c) is :

@f"
o
ooH
,",Of[,,,@i ,.,6$t r\rr Y
(d)O(;
I oH
qla
.r4. -coz )A - HCr >, aqKoH
,c. product (c) is :
4}."
CI
o OH
il I

(a)'CH3
-CHz-C-H G)MoH
o
(.I,ArH to'.r^.r,
 K:f,3'
+R - cHz -NHz THF , tal
iyr,l

In above reaction identify major product (A) of the reaction:

,"rn curQoH
Y.-cH2-R
o
Y--cH2-R
o

carQo"
Y*-*
o
16. An optically active compound .X has molecular formula C4HBO3. It evolves CO2 with
X reacts with LiAlH4 to give an achiral compound.
.X is :
NaHCO3.
(a) CHgCH2CHCOOH (b) CH3CHCOOH
I I

OH Me

(c) CHgCHCOOH (d) cH3CHCH"COOH

I I

cHpH OH
o
il
17. CHs -C-O -CHz -CHs + H- @- (@ = O18 ) One of the product of the reaction is :

o --+
il
(a) CHs -c-o-H (b) cH3 -cHz -@ -H
o il
il
(c) CH3 -C-@- (d) cHs -cHz -@'
o
ll
COCH"CH"
l'J

L8. CH"CH,OCI g-
--.: Hro* PClq
' LiAlH4 t n*14--17g1
r - ll:AfiocH2cHs
-COCH"CH, -+---:l--1----ii-
o
Product (X) is :
 (")/,\ *ro .,Q ,orfu
19. Identify final product in the following reaction;
CH3cHCooH --A--, Product
I

OH
oO,o_a,cu, o
lt
(a) I L (b) CHz : CHCOzH (c) CH3 co2H (d) cH3cH2oH
HrcAoAo -c
20. Select the final product from this sequence of reactions.
NaOEt CH"l NaOEt CHaCH,CH,BT

O CHs cHs
ill
(a) H:C -C { (b) H3C { -CH2COOC2H5
I

-COOCzHs
I I

CHFHFH3 cHFHfH3
H CHs
I I

(c) H:C -C -CH2COOC2H5 (d) cH3co -c - cH2cooc2Hs

I I

cHfHfH3 cHs
Et ,CO?CH,
4
_ CHs

Lt"
\_-/ '

H2O, H2SO4 r d\
21. neat
.
Product (A) will be :

corEt

h
o o o

(a)
co2H
-,
(b)

(i) Na
(c)
A. (d)

22. CH2(CO214e)z + ? O*.."--+CH(CO2Me)3

Which of the following reactants will complete the above reaction ?
(a) CH2(CO2Me)2 (b) (COzMe)z
(c) Cl -CO2Me (d) cocl2
23. Arrange the following in order of increasing reactivity (least-----+ most) towards nucleophile

ooo
il ilil
il
cH3c ocHCH3 cHsc cl cH3c NHCH3
1 2 3
(a)'1 <2<3 (b) 3 <7<2
(c),1 <3<2 (d)2<1<3
 : I r;i:iir 1:;}: ilii l:ii

glven.

o
,r.0co2cH3 -j--+ rr.0A-*r-.r,
(a) H3O*; SOCI2; CH3NH2
(b) Ho-/Hzo; PBr3; Mg; Cor, Hso-; SoCl2; cH3NH2
(c) LiAlH4; HzO; HBr; Mg; CO2; HsO*; SOC12; CH3NH2
(d) None of these would yield the desired product
25. A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition
of:
I +oH
ll
(a) H3o+ to cHr{ NHz (b) H2O to CH3C NH2
+oH +oH
il
(c) Hso* to cHr[NHz (d) HO- to CHTCNHz
26. Which reaction is not possible for acetic anhydride ?
oo
ll il
(a) (CH3C )zO + 2HN(CH3 )z----+ CH3C N(CH3 )2 + CH3COz + H2 N(C Hs )z
o o
il il
(b) (CH3C )zO + CH3CH2OH--+ CH3COCH2CH3 + CHTCOTH
oo
ll ll
(c) (cHgc)zo+c6H6 Alcl3
^, >cH3tcoHs +cH3co2H
- oo
il ll
(d) (cH3c )zo + Nacl-----+ cH3c cl + cH3co2Na+
27. All but one of the following compounds react with aniline to give acetanilide. Which one
does not?
O

GNHz+Grv,lcH,
Aniline Acetanilide
o
O O

(a) CHsC
ll

-Cl rul HrcAoA.r,

(c) CHgC
o
lt
(d)
,R?
-H t/occH3
28. Which of the following best describes the nucleophilic addition step in the acid-catalyzed
hydrolysis of acetonitrile (CH3CN) ?
 ,,,tDC35,
o
",rDeBH
o o

(d)Oq:b
o
30. which of following acid remains unaffected on heating ?
(a) malonic acid &) maleic acid
(c) Fumaric acid (d) Succinic acid

31. g. }g. + CH2(COrEI), -#-- ryclic product

At which value of n the formation of six membered ring takes place ?
(a) n:2 (b)n:3 (c) n :5 (d)n:6
o
_1t
s2.
q-e -r4*S-----=--product orthe reaction is :

o NHz

(a) ( 7CH2OH
\-CUTOU .,r0
,.,Q.e
OH

OH

33ft:3"H (-CO2 ) (-Hzo) , Product of the reaction is :

\-Aco2H
s4.q/co2H ---:--=-=---+ (A) (i) EIOH, HCI
(ii) EtMgsr
(iii) H*/a
Product (A) of the reaction is :

cHs
corEt
(a) orQ-r'o'Et
Et
o
il
o

(c)qrg_.n, ,.,%:-cHg
OH

cHz-o-coR
I

35. CH - O - COR2 + 3NaOH --) (A) + Salt of fatty acid (soap)

I

cHz-o-coR3
Product (A) of the reaction is :
(a) Ethylene glycol (b) Glycerol
(c) Glyceryltrinitrate (explosive) (d) Cumene hydrogen peroxide
no- ,
36. CH3 -CH - OAc Product of the reaction is :
I

Et (d=dextro rotatory)
(d)
Et
I

-oH
I

(a) cHs (b) cHs -cH (c) cH3 -cH -oH (d) CH3 -C =CHz
1ll-o, Et Et
I

cHs
0) (d) & 0)
o
sz. ph -cH = cH-l -o - n -#-H ,o, , product (A) of the reaction is :

t-
oa o

o
 o
iI
38. Ph -C-Crl + (*) ----) ; Identify the product (A).
,t*),
J
(Morpholine)
Oa o
(a)
ll ,-.
ph-C-o\_rN-H ll ,-.
(D) Ph-C_N O
\_-/
o o
il //-o
(c) ph-c-*i_)
lt
(d) Ph - C- NHz

Be. ryo*t * , ,,/on 9""ds1 MeoH

cio
Above reaction is an example of :

(a) Esterification
(c) Hydrolysis
^(t**
(b) Saponification
(d) Trans Esterification
40. Which of the following is an intermediate formed in the reaction shown below ?
o
il
CHs - C-Cl + NH3 ------J Intermediate -------+ product.
o
il
(a) cH3 -frn, (b) cH3 -c@
OH o-
(d)
I I

(c) Cl -C - Cl cH3 -c - cl
I I

oNHs eNHs
o

"r\.
41. -\,
r) NaOH. H"O
^ "f 100,c
oo (several hours)

(Principal component of coconut oil.)

Product is obtained in the above reaction is :

OH

(a), R -CO2Na (b) (c) Both (a) and (b) (d) None of these
^,n-. OH
OH
42. The reaction of sodium acetate with acetyl chloride proceeds through which of the following

'oooo
mechanisms ?

il _,/-\, ll ll - ll
(a) cHg -C-o' + cH3:t-qy. 1u) cH3-c-o..=-,GcHg-.-qy
 tt

(c)
??)fl
CHs-.-o.. + CH3-C-Cl (d) CHs-C-o--.,a1-CI,
r
o

\/ \-z
43. Which is the major product of the following reaction ?

? Hzs
CHs -c-ct ,product

OH o
il
oo
ilil
(a) CHs { -Cl -c-sH
I

I
(b) cH3 (c) cHs -c-cl (d) cH3 -C-s -C-cu,
SH
44. Which is the major product of the following reaction ?

4,
I )o +cH3 - NHz -5 product

-\

,",\,
I o

-cHg G)\o
/.'-vrr3
.N _ CH.

oo il
(c) HO -C-CH2 -CHz -C-NH -CH3
oo
ilil
(d) cH3 - NH - C -CH2 -CHz - C- NH - CH3
45.Ethanoicacid+3.methy1-1-butano1#(A);Compound(A)is:
H2SO4
o
G)Ao.^-.^-.
o
(d)
AoA\./
il

4G. q> P.ls >(A) LiArHo

>(B) PCC >rct-f--+rot
il
o
47. Which of the follorving compounds will undergo decarboxylation on heating ?

oo

(a) 2 and 3 (b) 3 and 4 (c) 3 only (d) 1 and 4

48. Which one of the following is not an intermediate in the generally accepted mechanism for
the reaction shown below ?
oo
ll p^qo. ll
cF3toH+cH3 cHcH, -3&--cF3tof, cH3 +H2o
cHs

'oH
tr4.
:O:-
ll.. | ..
(a) CF3C - OH o) cF3q - gcH(cHs)z
I
:QH

:ou :oH
1.. 1..o.cH(cHs)z
(c) CF3Q
- -O.CH(CH3)2
,l'QHz
(d) .tr? -
:QH

3eq.EtOH
49.
Ro ,//\.
co2H ,#,I|?LHlL,,
(A); ProductA is :

(a) RO CO2R (b)

,4.. corEt
Ro
o
,4..
(c) EtO COrEt (d) n-o-C-O-Et
il

50. Identify the compound C in the following sequence :

(CHs )2CHCH2C = N HCI' H2o > compound A 1' LiAIry4 compound B

>
2.H2o

c
-#-comPound
 o
lt
(a) (CH: )2CHCCH3
o
ti
(c) (CH:r ) 2CHCH 2C H (d) (cH3 )2CHCCH2OH
51. What is the final product (B) of this sequence ?

ltr----) *t* ,
A '' B
- light 2. H3O+, heat

cHs cH?co?H

(a) (')d.o,u,(o)d
SZ. Which of the following undergoes decarboxylation most readily on being heated ?

(a) (b)

(c) HO.. (d)

OH

53. What is compound Z ?

NacN
CH3CH2CH2BT rr-H--r-!1S4L-z
o
ti
(a) CH3CH : CHCOH (b) CH3CI{2CH2CH = NOCHzCH3
o
ll
(c) CH3CH2CH2CH(OCH2CH3 )z (d) cH3cH2cH2cocH2cH3

54.
-r:+- (A);
CNtl.o@/L- - -
Product (A) of the reaction is :
;N
]N
o
 (d)

o
55. CHs -CH = CH -CHz -CO2H- (D (major); Product (D is :
^-
(a) CH3 -CH = CH -CHe G) CHs -1 =cH,
CHs
(c) CHs -CHz -CH :CHz (d) CH3 -CH =CHz

oo il
56. H-O-C-(CHz)r-C-O-H-;-product,Atwhatvalueof (n) givencompoundwillnot
evolve CO2 gas ?
(a) n: g (b)n-4 (c) n-2 (d)n-1
co2H
I

57. (CH2)n ; If (n : 4) then di-carboxylic acid would be known as :

I

co2H
(a) Malonic acid (b) Succinic acid
(c) Adipic acid (d) Oxalic acid

58. ,rro ,(A)

il
o
Product (A) of the above reaction is :

HO

(a)
co2H
(b) o
co2H co2H
co2H
 'ACIDAIIID flfgffirDff ritffis,,,,

(c) Ho co2H (d) Ho

c02H HO
HO

se
^K=,,+Ho-[-[-o-H
\.ts co2H
cis-cyclo hexane
1,2-dicarboxylic acid

Identify (A).

cozHlt-$o"
^--
60. CH, zrrr,.,A;.<
CH,
\_J
How many product will be formed when above compound undergo de-carboxylation?
(a) o (b) 1 . (c)2 (d) s

A
ctl"
lr
VA
Gl.
J\-i%
J \t" prnrrrnt nf
of the reaction
rpenrinn is
ic
,"r) -.$,--+product
(_
.

co2H

HH
lt lr
HH

(a)'ffi"
co2H

(c) Both (a) and (b)

ry
(b).,1i4 ,N"

(d) none of these

H
476
62. Products obtained in the given

*--_)
A
CO2 * x,

Br Br Br
(r:is) (rrans)
The number of possible products for x and y are :
(a) 1, 1 (b) 1,2 (c) 2,1 (d) 2,2
O
.a'{- o

63"
o ,(A)
\,/ (2) Ho_ /r12o (81v0)
(Benzyl i.rronride)

Product (21) of the above reaction is :

(a) Ph - NI{ 2 (b) Ph - cHz - NHz

(c) Ph -CHz - NH -CO2r{ (d) Ph -cHz - NH -CHO
64. Which of the follorving pair is C 2-epimer ?
(a) D-Glucose, D-Maltose (b) D-Glucose, D-Mannose
(c) D-Allose, D-Ribose (d) D-Glucose, D-Arabinose
65. Total number of enol possible for the compound formed during given reaction will be
(includ ing stereoisomer) :
o
il
CH MgBr r. CH.CH 2 C- Cl --->
3
-
(a) 2 (b) s (c) 4 (d) s

66. What is the product of the following reaction ?

A, H=o-Hre--->

W
,o,Ho$oH
\J
(c)
o o
(d)
on
noA><,
 . ,,: ] : ,
..,-i':-l:,li

,##.tril},'
l" ,,

, : I .:
.

DE*.rr#[rrvEs *7.7
OH

67. CH3 (i) KBrea , (X) _A; (f)

)H (i)H*

Hence the product (f) in the above seqrlence of reacti,rns, is :

oo OH
(a) cHg (b)

A ,0,[^r"',

(b) 2. (b) 3. 4. (c) 5. 6. (b) 4 (d) 8.

1. (a') (a') b
9. rb) lo. rb) 1.1. (d) 12. ft) 13. rb) 14. (a) 15. ib) 16.
t7, (c) 18. (b) lg. (a) 20. (a) 21. (b) 22. Ic) 23. (b) 24.
25. (b) 26. (d) 27. (c) 28. (d) 29. (c) 30. (c) 31. rb) 32.
83. (a) 3.4. (a) 35" (b) 36. (a) 37. rb) 38. rb) 39. (d) 40. d
4L. (c) 42. (c) 43. rb) 44. (c) 45. ft) 46. (a) 47. (c) 48. b
49, rb) 50. (c) 51. (d) 82. (d) 53. (d) 5,4. (d) 55. (c') 56. C

87. (c) s8. (c) 59. ft) 50. ft) 61. (c) 62. (c) 63. ft) 64,
65. (b) 66. (c) 67. (c)
1. Match the Column (I) and (II). (Matrix)
 SUBJ:E:GT:IYE FEOBLEIilS

HO2C co2H
l. HO2C co2H
A
(X) mole of CO, t;
----)
HO2C CO2H

o
(y) --
^--+
p-Keto acid
A,rnh
(Y) is including stereoisomers. Value of (X + f) will be

1. ?-p, s; b-9, si c-p, si d-r

Subjective Problems
1.8
1. In rnhich of the following reaction cyanide will be obtained as a major product ?
o o
il lt
(a) Ph -c-cH, -49},
(ii)
HeOo
(b) Ph - c-- NH, -JeQn--
Brz

o o
il il SOCI, NH,
(c) Ph - c- NIH, --&g-q-> (d) Ph-c-o-H

--ll-N!L-+ A (Major) :

Product (A) is :

OH NH-NO2 o-N

,rro ,rr?
o
(c) (d)
a
3. Which of t\e following alkene cannot be prepared by de-amination of n-Bu - NHz with
NaNO2/HCI ? (n-Buryl)

(a) l-butene O) crs-2-butene (c) trans-2-butene (d) Iso-bute4e

4. Predict the major product P in the following reamion.

Me

Me "*o, , P

(d)

oH Me

(A); Product of this reaction is

+k, :

OH

'to7u
47o/o
A will be :

(a) CHz = CH {H -CH3 (b)

I

OH

,oa (d)
A
^
 7. Which of the following isomers of CsHeNO is the weakest base ?

(a) o-Aminoacetophenone (b) p-Aminoacetophenone

(c) m-Aminoacetophenone (d) Acetanilide
8. Rank the following compounds in order of increasing basic strength. (weakest -+ strongest) :

o 5*"'d'
NHz CH2NH2 NHz
t-

1 2 3
(a)4<2<1<3 G)+<3<0r.,
(c) 4<1<3<2 (d)z<1<3<4
9. Which of the following arylamines will not form a diazonium salt on reaction with sodium
nitrite in hydrochloric acid ?
(a) m-Ethylaniline (b) p-Aminoacetophenone
(c) 4-Chloro-2-nitroaniline (d) N-Ethyl-2-methylaniline
L0. Identify product D in the following reaction sequence :

cHs
I ^ 1. L$lyo.
)r tllr'1\n ,c
-_
KzCrzGiHzSo+ socl2 di"!hl1"lh"'
- c - cH2cI{2oH
cH:"laLH2Qheat(2mole)2:Hzo ,A ,o
cHs
cHs cHs
tt
(a) CH3CCH2C = N (b) CH3CCH2CH2N(CHg )z
I I

cHs cHs

CHs N(CHs )z CHs

ll
(c) CHTCCH2CHN(CHg )z
I

(d) CH3CCH2CHN(CHg )z

cHs
I

cH:
tt oH
1l-. Which one of the following is best catalyst for the reaction shown below ?

cH3 (cH2 ) 3 cH2Br (CH2 ) 8 CH2CN

;#kaH3

r.t,ftcH3cl corft*,
o
(c) (d)
GcHriltlcHs)sct- GNuJcu,
l,2. The major products obtained from the following sequence of reactions are :

(CH, )2CHCH2N(CH2CH, ), &- heat products

,
-tr-
(a) (CHs )2CHCH2NH, + H2C = CH2 G) (CH3 )2NCH2CHg + H2C = C(CH3 )z

:'' +
(c) (CH, )2CHCH2N CH2CH, + HrC - CHz (d) (CH3 )3 NCH2CH3I- + H2C = CHz

13. Which amine yields N-nitroso amine after treament with nitrous acid (NaNO2, HCI) ?

,.,GcH2NH2 G)H3cO*",

,rGO (oGNHCH3

;Bl HNo2
) (A); Product (A) is :

(a) cyclopentane carboxyaldehyde (b) ryclohexane-1, 2-diol

(c) 2-aminocyclohexene (d) cyclohex-2-enol
15. Choose the appropriate product for this reaction.
1. LiAlHa(excess)
^ -CN product
,/\,/ ,r{pr

(a) ./\,/ (b)

/\\,/CH2NH2

{.)AAo, (d)\.,n.'/*" I

NHz
L6. Which of the following product will be obtained in the given (consider minor product also)
Beckmann-type rearrangement ?
o
(1)NH2OH,HCI
product
(2)PCls, A
 (a)
<"p'^'*Ir-'
,r<"leQ (d) all of these

Me

17. Deamination (or) diazotization ofn-Bu-NH2 with NaNO2/HC1gives isomericbutene.

(a) 2 (b) s (c) 4 (d) s

1. (c) 2, (a) 3. (d) 4. (a) b. (b) 6. (b) 7, (d) 8. (b)

9. (d) lo. (b) 11. (c) I,2. (c) I$. (d) l#; (a) I5; (b) 16. (d)
17. (b)
 Five amine syntheses are outlined below. In each reaction box enter a single
letter
1. of the page.
designating rhe best reagent and conditions selected from the list at the bottom
k ,cHz-cH2-NH2

ffHa Second step [--l

Second Step [---l

rhird Step f---l

Second Step [---l

N(CHr)z

ry*o' Second s,"p []

Step [-]
A*Y
First
Second Step [--_l

Fourth step f--l

(i),:LiAlH*,inetheri .',i',,.' (ii),H'&.,base

c2HsNHz{cat- H(1}}

fia€Nli$'ratredh

il'$.Nittid$ii'#ffi
N$[3,,i*.aleohol
(CHiCo),1O,& pyrldine

rffii
1. A-c, a orc, d; B- b,d,f; C -h, d; D_d, i ora, i; E_e, a, h, a
 $ffi $

NHz
BrzlKoH ,
Product;

(a-hydroxy amide)
Product of this Hoffmann bromamide reaction is :

o OH
il
(a) Ph -C-CH3 (b) Ph - cHo (c) Ph- cH< (d) Ph -cHz -NHz
Noz
oo
z. ,rryNH2--5eBr--+ (A) o--+(r). compound (B) is:
o
(b)

o
cHg
,o,oAo*,
3'q. KoBr , (A);
Product (A) is :

,,,@fi",rw (.)q, ,.,o7

oovo
OH
*\.rJ
4. H2so4
> Product and name of the reaction is :
eO
o o
il ll
NH-C-Me NH-C-Me
(a)
(Horrrnann I
(Beckmann
-ka
\-.V bromamide reaction) O) L -, -, I rearrangement)
^ka
(., reaction) (d) None of these
Wt*,ar.,,us
NHs
5. (x)C4H7oCl )C4HeoN*-aH3CH2CH2NH2i Compound (X) is :

,u,d., I
cHgr
fl
*,.r')c-cr (c).,)o, (d)o&Ho
6. \rVhich of the following will not give Hoffmann bromamide reaction ?
oo
il lt
(a) CH, - C- NHz (b) Ph - C- NHz
o o
il lt
(c) CHs - C- NH - Br (d) Ph-c-NH-Ph
OH
(1)
+(xl-(2) Naou
^--> =o, Reacrant x is :
H*

(a) CH:CI (b) cH2cl2 (c) CHCI g (d) ccl4

 *'8-n
il

8. -ffirol product (A) of the reaction is :

d.-6tr
o o[8
il
(a) Ph-NH-C-Ph o) Ph-NH-[ -nn
OH
I

(c) (Ph)z { -NH2 (d) Ph -cHz - NH - Ph

arraarnn oh..a""
\ ll -\>-\ >u)'
u.sq.. ll ksq\
t
9.
4*-o, ,,i-o" '\>)
Product (A) & (B) respectively in the above reaction are :

oooo il[11 &)

ii
(a) ph-C-NH-CH3, pn-e-NH-CH3 CH3 -e-NH-Ph,CH3 -C-NH-Ph
oooo
liil[ll
(c) ph-C-NH-CH3, -C-NH -ptr (d) CHs CH3 -C-NH-Ph, Ph -C-NH-CH3
KoB' > (A) . Product (A) is :
10. NBS
o ooo
---lLoH JLoo -\^
I ,fo r-{..,.
ru) L-NH, tu) l_NH, r.) (d)
!,NH
oo
Ph

1r. cnsR
, NHZ
NaoBr t (A) ; Product of the reaction
(major)
is :

H
Ph Ph

cHrf
I I
(a1 NH, (b) CH3TH
H NHz
CH" Pho
PhtH l"
cnr-f-i
rll
(c) ral - oo
NHz H
 _+____)
(1) CHCIs/NaOH
(2)H'
(A)
(Major)

ocH3
Product (A) is :

OH

(a) (d)

ocH3 ocH3 ocH3

o
il
L3. R -C- NHz + xNaOH + Br2---------+ R - NHz + 2NaBr + Na2CO3 + H2O
Nui,rber of moles of NaOH used in above Hoffmann bromamide reaction is :

(a) 3 (b) + (c) s (d) 6

*-a
14. : * -O , Rate of reaction toward Beckmann rearrangement
H./
when Y : CH3CO2, Cl -CH2 -COr, Ph -SOI
(i) (ii) (iii)
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii)
(c) (iii) > (ii) > (i) (d) (iii) > (i) > (ii)
15. When primary amine reacts with chloroform in ethanolic KOH, then product is :

(a) an isocyanide ' (b) an aldehyde

(c) a cyanide (d) an alcohol
16. The reaction of chloroform with alcoholic KOH and p-toluidine forms :

(b)H3c0..
(c) Hrc-ON2cl (d) H3c+NHCHcl2
17. What is the product (O of the following reaction ?

CHFBTI
,661

d
t-BuoK

M
C1 CI

(a) (b)
 .,,-,,.'-.:,,-.- , .-,,,,,,,.Il.l,..ii,, :,, .,..,

,@tftfiiEsf r,*ltrfr),'lllFr:f,tEnftE,
CHBr,
t"
rB. -ar**, @);product (A) is:
O

19.
(a)

Which of the following reaction, does not give chloro benzene as a product
",'B ?

Ho- ,
(") fi cHCr3' Ho- >
o) n cHBrclz'

Ho- Ho- ,
(.) n cHBrzCl'
, (d) fi cHFCrBr'

20. (A) is:

Oa-##r-(A);compound

(a)

21. +xKoH
d+cHCr3 oN-c
x : moles of KOH consumed is :
(a) 1 (b) 2 (c) 3 (d) 4
22. Heating the acyl azide in dry toluene under reflux for 3-hours give a 9oo/o yield for
heterocyclic product. Identify the product (A).
*fl*
.,r1.,,,1 ,,, ,,, ,
, ,: ,'
.,'..., .,,,li,.li..:1,;..11i
':.,:: l':,,.:''i.
.rir',r, ,,,,_ ,'..,,.:
o
il
c-Ns
n"u' r (A)
toluene 9Oo/o
NHz
H
I

(,,0r:>" N
N-H

I I
H H

NHz (d)
o(\*" il
o

:l ^-aH
-\8.
@-
23. x oc(cHs )3 > (A)
Heat

Br t* l4r
(c: c )

,.,@-c:c-@ (d)Gc-cq
Br
 (1) CH2N2
24. Ho\ttu
(A) (de-colourises Br, water)
(2) acetone/H-
(3)AczO, Acetic anhydride

Product (A) of the above reaction is :

a
CO?CH3
l'

---\Agss
-\- -'-
O-
(b) xo
-.--

cHs LHg

(d) 6.6rr\' OMe

OMe
25. A rather interesting example of the Wolff rearrangement rvith 2-diazocyclohexanone in
methanol is given below. Identify the major product :

,
="roHilight \
(,
o

(")
+co2cH3
,r,5ocH3
o

(c) (d)
^.
l\iFc-o-H
ll

26. The orbital picture of a singlet carbene (:CH2) can be drawn as :

C
it
(a) rl: (b)
 (d) none of these

27. The orbital picture of a triplet carbene can be drawn as :

Hr #p
(a)riHr, .':i8ffi,,
pv
/" Dz

,-Qy'
(cr
(c-' (d) none of these

28. m -#--ral -ffi-rrl ; product (B) is :

,rr@:l
CI CI

(d)
@
zs.
Oj.*11
Select the suitable reagent for above conversion.
1a)cHrNz/L (b) CBra / RLi
(c) H2C : CHz (d) t-BUOK
 fiffiffi
iii',riai,i;:riliiiiiiii:iri'1iiii:iriiriiiiiii;iir:ii;i:ii:lii:iii::r;,ii.i::iii.:r;i;.iii i..ri;,,:ii

11Q CHzIz (2 mole),

30. HO Zn
.^4.-
(Cu) (97o/o)
Product (A) will be :

(a)Hot(no {u)HofuHo
(.)romro 161
,
crfo VM*H3
-
31.. The major product form ed in the following reaction is
Me Me

,H, + :CH2 (singlet)

-#
rurur- ''t//Me
,rr'.';Q' (b)
H
l-*
lH

Me. I
CHTCH3
(c) 50 : 50 mixture of above rwo compounds(d)
HH
.H
..N .Br
?. 'Br
32. H

To carry out above conversion reagent used in decreasing order.

(a) Na/lig.NHs , CHBrr/NaOH(A) (b) H2lPd - CaCO3, CHBr3 /NaOH (A)
(c) Na/lie.NHs , CHCI3 /NaOH (d) H2/Pd - CaCO3, CHCI3 /NaOH

FH, -ffi+ (a) + cHBr3 J

Product (A) of the reaction is :

(")q.":: *,q;:1,
o
 (1) Ho-(lmole)
3,4. , (A); Product (A) is :
(2) HO-,Brz
Noi

+ + +
(a) (b) (c) (d)
Noi
NHz Noz Noz

,,A/,-, Naocl ,

YY
35. (x ) : Productxwill be
Hp riov"r-
:

NOz o

,rrq:: NHz

co2H
Noz Noz

,.rq:::: to'*oq:;
Noz

g6. cHs
-cHz -cHz -cHz -cH, -Jl'N/o-Products
Which of the following product(s) is,/are can be obtained in the above redction.
(a) Isopentane (b) 3-Methyl hexane (c) n-Pentane (d) 3-lvtethyl pentane
o
il
37. CH3-C-NH2 KoBr
r (A) Relation between (A) & (B) is :

(B)

(a) Identical (b) Functional isomer (c) Homologous (d) Positional isomers
38. If we use py:rene (CCla ) in the Riemer-Tiemann reaction in place of chloroform, the product
formed is :
(a) Salicylaldehyde (b) Phenolphthalein (c) Salicylic acid (d) Cyclohexanol
39. When ethyl amine is heated with chioroform and alcoholic KOH, a compound with offensive
smell is obtained. This cornpound is :
(a) A secondary amine (b) An isocyanide
(c) A cyanide (d) An acid
40.. Which of the following species would not be involved in the Hoffmann rearrangement shown
below ?

e("., ef*.,
Br2,NaOH,H2O

,,,e(,,,
,r,a-k"-
\,,/ Ni-Br

,o
ON:c-o
(d) All of the above are involved in the reaction.

(b) s. (c) 4. (b) 5. (a) 6. (d) 7. (c) 8. (b)

(b) 11. (a) 12. (a) L3. (b) 14. (c) 15. (a) 16. (b)

17. (d) L8. (a) 19. (d) 20. (a) 21". (c) 22. (a) 23. (b) 24. (b)
25. (a) 26. (a) 27. (c) 28. (c) 29. (a) 30. (b) 31. (a) 32. (b)
40. (a_i
3S. (c)
kal (c) 35. (b) 36. (d)
1"1:
(c) 38 (c) 39 (b)
A. Number of moles of NaOH consumed in above reaction.
(a) 1 (b) 2 (c) 3 (d) 4
o

B. ffu[-*n, _+1-
KoH @);product (A):
(Major)
\2
(a)Ph-NHz ft)Ph-CHz-NHz (c)Ph-NH-CI{3 (d) Ph_N 'zCHg

C. Which of the following will not give Hoffmann bromamide reaction.

-ar,
o o
il
(a) CHg -C-NHz
o
,r@[-*,,
 o
D. KoBr
,(A), Product (A) is :
4*"
o
(,)
+8,*
o
(b) ql[;t', ,.,rilXi
o
(d) None of these

Given is mechanism of Beckmann rearrangement.

,A.
ffi: :,b' ---)H-vh'D
**'
,l -L
c- \ -/_. +
(r) \o" ./ { \ (il)"1 CH"-C:N
cH{ -\# I

, o
nro
Irrru
I
,i,
0
il
cHs-c-NH-Ph <#
(P,,,*
CFIr'- **
I €
OH

A. Rate determining step in Beckmann rearrangement :

(a) I (b) rr (C) III (d) rv

B.
t"'-a
: N
D
Pt',,/ \o,
On treatment H2SOa followed by hydrolysis in acidic medium above compound gives.
(a) CHa -CO2H, Ph -NH2 (b) cHs - NH2, Ph -CO2H
(c) Ph-CH2 -NHz +Ph-CO2H (d) Ph -COzH + CHs -CO2H
C. Which of the following reagent cannot used in Beckmann rearrangement ?

(a) TsOH (b) R -SO2C1 (c) BFa (d) Ph - Li

ab\
\-/ C-N
./oH
pcls__;1a;;
D.

cHs
Product (A) of the above reaction is :
::I j::iliiri,rriJi:,I jti..ii :ri

iii'itiii iu ;# [
o o

cu @-[-*,-@-.n,
cHs

3. Match the column I and II.

D.B.E. s eYen for product

aq' KoH ,1a1---El--
tnl-ffi-*tcl (Double bond equivalent)

D.B.E. : odd for product

1.*rtal-ffi-+trl

Ring expansion takes place

+oH-{-ral-!Efe-61 Carbene will formed

'Y : " .:::i::. :

6sBA,El!{8,& fiftrffiEAlE i,I

4. Match the column I and If.

cHCl3
Reimer Tiemann reaction
KOH

Reimer Tiemann expansion

(or) Abnormal RNT reaction

CCI.COONa
.............,..".J Sirurnan-smith reaction.
---.>
A

Increase in carbon takes place

5. Match the column I and II.

Aromatic compound will formed

17 KoBr> HNo"
>
------ ---'-z

-,1 >l<il Migration take place from carbon to

elecuon deficient nitrogen

o-cHcl2 =ILo39 j(A) Carbene will formed in this reaction

-q-9=9rE-+,r, -4l-c!--
6l
N0z
o
ll
NHz
N2 will evolve.
 ilr+ffi#
6. Match the column I and II:
 ---T *

"]l_ O-ffi'f* o
1. Consider the given reaction for preparation of alkyne. (Fritsch reaction).

q.:R:ffi,%*APh-c:c-Ph
Anti group will migrate because of less steric hindrance.

to:c;; @O
KOC(CH3)3
(A) ; Major product (A) is :
A (major)

->

(c) Ph-C=614-Ph (d) Ph-c:c-Ph

+ Koo@c1cHr)3 o--+(A), product (A) is :

o,h
rarM
Rate of reaction when the halide ion:
(a) Io , clo > Br@ , F@ (b) Io rBro >clo tFo
(c) F@ , Cl@ , Br@ > I@ (d) F@ rBro >clo rI@

\./
D..,,o-}6<}-.p(A)(Major),Product(A)is:(C*-f,ra1
 cH3o
crl*$ (b)

cH3o
(c) (d1 cHro

Wolff rearrangement
When ct-DiazokeJones are photo-irradiated or heated at high temperature or reacted with
silver oxide or silver salts ai room t.rnp.irtui.lirr"y loose iit
ogun and rearrrrrg*-to
u fr;;
ketene.
The ketenes reacts rapidly with water, alcohol and amines. Therefore, the reactions called

c - cHN2 4N, Ph-CH:C:O

lr
I u,o
\y-w I cH, - NHe

Ph -CH2 -co2H Ph
'll
-C H" _C - NH *CHs
o
o
il
A. on -$-cHN2 -+H-r(A),
product (A) is :

t4 74
(a) Ph -CH2-CO2H (b) Ph -CHz- CO2H
14
(c) Ph - CO2H (d) pn -co2H
o
P,?N

(A) (Major), Product (A) is:

x74
--ry--
(C:C)

ocH3
 Hhrr,. ii
C. CHr?f - C - CHN2 + CH3OH Agzo , Major product of the reaction is :

Et
Ethtt,. oli Hhr,,,
o
li

(a) Cttr?/C-C-OCH3 ral cH{/c-c-ocH3

H Et
r-Lr
t r L3rht,. O
ll

(c) Hrf-c-ocH3 (d) None of these

Et

o
ll
c - cHN2
*?o
NHs
, (A) (Major) , Product (A) is :

"'oq
- cHNe
il-
o
o

(b)m..;::ff
ll

...nsC - NH2

.,rrrt
_ NH.
ll' 'll
o o
o
il
c-NH2
(c) (d)

ll
o
N2
ll
E. Ph - C -CH2OCHg - (A) 9Oo/o , product (A) is :

(a) Ph-CH: CH-OH^+ (b)Ph - CH - CH - OCH3

(c) CHs-CH:CH-O-PH (d)CHg-CH:CH-OH

^1
cH3oH
--+ (A) , Product (A) is :
 (a)

ry
o

co2cH3
co2cH3

o
lt
G. HO -CH2 -CHz -CHz Agzo (A) , Product (A) is :
-C -CHN2 A
>

A(
o o o

oAo
(")L..,
"r0 (d)
(,

1. A-d,;B-a;C-d,;D-a,
2. A-b;B-b;C-d;D-b
3. ?--p, r, s; b -g,t, s; c-e, f, si d-p, r, s
4. ?-e,s;b-p,s; c-s; d-r,s
5. ?- p,q,s;b- r;c-p,r;d-q
6. d- q,s;b- e,siC-e,sid-p
7. a- q;b- p;.-q;d-q
8. A- a;B- c;C-b;D-b
9. A-,b;B- c;C-d;D-b;E-b; F-b; G-d
 o
ll
NH-C-CH3

I dr"'
y'v\a
clt
B

Identify the position where electrophilic aromatic substitution (EAS) is most favourable.
(a) A (b) B
(c) c (d) A and C
CI

6 (b)
o (d)

Correct order of rate of EAS (electrophilic aromatic substitution) is :

(a)c>b>a>d (b)c>d>a>b
(c) a>b>c>d (d)c>d>b>a
 \N/

3.

(a) low pH (b) Intermediate pH

(c) high pH (d) any pH
4, which of the following has the lowest heat of combustion ?

5. The product obtained from the reaction is :

,r+ cH2cr + NacN ethanol

,

(a) BrOcH2cN (b) Br+cH2cl

(c)..+cH2cN (d) Br-GcH2ct
X.*
to\
r O 1.AlCl3
>4 Zn_Hs,HCl,heat
,f _ffi_, C.
co/ Hro*

w
2.
3. Hro*
The end product (C) is :
o

(a) (b)

o o
o o
ll tl

(.) ['Orc-c6Hs

,'o
\, C _ C6Hs
il
(d)
o(:p
 '"'-r t,'tt't't,.,.,.:,
iiii
""" .
in the hydrocarbon shown below ?
How many benzylic hydrogens are present
.
7.

(b) 4 (c) 5 (d) 6 (e) B

(a) 3
ts :
8. The major product formed in the reaction

conc. H2SOa
+ HNO3

Noz

g,
(b)
Noz

The major Product formed in the reaction

is :
(c)

6 Noz

o
(c)oFl "€)
lO.IncreasingorderofrateofreactionwithHNO3/H2SOais:
o

(iii)

(c) i<iii<ii (d)i<ii<iii

(a) iii < ii< i
11.

tudtu
Increasing order of rate of reaction with Br2/AlCl3is :
OHOHO

(ii) (iii) (iv)

(a) iii<i<ii<iv (b) iv<ii<i<iii (c) ii<iv<iii<i (d) iv<ii<iii<i
o
H3CO

cH3o d",,- tt"'tol

ji?
(a) i<ii<iii.(1,, G) iv.ii .iii r.lttl'.iv<iii., iv<ii<iii<i
13. Rank the following reactions A, B and C in order of increasing rate,
Me Me Me Me
I

,^,d so3'ZH2so4> so3''7H2so4>

dso3H
dso3H,r,d
NO"
ro
so3''ZH2so4)
,.,
O s03H
(a)B>A>C (b)B>C>A (c) A>B>C (d)e>C>B
14. Rank in order of increasing rate of reaction towards EAS with bromine in the presence of
FeBr3.

(A)

(a) B<A<C (b)B<C<A

(c) A<B<C (d)A<C<B

15. 4

Identify the position where E.A.S. can take place.

(a) 1 (b) 2 (c) 3 (d) 4
 Product (B) in the above reactions is:

Noz

(c) &X Noz

q
17. p%rri. sulphonation is most favourable at the carbon number... .

@
(a) 1 (b) 2 (c) 3 (d) +
18. Arrange the following in decreasing order of reactivity towards EAS (electrophilic aromatic
substitution)
cDs

(a)a>b>c
(o)
(b)c>b>a
o(b)
(c) a>c>b
6 (c)
(d) c>a>b

,e.d
(o)

Decreasing order of rate

+ (b)
d
of electrophi Iic aromatic substi.rlr'"r r,
6 (d)

(a) a > b > c> d (b)a>c>b>d

(c) b>a>c>d (d) b > c > a> d
20. Arrange the following in increasing order of rate of Nitration:
 o6 (a)
(a)b<c<a<d<e
(b)
D
(c)

(b)d<e<a:c<b
6 6
Noz

(d)
CI

(e)

(c)d<o-c<e<b (d)a<c<b<e<d

'6'
Me Me

2r.
(a) (b)

The rate of nitration will be:

(a)c>b>c (b)a>c>b (c) a:b:c (d)c>a>b
22. The major product of the reaction is

product.
2.H20
-1-:_cxrcryZ4gb*->

\ rcn'
a,r-@
W
C-
(a) (b)
o

23.
(c)w
lt r,
(d)
w
Arrange in their decreasing order of rate of electrophilic aromatic substitution
{t n,
:

o (i) (iii)
(a)"i>ii>iii (b) iii>ii>i (c) iii>i>
24. + HO ----) (A) ; Product (A) of the given reaction is :
(4 mole) (major)

CI
(2 mole)
CI C1

C1 Ci

(d,fi"4
CI CI CI CI

25. In which of the following compound electrophilic aromatic substitution take place in phenyl
ring present in left hand side ?
oo
,",@-l-r-o o

(d)@cHz-[o

4
(,)+ + o

o
+ A nrroo ,

G)
; Reactant (A) is

(.)+
:

co2H
co2H

27.
v
Which of the following compounds is the slowest to react with nitrosonium ion (NO+ )?
O1-,.'CH3 OMe

,rrO G)o (c)

d (d)
d
 29.
reduction
*t'1 '' r(Ibuprofen)
H2SO4 Hso-
Ibuprofen is :

cHs
(a) cHs-cHz-@l"-co2H
(b) cHs
-fH -.rr@cH -co2H
CHa CHs
cHg-cH-cH3 COOH

(c) (d)

o
+
lt
9Hz
_ C--_ AlCl,
29. In.rr
cHz-cH - c-
il
o
what is the major product of above Friedel-craft reaction ?

(d)
co2H
30. What combination of acid chloride or anhydride and arene would you choose to prepare
given compound ?

-G I
c-cH2-cHz-CO2H
il
o
 o o
il il Alc13

(a) cl-c-cH2-cH-C-Cl ----#

++ I

cHs

o
,_1t
b)g H
Alcl3
+ #

(.)p +
,.-tl
L-,f"
o
#
Alcls

,.,6+ r{4 o
^cra )

31. In the given conversion best yield will obtained with :

o
lt

(A) n,"
lsL l,
(B)

o
ll
(a) A =CHs B =Zn(Hg), HCI
-C-Cl,AlCl3,
?
(b) A =Zn(Hg),HCl, B =CHs
-C-Cl, AlCl3
(c) A =CHs AlCl3, B =Zn(Hg), HCI
-CHz -Cl,
(d) A - NHz D, B =CHg AlCt3
-NHz/HO-, -CHz -C1,
32. Rank the following in order of decreasing rate of reaction with alkoxide ion (CH3CH2O- ) in
a nucleophilic aromatic substitution reaction :
Br Br Br Br

Noz Noz
72 3 4
(a)3>4>l>2 (b)3>4>2>7 (c) 2>7 >4>3 (d)+>3>2>
33. Identify the principal organic product of the following reaction.
F

+ NaSCH3 ----) product

ozN Br

(a) (b)
cH3s Br ozN

cH3s F F

(c) (d)
ozN Br ozN scHs
34. TvVhich position will be attacked most rapidly by the nitronium ion (-NOz)+ when the
compound undergoes nirrarion with HNO3 IH2SOa :

ABCD
ocH3

(a) A (b) B (c) c (d) o

NHz

conc'Hzsoo BrzlHzo
,(x) ,(y): product (y) of this reaction is :
NHz

(b)

s03H
 Br
(c) (d)
so3H

Br Br
36. A11 the hydrocarbons shown are very weak acids. One, however, is far more acidic than the
others. Which one is the strongest acid ?

(")o

sz. + 1Arcr3>,o, 3: i'?S';rrrl 1l ffiH ,r.l 6. NaH,

O ( (D)

o
Product (D) in above sequence is :
;e-*"o
cFg CF:

(a) cHs
-

(c)f
OH

cFs
38. The action of bromine water (excess) on salicylic acid results in the formation of :

Br COOH

Br COOH
(a) (b) OH

OH
Br COOH

(c) (d)
OH Br
39. What is the correct order of olp ratio when E+ attacks the following system ?

PhF PhCI PhBr PhI

A B C D
(a) A<B<C<D (b)e:B:C:D (c) D<C<B<A (d) D<B<A<C
40. How manyproducts are capable of beings formed from toluene in each of following reaction ?
Mono-nitration

N
(A)

6
,*o, \
>K-
(Bg"r t
Di-nitration
(B)
Htro" I
(110') I
.t
Tri-nitration
(c)

(a) A=3,B=$,C=B (b) a=3,B=6,C=6

(c) A=3,B=QC=10 (d)A=3,8={C=6
41, Nitration takes place at the which position of the given compound ?

(a) A (b) B
(c) c (d) D

a>(cH2- co2H Ac"o

42. ---?-'>? , Indentify the product.
VJ_aOrn
(")q.":;ccr2Ac (b)q.,:;co2H
4s. ., -
o-ra
l-9.,

I
(A) ; unknown (A) is :
-Yr_-
o
(b)9" (c)
Q: il
(d) Ph-c -Ph

6-., +CI

#-ralfrffi (tr) *to'', (c). Product(c)is:

*r+ ,,q": ,.rod

Ph
Ph

45.. The reaction of toluene with chlorine in the presence of light gives :

QHz CI

,",''Iy'' ,0,6}'' (c)

o ,r6
CI CI

46.o+--,f..,+@)_#(B),Product(B)inthisreactionis:

4z.O+U -+ suitable product of this reaction is

OA(c)o
:

,"r& ,o,o (d)

 Me

48. 5+a; Product (A) of the reaction is

O
:

CI
SH _SH
QHz SH

(a,+ (b) no reaction (c)

r5
Q
(d)

cHs CI CI

(i) NaNO2/HCI
(B), Product (B) in this reaction is :
(ii) H3Po2

Na"S
so. 2 (A), Product (A) in this reacrion is :

Noz

(b)
oS (c)
SH

r5 '-q Noz

Noz

Q
Noz

Noz

NH"
l'
51. (A
o, _>(A)
NaNoz,zHCl
Product (B) of this reaction is :

I
cHs
 OH

(a) (b)

N-N-Ph *-N@cH,
OH OH

,.r+ (d)
dn,:*@.n,
Ph
o-H
I

HNo3/H2so5
s2. I'A) (A) + (B)
\7 (more volatile) (less volatile)

Product (A) of the above reaction is :

OH OH OH NO,
lo

,,,d*o' to'd*o, (d)o

Q
(c)

Noz
NHz

-+x2tcl + 2HC1; Major product (x) in this reaction is :

(s6 - 63%)

Noz

+ HNO"
H2S04

(a) 2 (b) 3 (c) 4 (d) s

?
, the missing reagent is :

-*
(a) CF3CO3H (b) H2so4 (c) LAH (d) NaBHa
 cH30->
s6.
+ Noz Noz
above reaction is an example of Nucleophilic aromatic substitution. TyVhich of the following
halide (-X) is mosr readily replaced.
(a)-r' G)-ct (c)-Br (d)-r
57. 'vVhen comparing.the hydrogenation of benzene with that of a hypothetical 1, 3,
S-cyclohexatriene, benzene than the cyclohexatriene.
(a) absorbs 152 kJ /mol more heat (b) gives off 152 kJ/mol more heat
(c) absorbs 152kJ /mol less heat (d) gives off 152 kJ/mol less heat
58. Which of the following hydrogens is most easily abstracted on rea6ion with bromine free
radicals, Br. ?

T",T"gT"
(a) (b) (c) (d)

(a) a (b) b (c) c (d) d

59. The electrophilic aromatic substitution proceeds through a :
(a) free radical (b) sigma complex (c) benzyne (d) carbene
60. Which of the following substitution of benzene is ortho-para in electrophilic substitution and
ortho-para in nucleophilic substitution ?
(a) - NOz (b) - No
(c) - SO3 H (d) - SO2Me
61. The number of possible isomers of dichloronitrobenzene is :
(a) 3 (b) + (c) 6 (d) e

62. Which of the following is not an aromatic compound ?

63.
,,l@ o)/ri\ v2
Consider the following sequence of reactions.
,ov (d)(d
1.SOCI2 , Zn-Hg
t'fftooH
\./\cH2c6Hs l*nt ydilct7 ^^ C;;c. HEI
-) l,

The end product (B) is:

o
64. acl' (A), Product (A) of the given reaction is
Ph - NOz + Et -Cl > :

NO.
l'
(a) Ph-NH-Et (b) no-reaction ,.,&,, (d)9
Et
65. In nitration of benzene by mixed acid the rate of reaction will be :
(a) C6H6 =CoDo =CoTo (b) coHo > coDo > coTo
(d) coHo <coDo <coTo

H"SO. Ph - CH"CN
66. (A) #(B);
ErO-/L
Product(B)is:

(a) Ph-N-C-CN (b) Ph-|r]=C-Ph

I

Ph

(c) Ph-N=N-Ph (d) Ph -CH = CH - Ph

67. Which of the following ring compounds obeys Huckel's rule ?

(a) C oHi' (b) c /Hi' (c) CaHa2 (d) c4H4
68. Nitration of which of the following reactant glves maximum o/o of meta product (using
HNO3 |H2SO4) ?
(a) Toluene (b) Aniline
(c) Benzene (d) Isopropyl benzene
Br
Ph
zegBF+
> (x) zBF;; compound (x) will be :

Ph

Ph Ph Ph Ph

(c) (d)
Ph Ph Ph

o
I

zo.O ffrer
\tVhich of the following is true statement about the reaction ?
(a) Ortho isomer is major if PhONa is used
(b) Para isomer is major if PhOK is used
(c) Product formed is further used for preparation of drug aspirin
(d) All of these
71. Two benzyne intermediates are likely to be formed equally. Reaction with amide ion can
occur in two different directions with each benzlme, giving three possible products. They are
formed in a 1 :2:7 ratio. Asterisk (") refers to lac.

-'i-
Clcr ff* (A) product major; product (A) is :

IVH..
-,-/
,"rO NHz (c)
NHz

72. Which one of the following undergoes nucleophilic aromatic substitution at the fastest rate ?

,",+ o,+ ,.,+

ClCl61Cl

,.,+
NOz Cl CHg OCH3

73. For the reaction ; ? ((:, , the best combination of reactants is :

-_)
(a) C6HrBr + HNO3, H,SO+ (b) C6HsBr + H2SO4, heat
(c) C6H'NO2 +8r2, FeBr3 (d) C6H5NO2 + HBr
74. The action of AlCl3 in Friedel Craft's reaction is:
(a) to absorb HCI (b) to release HCI
(c) to produce electrophile (d) to produce nucleophile
75. n-Butylbenzene on oxidation with hot alkanine KMnO4 gives :
(a) benzoic acid (b) butanoic acid (c) benzyl alcohol (d) benzaldehyde
76. Which sequence of steps describes the best synthesis of 2-phenylpropene ?
(a) Benzene * 2-chloropropene , AlCl3
(b) 1. Benzaldehyde (C6H'CH = O) + CHsCH2MgBr, diethyl ether
2. H3O+ 3. H2SOa, heat
(c) 1. Bromobenzene * Mg, diethyl ether 2. Propanal (CH3CH2CH = O)
3. H3O+ 4. H1SO 4, heat
(d) 1. Bromobenzene * Mg, diethyl ether 2. Acetone [(CH3 )2C = O]
3. HsO+ 4. H2SO 4, heat
77. What are the products of ,h. following reaction ?
: \
/
-+
v/ocH2cH2oH -- d"
excess HBr

rJl ,r+ocH2cH2Br rul + BrcH2cH2oH

$e'
rtl + BrcH2cH2Br ral + BrcH2cH2Br
ftoH $e,
78. What is the product obtained by heating the following allylic ether of phenol ?
OCH2CH : CHC6H5

OH
o oH loHs
= GHC6H5
,r, .,
#H2cH #HCH:cHz
?cuHt
,., ()ztH2cH:cFIz (d)'o{\)-fih:cHz
79. When you ingest aspirin, it passes through your
\Jwhich has an acidic pH, before
stomach,
traveling through the basic environment of your intestine. Provide the structure form as it
exists in the intestine.
o o
lt il
9-C-CHs OH O_C_CH:
co2H CO;
-
(a) ,r,6co2cH3 (c) (d)

80. Which of the following sets of reagents, used in the order shown, would be enable for the
preparation of p-chlorophenol from p-chloronitrobenzene ?
(a) 1. Fe, HCI; 2. NaOH; 3. NaNO2, H2SOa i 4. H:POz
(b) 1. Fe, HCI ; 2. NaOH ; 3. NaNO2, H2SO4 ; 4. H2O, heat
(c) 1. Fe, HCI ; 2. NaOH; 3. NaNO2, H2SO4 ; 4. ethanol
(d) 1. NaOH, heat ; 2. HCl
81. rWhich one of the following compounds undergoes bromination of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?

(a) (b)

OH
o

82'6 il
cH3-c-cl
>(P)-_hhv#gr+(Q). Product (Q) in this reaction is :

o
il
O-Me oco Me C-Me OMe

"r6 (b)
6 (c)

o OH
(d)
o OH
 -ffiil,Ji},,rhe Product (P) will be :

,,6., ocH3
(c) (d)

ocH3 ocH3
84.
@.,, -T-r"@ :-+ QHz
NaNO2,

HCI,9O'C
(A);Product(A)is:

(a) Ph - CHz
o
-N -CH2 -
I
Ph (b) Ph -CHz-N -N
- O
I

N=O Ph

e,./cH2 - Ph
(c) Ph - cH2 (d)Ph-N:O
i=>cH2 - Ph

-+ fY.x
8s' + HCr
ry:lr,',r*NaNo2 -?\Y
H
This reaction is example of :
(a) Intermolecular C - N coupling (b) Intramolecular C - N coupling
(c) Intermolecular N - N coupling (d) Intramolecular N - N coupling
86. The total number of isomeric trimethylbenzene is :
(a) 2 (b) 3 (c) 4 (d) 6
87. Caliene, CzFo, is expected to be a fairly polar aromatic molecule. Which of the following
resonance forms contributes to the greatest extent towards the real structure (resonancE

(a,? o,t (c,? ,.,?

hybrid) of the molecule ?
88.

do
89. In the reaction given below, the major product formed is :

o
Br2(1 mole)
Product.

,rr$o
o o

Br
o

Br
90. p-aminophenol reacts with one equivalent of acetyl chloride in the presence of pyridine to
give mainly :
OH?
,rrd' ,r,ryc-cH3 (c)
C-CH"
NHz NHz NHz dll" NHCOCH3

91. TvVhich
of the following reactions can be used to prepare acetophenone ?
(a) coHo +cH3cocr--1'actr+
u (bxc6Hscoo) 2ca+(cH3coo)2ca heat '
2H2O
(c) c6H6cN ''^t!'Y,t'
2 H3Of
, (d) Allof these

92. Consider the following sequence of reactions.

1. 02, heat
C oH u + CH 3CH = CH z 6 B+C
-H'fo+-4 2. H3O+, heat
The products (B) and (C) are :
(a) benzaldehyde and acetaldehyde (b) benzoic acid and acetic acid
(c) phenol and propionaldehyde (d) phenol and acetone
93. An organic compound having the molecular formula C8H10O on being heated with 12 and
dilute NaOH gives a yellow precipitate. The expected compound is :

(a) C6H'CH2CH2OH tu) cHr+cH2oH

 (c) rr.$!o, (d)
X.r, O-cHoHCH3
94. The product (B) of the reaction sequence is :

.,+cH2Br -,l&lt2e-
a
-jffi r.
OH OH
(a) .rrlt+cH2Br (b) .,+.rrlr.r,
(c) t'ry@cH2cHCH3 (d) cHr-611
+cH2Br
oH oH

95. Consider the following sequence of reactions.

OsO, 1. HIO4
A B. The final product (B) is :
----:-----+
NaHS03 2. NaOH, heat

cHs

(,,q::::, G,ror-:H"
96" For the reaction, the product expected is :

1. MeMgBr (2 mole) product,

,
2.HrOn

,rrffi: .',o{"
Me OH
OH
o

,rq.:tr'
I

(c)

lt
o
 :i:i i. #$ffi
i i:i:ti;ii:i:r::i:,::,:.::i,a:i::::::it!t;titiiitlirtll!tt!l;i:i?i.:i1:]litti,ii:..Biif,xi:l

97. Hydrogenation of naphthalene (P) with excess hydrogen gas stops cleanly it 1, 2, 3,
4-tetrahydronaphthalene (Q). What conclusion can be drawn from this experiment ?

excess H2
Pd C (cat.)
-
(a) the hydrogenation of P is exothermic
(b) one aromatic ring of P is more reactive than the aromatic ring of Q
(c) one aromatic ring of P is less reactive than the other ring of Q
(d)reduction of the first C = C of P is faster than reduction of the second or third C = C
98. Suggest the best reaction conditions for the synthesis shown below.

o_+
(a) (1) HNO3 ,H2SO2i then (2) Br2
(b) (1) Br2; then (2) HNO3, H2SO2
(c) (1) CH3Br, AlBr, ; then (2) HNO3, H2SO3
(d) HNO3, H2SO2, then (2) Brz, FeBr3

99.

In the above compound Cl will liberated easily in the form of :

(a) cl@ (b) ct- (c) Cl' (d) c12*

1"OO. Consider the following sequence of reactions:

PhCO2H ': l,$t tA J'P+Qo' h"ut ,8. The final product (B) is :
2.NH3 2.H2/Ni
(a) benzonitrile (b) benzylamine (c) aniline (d) benzamide
1O1. Themajorproductoftheacetylationofsalicylicacidwith XcrOflH* followedbyheatingwith
anhydrous A1C13 is :

COOH COOH

OH

(b) o 1l
#ffiffiffi#11#fi+ilfjiriri#llt;,iir.i,:,,lrfi+j,r,liiri,il:i.,,r,ir,.:,'ir,.:;:

COOH o COOH
OH

(c)

102. Which one of t he following statements is True:

o:< 1

(a) PhLi adds to both compounds with equal ease

(b) PhLi does not add to either of the compounds
(c) PhLi reacts readily with 1 but does not add to 2
(d) PhLi reacts readily with 2 but does not add to 1

1O3. The major product expected from the mono-bromination of phenyl benzoate is :
Br Br

(a)
6coo€ *,Gcood
(c) ,.-@coo€ (d)Gcoo#r'
lO4. The Birch reduction of benzoic acid gives :

,,, *, (d)
GcooH GcooH,o GcooH GcooH
1O5. The decreasing order of reactivity of meta-nitrobromobenzene (I), 2,4,6-trinitrobromo-
benzene (II), para-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV) towards
HO- ions is :
(a) I>II>III>IV (b) II>[V>III>I (c) IV>II>III>I (d) II>IV>I>III
106. Which of the following tetracarboxylic acid form di-anhydride :

COOH COOH

COOH COOH

COOH cooH
(a) o)
COOH COOH

(c) neither (a) nor (b) (d) both (a) and (b)
 CO"H
l'
toz.
Of"' o
2t<t > (A); unknown (A) is :

il
C-I

(a) *,.,d:",,d:,.,'d:
1o8. Ph - NH2 + Ph3coH'*/' r-(major)
p . (not a N-derivative), product (p) is :
NHz CPh

,",&cPh3 t'dcPh3tt'd
1O9. Deduce structure of (A).
o)
d cPh3

(A) CeHro
-S&*(B) CaHso+
-*-a8HsBro4(C)
(one-product only) :

(a) ,Q ,rd (d)

1lO. The deamination of Ph2C(OH)CH2NH2 with NaNO2 -HClgives a product (p), which on
oxidation gives benzoic acid only. Identify the produci (p).
o
il
(a) Ph -CHz -CH2 -Ph (b) pn-c-cH2-Ph
oo
illt
(c) Ph-C- C-Ph (d) Ptr -CHz - NH - Ph

111. Ph -co2H socl2 >4 MezNH

,B (c) )ph -cHq unknown reagent (c) is :

(a) LiAIH+ (b) NaBH+

(c) LiAlH4(t - BuO), (d) eccTcH2cl2
 NHz NHr, NaOH
ll2. (A) - (B)
Alc13 (sooZl triethylene glycol. heat (73olo)

cH2cH3
Product (B) is :

(a) ,rrff ,.ra

?
1L3. CoHs(CHrlrt -ct-+- (A) --glq5(B); Compound (B) is :
C12H14O H3OP

,rr[A *,0]-co2H
\,/\c (cH z)+-co2H
il
-
o
o

.o(::::
il

(d,0[:)"
il
o
R R R

114.
d -€
HNO3
H2S04
d^,"'+
(ortho) + Noz
In the above reaction o,/p ratio will be highest when :

(a) R=-CH: (b) n--CHz-CHs

(c) R=-CHMez (d) n=-CMes
 (d[to'" n*o, ,,r,
goN
product (4) in the above reaction is :

o o
.:rol-[-=. NHz
ll
C-N-Et

'"' (b)
*o
I

Et

Tn, fl To, fl
,., ,0,_,^
-__^.
"frc-NH-Et
CI
rfrc-NEt'
{---
(A); Product (A) or the reaction is
116.
0l-" Br ,r,,F ' :

Br

,,,6Q *,"@,.,@,.,q
, H2so4 > major product of this reaction is
ll7. Ph - CHO . :

O
OH
I

(a) Ph3CH (b) Ph { -Ph (c) (d) Ph2CH2

I

Ph

118.d Br*Cl
(A); Product (A) of this reaction is :

(c)

H
 lvoz

1 19. ls:

(a) L,2,4-Tnniffobenzene (b) 1,3,5-Trinitrobenzene

(c) 1,2,3 -Trinitrobenzene (d) Tri-nitro toluene (TNT)
12o. f KoH/MeoH
> (c); compound (c) is:
o -ffi(A)#>(B)
o
o
lt
(a) Ph-CHz-c-{ (b) Ph - CH = CH-C -CH:
il

o
il
o
(c) Ph-c< (d) Ph
lt
-C -CH = CH - CH:

tzt' NHz-NH',(c); compound (c)

q is :

otP(A)#(B) in
(",0[:,:i
"'0[:,:i
:
,.,q:,:i ", @)-cH
cH
- Ph
Ph
OH

122.
d", (i) aq NaHCoe/boil
HsO*
, (A) ,product
(major)'
(A) in this reaction is :

(d) No reaction
 ,u\_

12i,. *o, <QX'<O),iii Identify position where attack of (Aro- )is favourable.
/ \
ii
(a) i (b) ii (c) iii (d) iv

124.
:--:p "" ,(A), Product (A) of this reaction is :

NO,
t-
,,0(:, o,o(:;'' (c, ,0,@*o,
o
II
C- Me

tzs.
6 -ffi-a.r-flp (B), Product (B) of this reaction is :

CH2-Me CH2-Me O Me cH, Me

-
t"@*o, t"@.-*r, (c)
dl
Y
,0,@*'
Me Noz
I

-cl Ncl' >(A) H.o*

\2
126. f,A] +HN = cH

Me
>(B), product (B) of this reaction is :

.,dCHO (b)

d CHO
(c) No-reaction (d)
O:C
-
Me

rzz.dco2H EtoH
H*
) (rU
lilTll
MeI
, (i) NaoH
(ii) H-
, (D socl2 ) : product
(iD AICI3

End product of the above reaction is :

 o

-ll
IL
(a)
vrs) ,rr&
(c) (d)

o
L28. cHs-cl (2mole) Ph-t'tz ct t (B)
Ph - NH2 ,1A1 (major)
Butter yellow

Product of the above reaction is :

Me N-Me Me-N-Me
-

(a) (b)
N N-Ph
-
Me
Me
lo
Me-N-N N-Ph
-
(c)

1.29. p-Toluedine reacts with benzene

(d)
6
diazonium chloride to form compound, which on boiling
with aq. H2SO4 give ......... products :
(a) 3 (b) 2 (c) 4 (d) s

130. aqNHs
r(A)-#b-+(B)ffi (c)

CI
Product (C) of the above reaction is :

r' r' NO" NO"

(E)

6 Br
Br
to'r,@r.t"q:. (d)
 (A)
-ffi-+ ,-(fJ.rr, Major product (B) of this reaction is :

OH
CH

o,d,, ,r+
Br

Noz
132. 'o- , (A) ; Product of the given reacion ls:

(c)-'"1!,o"' ,0,nol}*"'
NHz
lgr
(cH3co)2o
I'33. >(A) -ffi-+(B)-*+(c), Product (c) of this reaction is:
O
NH, NO,
t- t-
(.)[A
,",@*o, (b)

dNoz
-r,ANoz
(d)

+Noz
134.d -&l#q-(A) (major) ; Product (A) will be :

''6,.""'d""'trf"
Br Br
'0"'$"
135.
(i)HNO3
(ii) H2so4
(A) KMno+/^
, (B) socl' , (c); Product (c) of this reaction is :
(Di- nitro
product)

O:C

il
COCI Cl
-
Noz Noz Noz
(b) (c)

Noz

136. cH3-NH-cHs >(A)-dh(B); Product (B) of this reacion is :

Noz

cHe \N/ cHs cHs\.N/cH3

(a)

+NHz
(b)

cHg\.pzcHs

(c)
d^."' (d) None of these
 NHz
s"+ *"
ts7. fal -flffi(B) '
Which of the following compound on hydrolysis gives reactant (A) :

*,qj -:p
o

HNO3/H2SO4
138. ) (A).
MeO
Product (A) of the above reaction is :

tu
Noz
Noz Noz
(a) o)
MeO MeO

(c)
@ Noz

MeO
*'@-,o-i-
(d)
Noz

1.39. "' ,: Product of the reaction

cSz
is :

H
Br

t"'@*ri
I

o)@*ricH2-Br
- ,9t

,rb*i ..,q-*,i
Br
 #
OH

A"'l-,
r4o.
++*, Noz
(B)
(Paracetamol)
; Product (B) of this reaction is :

o
il
o- c-cH3
?, fl
6
OH

6
NH,

(a) (b) ,.,q[-cH',.,+

NHz
,*Y NHz oH
o

1"4r. AICI?
A) zn(a.il ,1A1--Ef9+--
O +

o
2.2 equivalents HCI
15,1
.

(succinic
anhydride)

Product (C) of the above reaction is :

ooH

+ -\-l-o._"*#P,,g,tfJ,
142.
o
Product of the above Friedel-Craft reaction is :

co2H
(a)

(.)
co2H
,.,ff
 .i,, ..' jl::.,', ',:.;., r . i'',i'rr-' I ' ' tl
':,.r 'S4l
4ftPP44$.S,,coMPouilDs
reactive towards nucleophilic'aromatic
.,4g. which of the following 2-halo nitrobenzene is most
substitution ?

Cl I
F Br

Noz
(a) .,d,u"' ,, d*o' ,0,fi*o'
144. Choose the best method to prepar: *t"tn compound
:

cHr{ cH,
/4.'
lol
-/ I

*,offi
Noz

,",O-Sffiffi
O O
(1) HNO3/H2SO4
(c) (o
"'"=----lll_,o'-n"^'" ' (2) CH3 -CH- CH2 -CI/A]CI3
I

CH:

cHs
I

r.4s.
O -ffi-,n",ifl-*,-#h-crl --ry,e,_-
(c)
-ffi-' r"i?,,,"
Benzocaine has been used as a component
of appetite suppressants, burn and sunburn
remedies. Benzocaine is :
o
il
CO"Et c-NH OEt

t"@*,
l'
(b)

d ,',dt + (d)

NHz NHz

146.ry:;"' HBr , (a) Product (A) of this reaction is

a
;
860/o
:

Br
(a)
OH
 OCH"
l"
a|'' ocH3
!47. IUI Hl(excess)
rProduct.
\,nocH3 ^
Predict major product of the above reaction is :

OHI

(a)

OH
OH

OH
,rrd: (c)
&
r48.6 H?'
HN03
, (A) (Major) ; Product (A) is :

OH OH

,0,fi*o' (c) 6
Y
Noz
149. Arrange in their decreasing order of rate in SNAr.
CI CI

Noz

+ 6
Noz Noz Noz
(i) (ii) liii) (w) (v)

(a) i>ii>iv>iii>v (b)ii>i>iii>v>iv

(c) v>iii>i>ii>iv (d)v>iii>ii>i>iv
Which one of the following compounds undergoes bromination of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?

(b)
 151. What is the product of the following reaction
?

Hzso+,
GocH3.G::.",
t"'
Q- iIr,-G ocH3 &) (cHe)2cH
ffi
c
n,G[:',$ocH3 (d)(cHs)2cHffiocH3
152' which sequence represents the best synthesis
of 4-isopropylbenzonitrile ?

(cH3)2cH+c-N
4-Isopropylbenzonitrile
(a) 1. Benzene + (CH3)2CHCI,AlCl3;
2. Br2, FeBr3; g. KCN
(b) 1. Benzene + (CHr)2CHCI,AlCl3;
2, HNO3, H2SO4; B. Fe, HCl,;
4. NaOH 5. NaNO2, HCl, H2O
(c) 1. Benzene +(CH3 )2CHCI, AlCl3;
2, HNO3, H2SO4 ; B. Fe, HCI ;
4. NaNO zlH3l 5. KCN
(d) 1. Benzene + HNO3, H2SOa
; 2. (CH, )2CHCI, AlCl3; B. Fe, HCI;
4. NaNO 2,HCl,HzO; 5. CUCN

153.
&" 1. Mg/Ether

2. HrO*
s.
+.
runoo/oH-
rl
A, ProductA is :

COOH

,",@o'
coo

(c)
6 *ro
 'ls4.
@
(",0(::).
o
I
,o0(::;
L55. What is correct order of rate of nitration of the following compounds ?

c6HscH3 coHo CoDo CoTo C6H5Br3 CoHs fr *, C6H5NMe'

A FG
(a) c>A> B>C>D>E>F (b)c>B>c>D>A>F
(c) G>A> B:C-P2E>F (d)G>A>B>C-D>E>F
rs6. .i::l ,.,. ,rx-rg*5lyr;productyis:
@
,rrd
157. Com_pound A(C7 HsO) is insoluble in water, dilute HCI & aqueous NaHCO3, but it dissolves
in dilute NaOH. When A is treated with Br2 water it is conrrerted into a compound C7 H5OBr3
rapidly. The structure of A is :
OH

,rrd *,#"' (c)

cHs
cHs
L58. Give the product of the following reaction sequence :

1. HNO3/H2SO4
2H2lPdlC
. ___) Product
3. NaNO2/HCl
-- 4.CuCN
5.MeMgBr
6. H3O+

ozH OH

159.
(a) (b) (c)

Give the product of the following reaction sequence:

HNO?/Il2SO4
1.
d (d)
d
2Br2fFeBry
3.H2lPdlC
Product
4.Cl2/FeBr3
5. NaNO2/HCl
6. KI

(a) (b) (c) (d)

160. Which represents an intermediate formed in the reaction of toluene and chlorine at elevated
temperature in sunlight ?

,ur''rftr*, (b) CHa

r.r@iu,
L61. The decreasing order of reactivity of m-nitrobrornobenzene (I), 2, 4, 6- trinitrobromo-benzene
(II), p-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV), towards OH-ions is :
(a) I>II>III>IV (b)II>IV>III>l
(c) IV>II>III>I (d)U>IV>I>III
162. Which one of the following compounds is most reacrive for ArS *z reaction ?

C1 CI Ci

6 Noz
I I

(a) ,0,@*o, (c) ror@*o'

Noz Noz
163. Which one amongst the following carbocations is most stable ?

@
(a) CoHs
-CH-CoHs
"rtr
(c) CHs
@

-C -CH3
I
(d) A
cHs

164. Cyclopentadiene is much more acidic than cyclopentane. The reason is that :

(a) cyclopentadiene has conjugated double bonds

(b) cyclopentadiene has both sp2 and sp3 hybridized carbon atoms
(c) cyclopentadiene is a strain-free cyclic system
(d) cyclopentadienide ion, the conjugate base of cyclopentadiene, is an aromatic species and
hence has higher stability

(r) (ni (Iu1 (r\r)

Friedel-Crafts acylation reaction can be used to obtain the compounds

(a) II, III and IV (b) I, III and IV
(c) I and II (d) II and III
166. The major product of the reaction is :

"'
FeBr3
, Product

,rr rr ,t,

Br

Br Br
 ;i;;";.o*,ou,'o."*,.,nuc1eophi1icsubstitutionwith
aqueous NaOH is
BrBr.
:

?n
ft conc' HzSo+ , n
'lL
Brzllzo ,,
(excess)
(/ 1oo"c

oH oH oH

,","+ ,0,"d:''qso3H (d)

SO3H Br

of reacdons :
169. Consider the following sequence
COOH
socl2 > a --Lacb--+,
lS=, +c
2'H'o*
--
CH2C6H5
The end Product (C) is :

,",0+ ,rrq
caHs
coHs
o
 For the diazonium ions the order of reactiviry towards diazo-coupling with phenol in the
presence of dilute NaOH is :

Me2N-@mj o,N@., ."ro-ONi cue@,u,

(D (II) (III) (IV)

(a) I<IV<II<III (b)I<III<[V<II

(c) III<I<lI<[V (d)III<I<IV<II
l7l. Major product obtained in given reaction is :

o+ Q, H?so4>

Qgg
.'8 "'t .,'8
r72. fi'h
\l/rol
"' ,
orAlcl3
(B) ; (A) & (B) are isomers. product (B) is :
(major)

Dewar's Benzene

,,,o .,,x ,.,+ (d)E

173. The step shown below is a recent synthesis of corannulene.

- pd/c - (A) zoHro

_C
i;i Corannulene

Product (A) is :

,rr@ ,rr@

174.

Identify the position where E.A.S. will take place :

(a) a (b) b
(c) c (d) all the position are identical

cn'
tzs. -Eo2H (i) {u''9r.-Eo-'a
,
O-
The labelled carbon goes with :

74
(a) Ph (b) Coz
-8orn 74
(c) pn co2H (d) cH4
-tou2-
1.76. compounds in electrophilic

cH2co2H |l(CH3)2

(a)
a\
U
I>tI>rurlrv
d II

(c) III>l>IV>II (d)II>III>I>[V

177. Which of the following is the major product from sulfonation of o-tetralone ?

HrS04
-#heat

9ogH 9

(b)
Ho3sd

d
o

(c)r"rrd (d)

so3H

L78. Which of the following procedures would be best for the preparation of phenyl benzyl ether ?

c 6HsocHzc oHs
(a) C6Hscl + C6H5CHTO(-)ir1u(*) (b) cuHro(-)Na(*) + c6HscH2cl
(c) 2C6HsCl + Na2O (d) 2C6H5MgBr + CH2O
 +;dtl*r##$l';#S:#Ii,##lrfi.*i+r+s"r$flH:;l*jtpih'4#i#fijirrt;ii*.'ifjiiir, rili;iii':jr+i+i,i;:":,*:li,i,ifijj*i-*K+}ri##.+ii$fiEiiir
i:jp"#fi#*rL,rFirrt#,#.gi,$,in*,#:,;l1i14ifr:i*ffiJfi+i;r**i,ifliil
, ,a;j+-t*,;r\r;;trr k:: "jit:;al{itr,
iltll,i: .1, .,,,;i:ilj.rj(sl.
.i.ri : ir+ .
+jHv,F:i,i:?.. ttili++iiiii.:lil;f;ffiffiffiffi
179. Which of the following procedures would be best for achieving the following reaction ?

cHs CH2-C-CH3
+ ?

(a) (i) KOH and heat (ii) CH3C : C Br

-
(b) (i) KMnOa and heat (ii) CH3C == 6(-)pur+) liii) excess H2O
(c) (i) NBS in CCIa and heat (ii) CH3C :6(-)pu(+)
(d) (i) Mg in ether (ii) CH3C : CBr (iii) excess H3POa
L80. \tVhich of the following procedures would be best for achieving the following reaction ?

cHs o'*l^rco2H
?
-+ d\As,
(a) (i) FeBr3
Brz + (ii) KtvtnOa and heat (iii) HNO3 and H2SOa
(b) (i) KMnOo and heat (ii) Br2 + FeBr, (iii) HNO3 and H2SO4
(c) (i) (ii) KMnOo and heat (iii) HNO3 and H2SOa
NBS in CCla and heat
(d) (i)
NBS in CCl4 and heat (ii) NaNO, and heat
181. Phenol reacts with acetone in the presence of conc. sulphuric acid to form a C15H16O2
product. Which of the following compounds is this product ?

cul Xo-tunt
' o-c6Hs (b)Hoffi",
o\
coHs

o"c6H5

182. Heating benzene in a large excess of B0% D2SO4 in D2O results in what product ?

(a) C6H5SO3D (b) C6H'OD (c) CoHsD (d) c6D6

1.83. A solution of cyclohexene in benzene is stirred at 0'C while concentrated sulphuric acid is
added. After washing away the acid and removing the excess benzene, what product is
isolated?
(a) cyclohexylbenzene (b) l-cyclohexylcyclohexene
(c) rrans-1,2-diphenylcyclohexane (d) 1, 1 -diphenylcyclohexane
L84. Indentify the reagents S and p in the scheme below in which R is converted to the nitrite Vvia
the benzylic halide T.

CH2 Br cH2 cN
(s) , - (p) -
(R) ,
{#Jli;ql..it.t,;llirlil',:i;1...i:+r.i1rl.r:r:i,.l,iir,,::, 1 .: ,: r:r. :r
""liri.:i11,, i, l
5lrmfttr.ljr*ri1.E. :-,.i.i.ii.::::!.r :!i :'.:'.. :': ::'
*ffi&ril++l:iii{'r'rr'' ;.r...'.' . ":''
"1,il'i.r.:..,,,.:i.

R, S and p respectively are :

s f-r

rul@-cr H-ii **< (Arcr3)

H-c-<?il HCN

o burs.
.')(o cr-c-5\
jl \< (Alcr3) HCN

o cH2Br

(.)@ cl-fiq t*rcr;, KCN

o bHrn,

ral C#
wll g,- cl GcH2Br (Atct3) KCN

o
185. Two aromatic compounds P and Q give product R.

G.n,
P+Q Reasent(s)
r@ir-
o
ReactantP, Q and reagent used in above reaction are :

P a Reagent

tulGc-cl
\--l ll
o
cl@cn, Alcl3,

@-",
&)(o I
C
-o
AlCl3

I
C1

o
^-'
(d)(()) ll ./-
cr-c{q}cus ZnCI2
\--z
186. Which of the follorving CoH o compounds has a single set of structuraffy .qr;;i;;;;;;;;
atoms ?

O Ef H-c-c-cHz-cH2--c:c-H@ trG
III III

(a) I and II (b) I and IV

(c) I and V (d) I, II and III
187. Which of the fcrllowing compounds would not be considered aromatic in its behaviour?

(r)O
188. A C8H10
b)
hydrocarbon
Eht
(c)
0 (d)

is nitrated by HNO3 and sulphuric acid. Two, and only t'wo,

CsHeNO2 isomers are obtained. Which of the following fits this evidence ?
(a) ethyl benzene (b) ortho-xylene
(c) meto-xylene (d) para-rylene
L89. Which of the following benzene ring substituents is deactivating but ortho-parq directing ?

(a) (b)
-N-O
(c) --COCH3
-ocH3
(d) NOz
-
L9O. Which of the following compounds forms ortho- benzenedicarboxylic acid when oxidized by
hot aqueous potassium permanganate ?

o)eD
(d)m
191. Which of the following organic chlorides will not give a Friedel-Craft alkylation product
when heated with benzene and AlCl3 ?
(a) (CHs )3 CCI (b) CHz : CHCHzCI
(c) CHsCH2CI (d) CHz : CHCI
192. Which of the following is aromatic ?

o o
@
@

(d)fi
(a)
",o (carbene)
(c)

(carbene)
 ; I .',

193. Which of the following substance will increase the acidity of phenol ?

(a) DiI. H2SO4 O) Dil. HCI (c) Conc. H2SO4 (d) Conc. CH3COOH
!g4. n\N/ +PhMgBr----)E+F

H
Pyrrole

Me
/
(}
N
I

H
7

The structure of products E - H, respectively are

(a) 3, 2. 6,7 (b) 4, 5,6, t
(c) 3, 4,5,2 (d) 3, 2,4,5

tr
195"

tr
(a)

(c) (d) none of these

 ffi$ ., *lg.rial
i&€}I*
o

H*
L95.
---_.s.

- of the above rearrangement reaction.

Identify the product
ooo
(a) (b) (c)

197. Product obtained in the following rransformation is :

PPA
-----_) PPA : polyphosphoric acid

(b)
d o

o
Ph

L98.
(c)

The compound X in the reaction.

(d)
oh Ph

anhydrous Alcl'
+ ICI
O "
,rrryt' o)ry
 OH
I

tss. O + 3Br2'+ + 3HBr

(a) Nucleophilic addition (b) Nucleophilic substitution

(c) Electrophilic addition (d) Electrophilic substitution
(e) Free radical substitution

9H, I
CHrBr

2oo. O+Br2'4O +HBr

(a) Nucleophilic addition (b) Nucleophilic substitution

(c) Electrophilic addition (d) Electrophilic substitution
(e) Free radical substitution
(P)

20!
Qq (a)

Identify major product of both respectively.

CH,-CI
l- L_.ct
,uQ (cy *'Q.,$.,
,\x
,.,d ff' .,0 d''
A.,r\ ,,\cl ,,\cl

2o2.6+Ph -N;cl- PH:10'11,6

N:N-Ph
 Characteristics of above reaction is :

(a) C N coupling reaction Carbocation is intermediate

-
(b) N N coupling reaction Carbocation is intermediate .

(c) C
-
N coupling reaction Carbanion is intermediate
(d) N
-
N coupling reaction Carbanion is intermediate
-
2O3. The compound formed on heating chlorobenzene with chloral in the presence of
concentrated sulphuric acid, is :
(a) Freon (b) DDT (c) Gammexene (d) Hexachloroethane
2O4. Predict the product of the following reaction.
o

'^-Acl/Alcl3
2.Zn(Hg),HCl
3. Br2, FeBr3

o o

,or*#
Br

(c)r.f
2O5. Predict the major product of the following reaction sequence.

v
A
Noz
cr2lArcr3
>a-jffil-+r c
Brz/FeBrs
r, NaOH
r6,

-&+f---,r-fti!---c

,",,d ",.d"(c)''q",.,''q,,
ffi ,,, Xfi1j1i1j':,;,,rr;,i1',..',....,.::1 i.i,.:.ri.-,.,i;ii :r,' i r...::...i,:.,:i:l,ti;,j
.,.ti:i.'l.ilii.:it.i.rl.i:ii:,lt ##
206. Give the major product of the following reaction :

NHPh cH3cr,Arcr3
>

(a)
Hsc

cHs
NHCoPh
(c) (d)
Hsc \l
ryNHCoPh
I
cHs

sn/uct r(B) NaNo2+HCl HsPoz

207. -+--(A; >(C) rfol-ffi-rtrl
Noz

Product (E) is :

co2H
,",0 (,,d,,,o6"
9ozH
forn

Br co2H
 tff-Ds

1. (b) 2. (d) B. (b) 4, (c) b. (a) 6. (b) 7. (c) 8. (b)

9. (d) 10. (d) r1. (a) t2,. (a) 13. (a) 14. (a) 15. (a) r6. (b)

17. (b) 18. (a) 19. (b) 20. (b) 21. (c) 22. (c) 23, (b) 24. (b)

25. (d) 26. (c) 27. (c) 28. (b) 29, (b) 80. (b) 31. (b) 32. (a)

33. (b) 34. (d) 35. (c) 36. (c) 3.7',, (a) 38. (c) 39. (a) 40. (b)

41. (b) 42, (c) 43. (c) *4, (b) 45. (c) 46. (b) 4'7. (b) 48. (b)

49. (b) 50. (b) 51. (b) 52. (a) 5S. (c) 54. (c) b5. (a) to. (a)

57. (d) 58. (b) 59, (b) 60; (b) 61; (c) 62,, (b) 6,3. (b) 6{n (b)

65. (a) 66. (a) 67, (c) 68; (b) 69, (a) 70, (d) 71" (b) 7',2t (a)

79. (a) 74, (c) 78. (a) 76, (d) 77, (c) 78. (b) 79, (c) 80, (b)

81. (b) 8.2. (c) 8!i. (a) 84. (c) 8Ei (d) 96. (b) 87. (d) 8S. (b)
gg. (d) 90. (d) 91. (d) 92. (d) 98; (d) ,; (b) 9Et (c) 96i (d)

97. (b) 98. (d) 99. (b) 100. o) 101. (b) 102; (c) r08. (d) to4; (a)

105, (b) 106. (d) LO7. (c) 108. (b) 109. (b) 1 10, (b) 111. (c) ttz, (b)

1t3. (c) 114, (a) 1,15. (b) 115. (b) tt7, (a) 118, (b) 119, (b) 120. (c)
1t1: (b) 1?,?., (b) 128. (c) I24; (b) 125. (b) t,2,6. (b) I.27, (c) r2s, (c)

l2g. (c) 130. (b) t3 1. (d) tr s2,. (b) t3$. (b) 134. (a) 135. (b) 135. (a)
Lg7. (b) 138. (c) tgg. (d) r40. (b) t4t, (b) iL42,. (c) 143. (a) 144. (b)
145. (b) 146, (c) I47, (a) r48. (c) I49, (c) 150. (b) 151, (d) 152. (c)
155. (c) 156; (c) 158; (b) 159. (c) '160. (c)
15$; (c) 154. (b) 1,8.7:" (c)

161. (b) t62. (c) 163. (d) 164. (d) 165; (c) 166. (c) 167. (b) 168. (d)
169. (d) 17o. (b) t7t. (b) 17?;; (a) 17. (a) 174. (b) 175. (b) 176, (d) I

177. (b) l7g. (b) 179. (c) 180. (a) 18r (b) 182. (d) r8s (a) 184; (c)
185. (c) 186. (b) L87. (b) rs8" (b) r.s9 (a) 190, (b) 1,91 (d) 19,2, (b)

193. (c) 194. (a) 195. (c) 196. (b) t97, (b) 198 (b) r99 (d) zCIO (e)

201. (c) 242. (c) 203. (b) 204. (c) 205 (a) 206. (c) 2U^7 (c)
1. Each of the six compounds shown at the bottom of the page has rwo aromatic (benzene)
rings. In each case the two rings are different and are labeled A & B. If an electrophilic
substitution, such as nitration or bromination, is carried out on each comfound,
then identify which ring (A or B) will be preferentially attacked, and indicate the orienration
of the substitution (ortho,/ meta or all sites).
Z. When given substituents on a benzene ring, as activating or de-activating and as ortho-para
or mera directing for elctrophilic aromatic substitution fill the following by appropriate (/)
right or (X) wrong.

[," -_ocH3

o
2,' il

-c-o-cH3
fi.; -o - c-
il
cH3

o
#i _CH:

tl.
-F
6.
-Ph
o
7,', il
-NH-C-CH3
o
.Si il
NH CH3
-c- -
xix#
-Br
$i6iii *CN
fiil
-CFs
o
il$l il
- c* NHe

o
ilSt It

-C*OH
il#; -- CHz
-CH
 o
il
-CH=CH-C-OH

r:illiti ilil o
ilffi il
--CH=CH-C-H

*.#,1
-S-Et
-S-Et
18t il
o

o
il
il.9 -S- Et
lt
o
88ii -N: O

8iil:r -cH2x

uffiin *CHX,

3. Devise a series of reactions to convert benzene into meta-chlorobromobenzene.

Select reagents and conditions from the following table, listing them in the order of use.

sulphuric acid {conc.)

Mg in ether CurBr, + HBr
heat

Cl2 + FeCl3 and heat (CH3CO)zO * fyridine

NaNo, + HrO(*) 0"c

HNO 3 (conc.) +
H2
H2SO4 (conc.) and heat
Pt catalyst

(a) 1 then 2 then 6 (b) 2 then B then 4 then 3 then 9

(c) 8 then 4 then 10 then 2 then 3 then 9 (d) B then 2 then 4 then 3 then 9
 C1

I
c
ta) Nl -rq
tlt cl
ctlc\* tc -
I
N
H-B/ \g-n
II (4n + 2)n electron in a single ring

,u* -rr* -
H

I
H

4nn electron in a single ring

Fe(CsHs)z

cr(CaH;,)a Effective atomic number of metali=,36

b Match the Column and Column (II).

,,
Nurrber of.ri.$ *#$ffiii;i

tlrl::.,'

ffi
.

ffiu caH]2 Zxe

ffil coHi' ffi) 6ne

f$l CrH$' $tr} 9xe

fal
.,.(dI CeH!1 tq, l0we
6. Match the column (I), column (Ir) and column (rlr). (Matrix)

(4n + 2)n electron.

n=Ql,ZB

4nru electron
Non-aromatic
n =1,23

Anti- aromatic Non-planar compound

Readily reacts with

Planar compound tri I

7. Match the column (r), column (rr) and column (rlr). (Matrix)

Readily react with j

active metal :
I

i
I

l
i

Readilyundergo I

Dmenzanon at room Anti-aromatic l

I
temperature i
i
I
l
(4n + 2)n electron :

Non-aromatic
n=Ol,Z3
i
1

(z)
| High dipote i

I
I
I
i
..t
 ; ,.!r'i.i+i
itrrtrt:

8. Among the following comPound.

(a) Number of compounds which are aromatic : P

(b) Number of compounds which are anti-aromatic : Q
(c) Number of compounds which are non-aromatic : R
(d) Number of compounds which readily : 5
Undergo dimerization at room temperature
(e) Number of compound which reacts with active metal : T

SumofP+Q+R+S+T=
g. Of the following compounds which will react with Br, at room temperature in dark.

Benzene (CoH^)

Cyclohexene (CoHro)
Cyclohexane (C.Htr)
noic Acid (C , H .CO, Fil

Phenol (C oH oOF0

Nitrobenzene (C 6H qNO r)
Hexyne (C6H1o)

,2-dichloropropane (C 3H 6Cl2)
Among the following compound.

(a) Number of compounds which are aromatic = w

(b) Number of compounds which are non-aromatic = x
(c) Number of compounds which are and-aromatic = -)r
(d) Number of compounds which readily undergo Dimerization at room temperatur€ = z
Sumofw+x+y*z=...
ffiuffiffi#ii# S#S"*.u
11 Comulete the followine table.

{a} (A)

I;rNaNO; in dilut'
Hs$O4/0- 5"C (B)
,r
2. heat ot boiling

r
-, :. ]

i,*"j gg=leondi,,,ffi*$ffi (c)

I,r,,NhoH.heated at iS30"G
(d) (D)
,
;,..:...i; 2; fiilute, If i6*',i.',,,,,.,',','

L, aqueous NaOH
(cI ' heated at 60"C (E)
.

.2. dilute HrO"

 $

9y:l is_ t!e_ energy profile diagram of nitration of benzene using mixed acid.
-
(HNO: r- H,SO. ).

C6H6 + NO2 Ph * NC)2

reaction-co-ordinate ,

A. Identify (x) in above reacrion :

Noz
u**o,

,r6 (b)6' ,.r6 (d) None

B. Identify T. S, in the above reaction.

NO" 5*No,
lo

,r6 (b)
6' ,o&* (d) None

C. Identify T. S, in the above reaction :

u*
NOr No,
t- NO.'
\.1''o"
,rr@ (b)
6. ,r@ (d) None
 ,,GOl,t O{IJIIpS $6i
18. Examine the ten structural formulas shown below and select those that satisfy each of the
following conditions. Enter one or more letters (a through j) in each answer box,.reflecting
your choice for each.

I (cHf 2

tf. fir

c. d:

ocH3
G. f.

9Hs
CH'
l"
g; O-i-",
\-r I

CH.
h.
I

c-cH3
I

cHg
"Ba
l-r
f:i: rrl;:r r :

li , :l
ti , :,:::, :

ll:,: .,. ,. .

I :,,'..,
:t
tl.
l:e
J

-i
I

Which compounds ufldergo, electrophilic nitration more rapidly than

t
I

benzene ? I
;
a,
I

B. Which compounds give rneta substitution under electrophilic bromination 1

conditions ?
1

l
iiii:]:; i;ii.li lii:i.i,,.ii,iii:*itf f ri

.il$,.ffitfiltlr.
1 r.!.iii;:.r1..r
:r::.1irlij1.,
l:-iit:{ritlt..ri
ri /rl.ri.ri:'i:I
ii':!+:l$fi..x..
i' rrli:ltjtiilriliir;:i -
!iir$L.rl.;E! r11lilr qii{iL!!!l:illl
E:i't:11 .+.r1
rirriii!1'1 iii i.4rn'.ilEr
r:+ri'],-,...rrlj.r:j:lifvr11.
lillJri!::l
rrj'i.li.1:.:
:i!ri: .:
):lrl'
."' :'.'
il:.il
g11r1.tti1r+1$ I#fia ffirrtdraffiB,
14. Nitrobenzene is a versatile compound that may be cr:nverted into a wide variety of
substituted benzenes. Five such synthesis are shown below. In each reaction box above an
arrow write letters designating the reagents and conditions, selected from the list at the
bottom of the page, that would effect the transformation. The reagents must be written in
the answer box in the correct order of their use. You may assume appropriate heating or
cooling takes place, and more than one equivalent of the reagent may be used if needed.

..\.,/cN
orNtU

*-(I-N:cHe
''p/*"
NH"a

ctyTruuz
H,Nt/
C1

H2, Ni catalyst Cl2 & FeCl

KBr & Cu"Br NaOH 1070 solution

KCN & Cur(CN)2 (CH3CO)2O, pyridine

HNOz 0"C HNO 3 /H 2SO 4

CH3I & pyridine
16. Match the column I and [I.
 Nucleophilic Aromatic substitution (SN6r) : .:

A substituted benzene derivative containlng- NOz and Cl group at p-position is subjected to

Nu-substitution.
CI

+ Noz
p-chloronitrobenzene
+ CH3ONa -t#=--
CH"OH

Noz
(p-Nitroanisole)
+ NaCl

(92o/o)

A. Match the column l and lL

-1- _?",
O--itrfr"-O
YYNOz NOz
 SNar'
(a) Fluoride O) Chloride (c) Bromide (D) Iodide
C. Which of the following is most reactive toward SNer. I

(a)

Noz Noz

C1

,.,d*,
C1
I

D. fA
\r HNo3
> (A) cH'o*u , (B) (Major)
, product (B) is :

cl ocH3 cl

ocH3
(c) to'op.",
Noz
Cl Cl CI

Noz

(1) NaOH, A
_.-.-_-.--------
6
(A) , Product (A) is :
(2) HgO-
I

OH

I
 HocH2cH2oH
NaOH,A
) tal _ffe__+(X) (CsHaFaO2)
F

o-cH-cHz o-cH2-cHo

OH H
F F
F F

G. Which is the best route for the synthesis of CH3O NO2 Strating from benzen of ?

Noz

(a) ), HNo3 ) HNo3 ) NaoCHg

='1, t
tetsr3 H2SO4 H2SO4 CH3OH

(b) , HNo3 > FeBr3 NaocHs t

,!19,
H2SO4 H2SO4 ,,", , CH3OH

(c) -T!o_. , ='1, , HNo3 ) NaocHg t

H2SO4 FeBr3 H2SO4 CH3OH

(d) _!19.
H2SO4
, _ul,
FeBr3
, NaocHs r HNo3 >
cH3oH H2so4

L8. Identifir product (A) and write its structure.

Ph
t--*
I

Ph
- CH
I|
t-.
--+----+
Alcl.
'-"^3
(A)
Ph

-@.,l-4.+q,'.*4-,,@,q,-,.,.-
ffiffiffiffiffffrffS;i,€#.P,S r[ffi#
SUBJEGTIVE PROBLEIIS

1.

OH
(mild - basic
ition)

6*.,#*"
(1) SnIHCI
Y, rD
fl,, rrtGoztil' +C

volatile

Double bond equivaient of D is :

2. How many isomers 'x' of CsHro when reacts with hot alkaline KMnOo give only aromatic
dicarboxylic acid ? How many isomers ]r'ofCoHs when reacts with hot alkaline KMnOo give
carbondioxide ?
Sum of x+y:z
3. How many groups are of p director in the electrophilic aromatic substitution ?

(i) (ii) (iir) O (rv)

-NHz -coH o -N: -COOH
o
il il
(v) C- (vii) (viii)
-C- NH-
(vi) Me Me
(ix) -OMe
: NHz (x) -O -g H -Et
-N -SO
2.

1.
-ocH3 / x / x
o
2i il x / x ,/
-c-o-cH3
o
3. it / x / x
cH3
-o -c-
4.
-CH, / x / x
a.
-F x / ,/ x
6,
-ph ,/ x ,/ x
o
7. ti ,/ x / x
-NH-C-CH3
o
8. It
*c-- x ,/ x /
NH CH3
-
9,
-Br x / / x
lo. x / x /
-CN
 ffilr _CF, x / x /
o
12. il x / x /
-c- NHz
o
1S.
II
il x / x /
-C_OH
14. -cH - cHz / x / x
o
*$; ll x / / x
-CH:CH-C-OH
o
f6. li x / / x
-CH:CH-C-H
t7. -S*Et / x / x
-S- Et
L8. il x ,/ / x
o
o
il
19. -S--Et x / x /
il
o
2.o. -N: O x / / x
ti[i.I; *cH2x x / x /
22; -cHx2 x / x /
3.d
4. &-p, q; b-p, ei c-p, e,S; d-p, q, s
5. u-q; b-pt c-r; d-s
6. fl -p, s -w; b -p, s --w; c- q -x,y,z; d- q-w- y
7. u-p,9, s-x; b-p-s -y;c-r-w,zi d-r -w,z
8. P+Q+R+S+I:19
9. b,e,g
10. w+x+y+z:14
#r$
*ffiffi
q
OH OH
Noz
L1. A - C12/hv

12. A-a;B-b;C-c
or SO2C12/hv; B -

Noz so3H
d CI
;E-

Noz

13. A- a, b, e, f, h; B - C, d, 8, i (lJote : yet CuHrBr is less reactive thanCuHu but of p directing)

1,4. v-F, A, D, B; w-A, H, I, G, D, C; x-A, E, D; y-F, I, AorI, F, A;
Z_ A,H, I, F, G, A oT A, H, I, F, A, G
15. &-p,si b-p,r; c-p,ri d-p,t
L6. ?-p,ri b-p,r; c-p,ri d-p,t
17. A-u-p, b-q, C-r, d- s;B-d; C-d; D-a; E-b; F-c; G-a

o
1_8.

o o
Subjective Problems
1.9 2. 5 3.6
 W"w,

Hffi ffIiEffiU ffi' HE

-zo\ oo
r.. I I and (. tcomPounds (X) and (I) can be differentiated by :

\o/ )
(a "
(n
(a) HrO@, NaOI (b) H=Ou, then Fehling test
(c) HrO*, then Na (d) Both (b) and (c)

z. Compound CH3 CH{:' and CH3 - CH, - o - CHz - CH, can be differentiated by :
- (a)
(P) (Acetariont
(a) Hro@, Na O) H3o@, Tollens'test
(c) Hro*, Fehling test (d) A11 of these
NH" NH,
l'to
3. and can be differentiated by :

O O
(aniline) (cyclohexYl amine)
(a) Hinsberg test (b) Iso-cyanide test
(c) NaNO2, HCl, then ftNaphthol (d) NaOH
 OH

4.
Q
(p-ethyl phenol)
d
anisole) (p-ethyl benzyl alcohol)
(p-methyl

Above compounds can be differentiated by using the reagent:

(a) NaOH, Tollen's reagent, FeCl, (b) CrOr, Tollen's reagent, FeCl,
(c) Tollen's reagent, CrO=, FeCl, (d) Na, Tollen's reagent, FeCl3
oo
illl
OH OH o-c-cHs
co2H
s'
d'o"
Salicyclic
d'o2Er
Ethyl
salirylate
dtj't?
Ethyl
acetyl
aceryl
salicyclic acid
acid
Above compounds can be differentiated by the salicylate. Which of the following chemical
test? (used in decreasing order)
(a) NaOH, FeCI3, NaHCO3 (b) aq. NaHCOr, FeCl3, NaOH
(c) NaOI, NaOH, NaHCO, (d) NaOH, Nzt, NaHCO,
OH

6.
d,-",
(m-nitrophenol)
Noz d.,*", d.,,",
acid) (m-nitro aniline) (m-dinitro benzene)
(m-nitro benzoic
Above compounds can be differentiated by which of the following chemical test ? (used in
decreasing order)
(a) NaOH, NaHCO3, HCI (b) HCl, NaOH, NaHCO3
(c) NaHCOr, NaOH, HCI (d) NaOH, HCl, NaHCO,

Product (A) in the above reaction is :

CH"
9r, ?" I,

,", *,
OcH-cH3 OcH2-cH3
OH 9H, ?
I

(e) Ph cH2 (d)

- -cH -cH: OC_CH3
 .6ft 'CIIEI*fi9I7f'Y
e)
itn"cl- NO,
t'
B.
O
(P)
and

(0)
d''
Above compounds (P) & (O can be differentiated by i
(a) amm. AgNO, (b) NaOH
(c) FeCl3 (d) Both (a) & (b)
9. Which of following acid give positive Tollen's reagent test.
,., CO2H ,.' CO2H CO2H
(a) (cHz)ri G) cura ,., (d) HCO2H
co2r{ co2H Jorn
LO. Which of following compounds give positive Tollen's test?

,",(IocH3 *,C)-ocH3 o.,1jIo' (OqH

Ll. Give a simple rest to differentiate cyclohexane and cyclohexene
(a) Br, lHrO (b) Bayer's reagent
(c) Tollen's reagent (d) Both (a) and (b)
12. Give test to differentiate (Bromobenzene) Ph - Br and benzyl bromide (PhCHrBr).
(a) (i) aq. KOH (ii) Na (b) AgNo,
(c) KMnOo (d) All these
18. Give test to differetiate 1,1-dichloroethane and 1, 2-dichloroethane :
(a) 2,4 -DNP then aq. KOH (b) aq. KOH then 2, 4-DNP
(c) NaHSO, (d) Lucas reagent
].4. Test to differentiate between (CHTOH) and (Ph - OH) islare :
(methanol) (Phenol)

(a) Litmus test (b) FeCl,

(c) BrrfHrO (d) All of these
15. Acetaldehyde and benzaldehyde can be differentiated by :
(a) Fehling test (b) Iodoform test
(c) Tollen's reagent (d) both (a) and (b)
L6. Ethylamine and diethylamine cannot be differentiated by :
(a) Hinsberg test (b) carbylamine test
(c) Iodoform test (d) both (a) and (b)
lZ. Lassaigne's test for the detection of nitrogen will fail in the case of :
(a) NHTCONH2 (b) NH2CONHNH2. HCI
(c) NH2NH2. HCI (d) C6H5NHNH2. 2HCl
 ,',,,:1,:1.,,,,:, .fi# #'#e Wfor IIT-Jdfr,
L8. Sodium nitroprusside when added ro an alkaline solution of sulphicle ions produces a
colouration which is :
(a) red (b) blue
(c) brorvn (d) purple
19. In Kjeldahl's method, nitrogen presenr is estimated as :
(a) Nz (b) NH3
(c) No, (d) none of these
20. In Kjeldahl's method of estimation of nitrogen, KrSOo acts as :
(a) an oxidising agenr (b) catalytic agent
(c) hydrolysing agent (d) boiling point elevator
21. The prussian blue colour obtained during the test of nitrogen by Lassaigne's test is due to the
formation of :

(a) Fe [Fe (CN) u ] , (b) Na s [Fe (CN) o ]

(c) Fe(CN), (d) Nao [Fe(CN) s NOS]
22. A compound which does not give a positive test in Lassaigne's test for nitrogen is:
(a) urea (b) hydrazine (c) azobenzene (d) phenyl hydrazine
23. p-nitrophenol and o-nitrophenol are separated by :
(a) distillation (b) steam distillation
(c) crystallizarion (d) fractional crystallization
24. rvVhich of the following reagent is used for the separation of acetaldehyde from
acetophenone ?
(a) NHrOH (b) NaOI
(c) Tollen's reagent (d) c6H5NHNH2
25. The formula of gas is [CO],. If its vapour density is 70, the value of x will be :

(a) 2.s (b) s.o

(c) s.0 (d) 6.0
26. The structure of the monomer that would give the following polymer by an addition
mechanism is :

CO2Me

CO2Me C02Me

@) Nco2Me b) z?co2Me
rcl (d) co2Me
,A-co2Me \
 .fiiil[ffi
P fe ffir"1+u1511*

27. Identify the correct set of stereochemical relationships amongst the ,'"following
monosaccharides I - IV

(D (II)

(ID

OH
(a) I and II are anomers III and IV are ePimers
(b) I and II are ePimers III and [V are anomers
(c) I and III are anomers I and II are ePimers
(d) I and III are ePimers II and IV are anomers

b. 6. (c) 7. (a) 8. (d)

11. lfall2. lfai 3. (c) 4. (b) (b)

is. lrol lro. l1.l 11. (d) 1..2. (d) L3. (b) ,.4. (d) 15. (d) 1_5. (c)

ffi Lg. (b) 20. (d) 21. (d) 22. (b) 23. (a) 24. (c)

ffi 27. (c) t t__ ----***^.^",i

 Given are the isomers of C *H *O ,.
o

6+
il
C-O-Et CHO CO"H QHz - CHO
lo

ocH3
Q cHs O-CH: CHz
(a) (b) (c) (d)

Which isomer gives positive iodoform test ?

(a) a (b) b
(c) d (d) e
B. Which isomer gives *ive Tollen's test, also reacts with FeClr?
(a) b (b) f
(c) . ,0, O
c. Which isomer reacts with NaHCO, ?
(a) c (b) d
(c) e (d) f
D. \,Vhich isomer on hydrolysis gives 1, 4-di hydroxybenzene ?
(a) a (b) d
(c) e (d) f
o
ll,*
2. ph-C-ou NaHCor
r(A)gas;ph-or{ Nu >(B)gas

Sum of molecular mass of gas (A+B:?;

L. A-d; B-b; C-a; D-b

2. 4g
 Btffii

L. Which statement correctly completes the statement ?

Except for glycine, which is achiral, all the amino acids present in proteins ......
(a) are chiral, but racemic
(b) have the L configuration at their cr carbon
(c) have the R configuration at their cr carbon
(d) have the S configuration at their cr carbon
2. Assume that a particular amino acid has an isoelectric point of 6.0. In a solution at pH 1.0,
which of the following species will predominate ?
R R
*l I

(a) H.NCHCO2H (b) H2NCHCO ?H

R R
*I I

(c) H,NCHCO; (d) H2NCHCO'

3. ThepKo valuestorthethreeionizablegroupsX,Yand Zof glutamicacid are4.3,9.7 and2.2
respectively
HO2C CHz CO2 H
xlz - --CH -
+NFI,
The isoelectric point for the amino acid is :

(a) z.oo (b) 3.2s (c) 4.9s (d) s.9s

 R

4.
I
An amino acid rnay be represented by general formula FI2N -CH-COOH. If R = -CHzCoH,
then it is phen3,lalanine (Phe) and if R =CH: then it is alanine (Ala). Find the sequence of
reagents:11T those given beiow to synrhesize phe- Ala.

(1)
i
ZNHCr{CO2H (2)
f''
H2NCHCO2CH2C6H5
cH,c6Hs cH2c6Hq
li
(3) ZNI{CHCO2H (4) UTwCHCO2CHTCoHs
(a)1and2 (b)tand4 (c)2and3 (d)gand4
5. Iso-electric point of alanine is (pH : 6). At which pH, maximum concenrration of zwitter ion
of aianine will be presenr '/
(a)pF{>6 (b)pH<6 (c)pH:6 (cl)pH:7
o
li
6. NH,-lLZ
- CLi - C_ Nri _ CH" ._ CCI.rl

ci-i:
Identify' the arnino acici obtained by hydroiysis of the above compound:
(a) Glycine (b) Alanine (c) Both (a) anci (b) (d) None of these
7, At iso-electric point :
(a) conc. of cation is equal to conc of anion
(b) Net charge is zero.
(c) Maximuin conc. of di-polar ion (Zwitter ion) will be present
(d) Al1 of the above
8. which of following aniino acid has lowesr iso-electric point ?
(a) Glycine (b) Alanine (c) Aspartic acid (d) Lysine
9. Find iso-electric point c,f given amino acid
CH, -'CH--CO2H pKr:2.2
i

NH,,
oi)
pK6 : 4.4
(a) s.a G) s.9 (c) 9"6 (d) 11.8
10. Find iso-eiectric point of the girren amino acid
o
tl
H-O- C-CH, * CH, * CH-CO2H (pKo : 2)

NH,
tt?;?, irl

(a) s.5 '0".,,.i" (d) .5

BTOMOLECTilES $,8,7
(1) )'iH" ' HC'r-
HsSO.
L1. H-C:C- H---:j:::---r(A)--
H SO. (2) - --+(B); Producr (B) of givenreactionis:
H3O3

(a) Gll,cine (b) Alanine

(c) valine (d) Leucine
12. Which amino acid does not contain chiral centre ?

(a) Vaiine (b) Leucine (c) Glycine (d) Iso-leucine

13. Which of the following is Sanger reagent ?
(a) 2,4-Di-nitro flurobenzene (b) Phenyl isocyanate
(c) 2,4-Dr-nitro chlorobenzene (d) 2, 4-Di-nitro iodobenzene
14. A D-carbohydrate is :
(a) Always dextrorotatory
(b) Always laevorotatory
(c) Always the mirror of the corresponding L-carbohydrate
(d) None of these
L5. Which L-sugar on oxidation gives an optically active dibasic acid (2 COOH groups) ?

CHO CHO CHO CHO

n--]-oH H-f ou H{oH Ho
(r)HofH (b)Ho-fu (c)HfoH (d) H
Ho --l-H H
-l-oH H
toH Ho
cH2oH cH2oH cH2oH
cH2oH
CH: N-NH-Ph
I

- N-NH-Ph
C
16. Ho rhe
, rlf; given u\- obtained
\-qrr be
\-rDctz\.rlL\. can
5,rv\-rr osazone bv
-]-H
H*-OH
|
vl/L€flllLLl L- :

I
FI oH
-t-cH2oH
(a) D-glucose (b) D-mannose (c) D-Idose (d) Both (a) & (b)
17. Which of the following pair gives same phenyl osazone ?

(a) D-Glucose and D-Allose (b) D-Glucose and D-Alfrose

(c) D-Glucose and D-Mannose (d) D-Glucose and D-Talose
18. Which of the following is the Fischer projection of L-threonine (also known as (2S, 3R)-
2-amino-3-hydroxybutanoic acid) ?

QozH QOzH CO2H 9OzH

Hc+I
r,,il*r*, (b)
"il+5,,
I
rHtil"'
l-H
(d)
t,
(c) (d) Ho

cHg cHs cHs cHs

19. Atrttlrrg dre three conlpounds shown below, two yield the same product on reaction with
warm HNO3. The exception is :
CHO CHO CHO
no -J- n Ho
-J-
--[--
n so --J-- H
(a) H -{- oH 11,) Ho n (c) uo
-f H (d) None of these
H _tOH
I
H -*- ou HA-oH
cH2oH cHs cH2oH
2A. The opticai rotation of the o- form of a pyranose is + l5O.7o,that of the form is * 52.80. In
ft
solution an equilibrium mixture of these anomers has an optical rotation of + 80.2". The
percenrage of the cr-form in equilibrium mixture is :
(a) 2\o/o (b) 3zoto (c) 680/o (d) 72o/o
21. Which of the following represents the anomer of the compound shown ?
HOCH2
-O_ H

(b)

HO OH

(c) (d) None of these

HOCH2\

HH
22. Which set of terms correctly identifies the carbohydrate shown ?

(1) Pentose (2) Pentulose (3) Hexulose (4) Hexose

(5) Aldose (6) Ketose (7) Pyranose (B) Furanose
(a) 2, 6, 8 (b) 2,6,7
(c) 1, 5, B (d) A set of terms other than these
23. For the complex conversion of D-glucose into the corresponding osazone, the minimum
number of equivalents of phenyl hydrazine required is :

(a), two (b) three (c) four (d) five

24. Which one of the following compounds will form an osazone derivative ?
(a) CHTCH2COCH2OH (b) CH3COCH2CH2OH
(c) CHTCH2CHOHCH2OH (d) CH3CH2COCH2OCH3
 sag
25.. Which of the following sffucrure is L-arabinose?
CHO
CHO CHO CHO HO -I-u
Ho J-H Ho
(b) n -l--
H u J-oH
H
HO J-n
J--o.r
I I
(a) H +oH -f on (c) Ho -f (d) H
n --l-oH Hof H uo-f_ r-r H
-fcI{,,oHou
cH2oH cH2oH cH2oIl
26. Which one of the statements concerning the equilibrium shown is true ?

Hoc.H2 T HocJ-r2 T
HO ....---s HO
OH

(a) The two structures are enantiomers of each other. They have equal but opposite optical
rotations and recemize slowly -at room temperature
(b) The two structures are enantiomers of each other. They racemize roo rapidly at room
temperature for their optical rotations to be measured
(c) The two structures are diastereomers of each other. Their interconversion is called
mutarotation
(d) The rwo structures are diastereomers of each other. Their interconversion does not
require breaking and making bonds, only a change in conformation
27. The configurations of the chiraliry centres in D-threose (sho'w,n) are :

CHO
HO H

H OH
cH2oH
(a) 2R, 3R (b) 2R, 35 (c) 25, 3R (d) 25, 35
28. Rapid interconversion of cr-D-glucose and B-D-glucose in solution is known as :

(a) racemization (b) asymmetric induction

(c) fluxional isomerization (d) mutarotation
29. Identify the correct set of stereochemical relationships amongst the ,ollowing
monosaccharides I-IV.

OH

(a) I and II are anomers ; III and IV are epimers

(b) I and III are epimers ; II and IV are anomers
(c) I and II are epimers ; III and [V are anomers
(d) I and III are anomers ; I and II are epimers
 fifi$ffffi 6fte fair'IITiEE
30. What is the structure of L-glucose ?
CHO CHO
-+oH
I

HO H H OH H

(a) H OH H?, H HO l- 'l

HO H
.,) OH
(c) I
H +oH -
(d) None of these
HO H H OH HO -#H I

cH2oH cFI2 - OH cH2 - oH

3L. What is the structure of L-glyceraldehyde?
H_C: o H
I
(a) Ho - CHz OH (b) HO + CH2OH
I

H CH=O
cH, - oH
(cJ Ho
l- (d) Both (a) and (b)
-FH I

H-C: O

rIC _ OH
il
C_OH
32. HO H , the given is enol form of :

H OH
H OH
cH2oH
(a) D-glucose (h) D-mannose (c) D-fructose (d) All of these
33. D-glucose =Ho-- A + B; A and B are :

(a) D-mannose & D-mannitol (b) D-mannose & D-Fructose

(c) D-Allose & D-Altrose (d) D-Glucose & D-Idose
34. Stereoisomers of aldoheptose is (a) and stereoisomers of ketoheptose is (b).
Ratio of a/b is :
A
(r) 1
2
o)? 1
(c) -
1
(d) 1
4

Bs. D-Glucos.
+(A); Product (A) is :

(a) D-Gluconic acid (b) D-Glucitol (c) D-Fructose (d) D-Glucaric acid
36. D-glucose & D-fructose can be differentiated by :

(a) Fehling solution (b) Tollens reagent

(c) Benedict test (d) Br, lHro
37. D-Glucose exist in x different forms. The value of x (stereoisomer) is :
(a) 2 (b) 3
(c) 4 (d) s
#$(}. :., 8g,il

....L Ho--
88. D-Mannor. D-Glucose @) ;

Product (A) oi above reaction is :

(a) D-glucose (b) D-fructose

(c) D-talose (d) D-idose
*
39. Which of the molecules below will react with Ag ?

(i) Ho
HO

OH

(i i) NTICH2CH2
HO

oH oH_
loH-_
I
,,,,,Ho#rJ--L
(iii)'-Ho\-- .oH
,T-Lo
ot{

,,,:W"#""
oH
HO

HO
cH2oH
HO o
(v) HO ocH2cH3
HO
OH

HO
HO QHz o
HO OCH?
HO

(vi)

(a) (i), (iii) and (v) (b) (ii) and (iv)

(c) (iv) and (vi) (d) (i), (ii), (iii) and (vi)
 i l' i:
I
: . : ii 1i , : : I i:
: , ,: : t; i :
; I i
i i:r i: ,
i : r.] i :i :
i;

Bg,n ffir.i,,
OH

*.,M"\!f,
HO

40. A.
uo\_Affi -: HC, oH

c" HC)
o

OH

Which of the compounCs (A-D) depicted above is NOT a hemiacetal linkage ?

(a) Compound A (b) Compound B
(c) Compound C (d) Compound D
(e) None of the above (they are all hemiacetals)
47. Which of the following Fischer projection formula is same as D-Glyceraldehyde ?
cH?oH CH2OH CHO CHO
(a) onfcHo rrrl s#ou (c) on+cH2oH (d) H+clr2or{
H CHO H I_IO
42. What is the structure of the monomer from which the following polymer was made ?

Ph Ph Ph Ph

(a) PhA (b) Ph

(r) Ph-\ rPh (d) Ph\zv/Ph
\.J
 The following structure represents a subunit of a h-vdrocarbon polymer that may be prepared
by a radical polymerization method. Identify the monomer that has been poli,rnerized to
make this polymer chain.

Choose the answer that has correctly identified the number of acetals and hemiacetals in
isomaltose.
H
/
or

,"-,-41 .,01
"o"""R
_.F(,
Ho -ou o--{)*o,
/
isomaltose HO
Acetal Hemiacetal
(a) o 0
(b) 1 0
(c) o 1
(d) 1 1

45. Predict the product of the following reaction.

HO
OH MeOH. H'
HO OH

HO^
''?-o4oue HO-
\-7--ozT-o,
@
rojL42o;"'"
HO
(o)
,o / f" J
HO
or[.'

HO- HO

(c)
)-7-o^on (d) OH

"oJ-iLo;"
MeO
MeO OH
 Which reagent/s can be used to distinguish glucose and fructose ?
(I) Bromine water (II) Tollen's reagent (ID Schiffs reagent
(a) (I), 0I) and (III) (b) (II) and (IID (c) only (I) (d) only (III)
47. Choose the peptide that matches the abbreviation Phe-Val-Ala.
ooo ooo
lln llH
HrN-CHC-N-CHC-N-CHC-OH
Il llH lln ll
H2N-CHC-N-CHC-N-CHC-OH
"lll-al ll
cHz CHCH" CHs cHz CHCH3
l' | "
cHs ir,
(a) cHg
(b)
O O
ooo ooo
llH lln ll
H, N-CH C-N-CHC-N-CHC-OH
lln llH ll
"ltl H2N-cHC-N-c
[r.-*-cTC-oH
CH, CH"
" CHCH"J cHs CHCH3
1- I
(c) cHs cHs

o (d)

1. (b) 2: (a) $. (b) 4. (c) il. (c) 6. (c) 7. (d) 8. (c)

9." (b) 10. (c) 11. (b) !2. (c) lB. (a) 14. (d) r5. (a) r.6. (d)
t7', (c) r8. (b) 19. (b) 20. (a) 21. (b) 22. (a) 23. (b) 24. (a)
25i, (c) 26. (c) 27. (c) 28. (d) 29. (d) $o; (a) 3L. (d) 32. (d)
33. (b) 34. (a) 35. (d) 96. (d) g7, (b) 38. (b) 39. (c) 40. (e)

41. (c) 42;. (b) 49. (c) 44.. (d) 45. (a) 46. (c) 47. (a)
L. Match the Column (I) and Column (II). (Matrix)
 E

One cyclic acetal form of D-galactose is shown above.

A. Which atom is the anomeric carbon ?

(a) Atom A (b) Atom B (c) Atom C (d) Atom D
(e) Atom E (0 Atom F
B. which name mosr completely describes this cyclic acetal form ?
(a) cr,-D-Galactofuranose (b) B -P- Galactofuranose
(c) cr-D- Galactopyranose (d) B -D- Galactopyranose
3. How many compound which is given below is isomer of D-Glucose ?
D-Mannose, D-Fructose, D-Gulose, D-ldose, D-Galactose, D-Arabinose, D-Ribose.
4. How many acidic group is present in given amino acid ?

@
NH3-CH-CH2-CH2-CO2H
CO'

1. d-p, r; b - e, Si c- e, si d * p,.
2. A-f;B-c
3.5
4.2,
 Ci Br
1.
A-\at-oH
I

Total number of substituent present in the above compound :

(a) 1 (b) 2
(c) 3 (d) 4
2' IUPAC name will be :
ZV-ZCH
(a) Hex-S-en-1-yne (b) Hex-1-en-S-yne
(c) Hex-6-en-1-yne (d) Hex-1-en-6-yne
CH, CH,
B. ruPAC name of XfbE'i,
(,
(a) 1 -Ethoxy- 2, Z-dimethylcyclohexane (b) 2-ethoxy-1, 1-dimethyl cyclohexane
(c) 1, 1-Dimethyl-2-ethoxycyclohexane (d) 2-methyl-1, 1-ethoxy cyclohexane
4. How many secondary carbon and hydrogen atoms are present in the molecule given below
respectively ?

Br

\
Br
(a) 2,3 (b) 2,2 (c) 3, 3 (d) 2, 0
5. Which IUPAC name is correct for the given compound ?

oHC
\<--<cHg

cHs
(a) 3, 7-dimethylocta-2, 6-dienal (b) 2, 6-dimethyloct-2, 6-dienal-B
(c) 7-formyl-2, 6-dimethylhept-2, 6-diene (d) 7-aldo-2,6-dimethylhept-2, 6-diene
6. Write the IUPAC name of the following compound :

co-o-czHs
CO-CI
(a) ethyl-2- (chlorocarbonyl) benzoate (b) ethyl-2-(chlorocarbonyl) hexanoare
(c) 2-(thoxycarbonyl) benzoyl chloride (d) None of these
t')a
7. The IUpAC name of the compound aat'zcHg is :
-
(a) rrons-2-chloro-3-iodo-2-r.r,.n.n"- rul-1,:-z-.rrro--s iodo-2-pentene
(c) rrans-3-iodo-4-chloro-3-pentene (d) cu-3-iodo-4-chloro-3-penrene
8. The IUPAC name of the compound is :
CONH"
| 'cHo
/\/v
(a) 2-methyl-6-oxohex-3-enamide (b) 6-keto-2-methyl hexanamide
(c) 2-carbamoylhexanal (d) 2-carbamoylhex-3-enal
F

9. ls:

Br
(a) 1-Bromo-2-chloro-3-fluoro-6-iodo benzene
(b), 2-Bromo-1-chloro-5-fluoro-3-iodo benzene
(c). 4-Bromo-2-chloro-5-iodo-1-fluoro benzene
(d) 2-Bromo-3-chloro-1-iodo-5-fluoro benzene
 j;r :iii ..rit:.ii;iii;.i

ffiffl
_, : 1 .:r:auilt:ill

i:,

o
il
10. The IUPAC name of CH3-CH2-fH- C- ocH, is:
czHs

(a) Methyl 2-ethylbutanoate (b) 1 -methoxy-2-ethylbutanone

(c) 3-Methoxycarbonylpentane (d) 1-methoxy-2-ethylbutanal
o
il
L 1. The IUPAC name of CH3 CH : CH C OH is:
- - -
(a) But-1-en-4-oic acid (b) 1-hydroxybut-2-en-1-one
(c) But-2-en-1-oic acid (d) But-2-en-4-oic acid

?",
12. The IUPAC name of CHr-CH- t-CH, ist
(a) 1-Methoxy-1-methylpropene (b) 2-Methoxybut-2-ene
(c) dimethylpropeneether (d) none of these
MeO
t 3. The IUPAC name of CH2:[-8-oC2H5 is:
(a) Ethyl 2-methylprop-2-enoate (b) Ethyl 2-methylprop-1-enoate
(c) 1 -Ethoxy-2-methylprop-2-enone (d) t -Etnoxy-2-methylprop-2-enal
CHE CH,

14. The IUPAC name of CH3 CH

tt CH is:
- - -CH2NH2
(a) 2, 3-Dimethylbutan-4-amine (b) 2, 4-Dimethylbutan- 1 -amine
(c) 2,4-Dimethylbutan-4-amine (d) 2, 3-Dimethylbutan- 1 -amine
o
il
15. The IUPAC name of CH3
- C- fH - lH - cH3 ls:
czHs cHs
(a) 3-(Methylethyl) pentan-2-one (b) 3- (Methylethyl) pentan-4-one
(c) 3-Ethyl-4-methylpentan-2-one (d) S -Ethyl-2 -methylpentan-4-one
o
16. The IUPAC name of CH,-CH-CH2-[-3, ir,
l'
cHs
(a) 2-Methylbutanoyl bromide (b) Z-lvtethylbutan -4-oyl bromide
(c) 1-Bromo-3-Methylbutanone (d) 3-Ivtethylbutanoyl bromide
17. The IUPAC name of CH, CH CHz ._ OH is:
- I
-
coHs
(a) 2-Phenylpropan-1-ol (b) 2-Phenylpropan-3-ol
(c) 1-(2-Hydroxy-1-methylethyl) benzene (d) 1-( (Hydroxymethyl) ethyl) benzene
CH:
I

18. The IUPAC name of CH,

- Clit- CH is:
-CH-CHz -CH3
cHs cHs I
(a) 3-Iodo-4,5,5-trimethylhexane (b) 4-Iodo-1, 1, 3-trimethylhexane
(c) 4-Iodo-2, 2-dimethylheptane (d) 4-Iodo-2, 2, 3 -trimethylhexane
CH"

L9. The IUPAC name of CH3 CH

l"
C CH" is:
-CHz --CH- - l"-
CI CH: OH

(a) 4-Chloro-2.3-dimethylhexane-2-ol (b) 4- Chloro- 2-hy dr oxy-2, 3 -dimethylhexane

(c) 4-Chioro- l, \. 2-trimethylpentan-2-ol (d) 3 -Chloro-2, 3 -dimethylhexan e-2-ol
CH:

2U-. rhe IUPAC name

"r@J"-t'o,r'
(a) 2-Phenylpropan-3-al (b) Formylethylbenzene
(c) 2-Phenylpropanal (d) Ethylformylbenzene
o
21. The IUPAC name of cHe-l-an(t"' ,r'
CH:
(a) 2-Methylbutan-3-one (b) 3-Methylbutan -2-al
(c) 2-Methylbutan-3-al (d) 3-Naethylbutan-2-one

zz. The IUPAC name of cH3-co)o ist

cH3-cH r-co'
(a) Ethanoic propanoic anhydride (b) Propanoic ethanoic anhydride
(c) 1-Ethanoyloxypropanone (d) 3 -Ethanoyloxypropan-3 -one
2i3. The IUPAC name of CH3 Cf{ CH ._ CHz OH is:
- I
- I
-
OH crHt
(a) 3-Ethylbutane-2, 4-diol (b) 2-Ethylbutane-1, 3-diol
(c) 3'-Ethylbutane-1, 3-diol (d) 2-Ethyl-1-methylpropane-1, 3-diol
24. The IUPAC name of CH3 C- C- CHq is:
'
- lt il
OO
(a) Butane-2, 3-dial (b) Butane-1, 3-dione
(c) Butane-2, 3-dione (d) 1, 2-dimethylethanedione
25. The IUPAC name of CH2 : CH-CH: CHz is:
(a) Butane (b) Buta-l,3-diene (c) Butane-l,3-diene (d) none of these

r' -CHz-"
26. The IUPAC name of CH, CH2 is:

COOH
rz
COOH
(a) Pentane-1, S-dioic acid (b) Pentane-1, S-dicarboxylic acid
(c) Propane-1, 3-dioic acid (d) none of these
27. The IUPAC name of CH" CH : CH CHO is:
l^ - -
CHO
(a) propene-1, 3-dial (b) Propene-1, 3-dicarbaldehyde
(c) Pent-3-ene-1, S-dial (d) Pent-2-ene-1, S-dial
28. The IUPAC name of CH, CN is:
I
-
cH2-cN
(a) Butane-l, 4-dicarbonitrile (b) Ethane-1, 2-dicarbonitrile
(c) Ethane-1, 2-dinitrile (d) Butane-1, 4-dinitrile
29. The IUPAC name of
' -CHr
CH2- CH-CHz is:
l' |
NH, CH,
l'
NHZ
(a) 2-Methylbutane-1, 4-diamine
(b) 3-ivtethylbutane- 1, 4-diamine
(c) 3-(Aminomethyl)butanamine
(d) 2- (Aminomethyl)butan-4-amine
CH,CI

30. The IUPAC name of CH2

t'
CH CH2 is:
ll - -
CI CI

(a) Tris(chloromethyl) methane

(b) 1, 3-Dichloro-2 (chloromethyl) propane
(c) 1-Chlorobis(chloromethyl) ethane
(d) none of these
 CH.

rhe IUPAC name of CH3 CH CH

t' CH3 is:
- fH - - - T -
OH CHs OH CHs

(a) 3, 5, 5-Trimethylhexane-Z, 4-diol (b) 2, 2, 4-Trimethylhexane-3, S-diol

(c) 1,2, 4,4-Tetramethylpantane-1, 3-diol (d) 2,2, 4,5-Tetramethylpantane-3, S-diol
32. The IUPAC name of HOOC CH : CH COOH is:
- -
(a) But-2-ene-1, 4-dicarboxylic acid (b) But-2-ene-l, 4-dioic acid

(c) Ethene dicarboxylic acid (d) Ethene dioic acid

OCH.

33. The IUPAC name of CH3

t'
CH _- CHO is:
-
(a) 1-Formyl-1-methoxyethane (b) 2-Methoxypropan-3-one
(c) 2-Methoqrpropanal (d) 2-Methoxypropan-3-al
CH,
--
I

34. The IUPAC name of CH2 C is:

-COOCH3
(a) Methyl-2-methylprop-1-en-3-oate (b) 2-Methoxycarbonylpropene
(c) 2-Methoxycarbonylprop-2-ene (d) Methyl-2-methylprop-2-enoate
35. The IUPAC name of CH3 CH : CH COOH is:
- -
(a) But-2-ene-1-oic acid (b) But-1-ene-1-oic acid
(c) But-2-ene-1-carboxylic acid (d) Propene-l-carboxylic acid
OH
I

The IUPAC name of CH. CH COOH is:

- -
(a) 2-Hydroxypropanoic acid (b) 1-Hydroxypropanoic acid
(c) 1-Hydroxyethane carboxylic acid (d) l-Hydroxyethanoic acid
37" The IUPAC name of HO -- CH COOH is:
I
-
HO-CH-COOH
(a) 2, 3-Dihydroxybutane-1, 4-carboxylic acid
(b) 2, 3-Dihydroxybutane-1, 4-dioic acid
(c) 1, 2-Dihydroxyethane dicarboxylic acid
(d) none of these
 38. The IUPAC name of CH,-CH-Q*COOH
rll
cH: o
is:

(a) 3-Methyl-2-oxobutanecarboxylic acid (b) 2-Methyl-3-oxobutan-4-oic acid

(c) 3-Methyl-2-oxobutanoic acid (d) 3-Methyl-1,2-dioxobutanoic acid
39. The IUPAC name of NC
-
CHz
-
CHz
-
COOH is:
(a) 3-Carbo>ry ProPanenitrile (b) 4-Cyanobutanoic acid
(c) 2-Cyanoethane Carboxylic acid (d) 3-Cyanopropanoic acid
cH2cooH
| -oH
40.. The IUPAC name ot it'
l(aOOH
cH2cooH
(a) 3-Carboxy-3 -hydroxypentanedicarboxylic acid
(b) 2-Hydroxypropane-1, 2, 3-tricarboxylic acid
(c) 2-Hydroxypropane-1, 2, 3-trioic acid
(d) 3-Hydroxypropane-1, 2, 3-tricarboxylic acid
o
ll
4L. The IUPAC name of CH3 C : CH-CHz C is:
- I
- I

cooc2Hs OH

(a) 4-ethoxycarbonylpent-3-enoic acid

(b) 4-ethanoyloxypent-3-enoic acid
(c) 3-ethoxycarbonylbut-2-enecarboxylic acid
(d) 3-ethoxycarbonylpent-3-enoic acid
42. The IUPAC name of CHe - 'llllllCH - C- Q- NH is:

CHsO O Br
(a) (N-Bromo) -2-keto-3-methylbutanamide
(b) (N-Bromo) -2-keto-4-methylbutanamide
(c) (N-Bromo)-1, 2-diketo-3-methylbutanamine carboxamide
(d) (N-Bromo) - 1 -keto-2-methylpropane
The IUPAC name of CH2 CH-CH2OHis:
h -C -
ll
I
cl cHs
(a) 4-Chloro-3-methylbut-2-en-1-ol (b) 1-Chloro-2-methylbut-2-en-4-ol
4-Chloro-1-hydroxy-3-methylbut-2-ene (d) 1-Chloro-4-hydroxy-2-methylbut-2-ene

i_
I
 o
lt
44. The IUPAC name of CH2 CH C CHz CH3 is:
tt
Br
-
CONH2
- - -

(a) 2-(Bromomethyl)-3-oxopentane carboxamide

(b) 1 -Bromo-2-carbamoylpentan-3-one
(c) 5-Bromo-4-carbamoylpentan-3-one
(d) 2-(Bromomethyl) -3-oxopenranamide
45. The IUPAC name of (CH3 )e C .CH2CH2C1 is:
(a) 2, 2-Dimethyl-4-chloro burane
(b) 1-Chloro-3, 3-dimethylbutane
(c) 4-Chloro-2, 2-dimethyl butane
(d) none of these
46. The IUPAC name of CH,
"ltl
- CH- CH- CH-CHO is:
CH, OH OH
(a) 2, 3-Dihydroxy-4-methylpentanai
(b) 1-oxo-2, 3-Dihydroxy-4-methylpentane
(c) 2,3-Dihydroxy-4-methylpentanone
(d) 1, 2-Dihydroxy-3-methylbutanecarbaldehyde

47. The IUPAC name of CH3 _- CH CHr CH2CI IS:

-CO l' -
cHs
-
(a) 1-Chloro-3-methylpenran-4-one
(b) 1-Chloro-2-(oxoethylbutane)
(c) 5-Chloro-3-methylpentan-2-one
(d) 3- (2-Chloroethyl)butan- 2-one
oHo
48. The IUPAC name of cH3
- i - cHz - !-cH3 is:
I

H
(a) 2-Hydroxypentan-4-one
(b) 4-Hydroxypentan-2-one
(c) 4-oxopentan-2*ol
(d)'' 2-oxopentan-4-ol
 ff#$
49. The IUPAC name of CH3 CH- CH- CH- CH3 is:
- lll
Cl Br OH
(a) 3-Bromo-4-chloropentan -2-ol
(b) 3-Bromo-2-chloro-4-hydroxypentane
(c) 3-Bromo-2-chloropentane-4-ol
(d) none of these
Br Cl

50. The IUPAC name of CH3

ll
C is:
-CHz- I
-CH-CHz -Cl
OH
(a) 3-Bromo-4, 5-dichloropentan-3-o1
(b) 3-Bromo- 1, 2-dichloro-3-hydroxyPentane
(c) 3-Bromo-1, 2-dichloropentan-3-ol
(d) 3-Bromo-4, 5-dichloro-3-hydroxypentane
51.. The IUPAC name of CH, ,l- CH- CHz O
- - C 2Hr is:
OH

(a) 1-EthoxyproPan-2-ol (b) 3 -Ethoxypropan-2-ol

(c) 1 -Ethoxy-2-hYdroxYProPane (d) none of these r

T',
s2. rhe IUPAC name
"tQ ,r'

Br

(a) 4-Bromo benzenamine (b) 4-Amino-1 -bromobenzene

(c) 4-Bromo benzenamide (d) 1-Bromo benzencarboxamide

\N/

53. The IUPAC name of

(a) N, N-Dimethyl aminobenzene (b) N, N-Dimethyl benzenamine

(c) (a) and (b) both are correct (d) none of these
 s4. rhe rupAC name
"rfot,r,
(a) 2, 6-Dimethylhepta-2, S-dienoic acid
(b) 3, 7-Dimethylhepta-2, S-dienoic acid
(c) l-Hydroxy-2, 6-dimethylhepta-2, S-dienone
(d) none of these
55. The IUPAC name o,
ffrr.rs:
(a) 3-Methylpent-1-en-4-al (b) 3-Methylpent-4-enal
(c) 3-Methylpent-4-carbaldehyde (d) 3-Methyl-5-oxopent-1-ene
56. rhe IUPAC name of AO tr,

(a) 2-Phenyl ethanone (b) l-Phenyl ethanone

(c) 1-(Oxoethyl)benzene (d) 1-(Ethyaloxo)-benzene

57. The IUPAC name of

(a) 2-Hydroxybenzenol (b) 1, 2-Dihydroxybenzene
(c) Benzene-l, 2-diol (d) 2-Hydroxyphenol
oHo
58. The IUPAC name of

(a) 2-Carboxyphenol (b) 2-Hydroxybenzoic acid

(c) 1 -Carboxy-2-hydroxybenzene (d) 2-Carboxy- 1 -hydroxybenzene
OH
59. rhe IUPAC name
"r1)--,r,
(a) 1,3-Dimethyl phenol (b) 1 -Hy droxy-2-6-dimethyl benzene
(c),2, 6-Dimethyl benzenol (d) 2-Hydroxy- 1 -3 -dimethylbenzene
 ' ' "" ',
:i.i;-i:,r.. .':.i'rrr...'....r.,i:r' ....:.:I' j:r '1:i],, -.1ii.,,^irrf.i,r
'1.,r11ii.,..

'
"''l:l' i: il.:. !: r /....'. ''r.i:l.ii-r : i.j:': :i iil :.+

Ilrfi4$Af+*ffi,uir1" ':,'l;"'':' ''i",.

i ..r!
i,
::
:'
"1.' 'i;'
o
il
60. Ph-CH
- CH-C-OH
The IUPAC name is :

(a) 3-phenyl prop-2-enoic acid (b) 3-phenol prop-1-enoic acid

(c) 3-carboxy-prop-1-ene benzene (d) but-2-enoic acid

6r.. The rUPAC name is:

"trCl
(a) Chloromethylbenzene (b) Chlorophenylmethane
(c) (a) and (b) both (d) none of these
62. The IUPAC name of the compound having the formula is :

CH

HsC-A-CH:CHz
t'
I

CH,

(a) 3, 3, 3-Trimethylprop-1-ene (b) 1, 1, 1-Trimethylprop-2-ene

(c) 3,3-Dimethylbut-1-ene (d) 2,2-Dimethylbut-3-ene
63. The IUPAC name of the compound CH2 : CH CH(CH, )z is
- :

(a) 1, 1-Dimethylprop-2-ene (b) 3-Methylbut-1-ene

(c) 2-Vinyl propane (d) none of these
64. The number of sigma and pi-bonds in l-butene 3-yne are :

(a) 5 sigma and 5 pi (b) Z sigma and 3 pi

(c) 8 sigma and 2 pi (d) 6 sigma and 4 pi
65. The IUPAC name of C6H5COCI is :

(a) Benzoyl Chloride (b) Benzene chloro ketone

(c) Benzene carbonyl chloride (d) Chloro phenyl ketone
66. The IUPAC name of the following compound is :

d
OH

CN
J,
(a) 4-Bromo-3-cyanophenol(b) 2-Bromo-5-hydroxybenzonitrile
(c) 2-Cyano-4-hydroxybromobenzene (d) 6-Bromo-3-hydroxybenzonitrile
$6$;rf;"ii,, ,,',,,.
.',
i,i-#;',"lrirli lilffiltfil i*ffi
67, Maly organic compounds contain more than one functional group. Which of the following is
both an aldehyde and an ether ?

\-o-5 - \_^
i
,2o
(i)
Yo,
(ii)
<X (iv)

ocH3

(a) (i) only (b) (i) and (iv)

(c) (ii) and (v) (d) (iii) and (iv)
68. What is the sum of positions assigned to bromine while numbering the Parent Chain in the
below compounds ?

n
Br Br
Brl I

\./\

-\,
(r)
)-)
(II) (rrr)
-v GV)
(a) 13 (b) 14 (c) 1s (d) 16
69. How many number of compounds, which have same IUPAC name ?

OH

,/\r ..,/oH /.'z\ I

OH
/v(oH

Xr' Lo*, ,/\.,/

I

I
,)"
OH
OH
(a) 0 (b) 1 (c) 2 (d) 3
 6,O9

70. How many total number of substituents are present in the following compound,i

(a) 3 (b) + (c) s (d) 6

71..

Correct IUPAC name :

(a) 1 -methyl-3-ethylcyclohexene (b) 5-ethyl- 1 -methylcyclohexene

(c) 2-ethyl-4-methylcyclohexene (d) 3-ethyl- 1 -methylcyclohexene

(a)

(d)
(c)

(b)

(b)

(b)

(b)

(b)

(b) loz. l(b) (c) I69. I(a) lzo. l(c) lzr. lG)
 Give the IUPAG name of the following compounds

1. : 'A,lt
tlfr z. i,. oH 3' Yo' I

1:B,F
'
,tt , ,,'

6'v u*,
CI
.:
,

,HO
7. -l
-/A\-Br
\fcr
I 8.
t'Y
(Y
CI

g' oH

HO OH
".

HO ;.
HO OH

"iliffifil 11.
o 12.
I

CI1
rB ,hon
A
t4.
# HO OH
ls.
\-
(\o,
-\

HO

t7 18
*odo* ru'
 >#
.A---rff
re.
ffi 2t. J
l

22'G rlr
,e*.*
iga
i,.,,lffi
#
..,.;i,
j...,ifr
:l ; ti .
: l;i L I
:
, l. I : ,i i I
i: : i tl I
ti ll
: t
'.

2s. t\rrSZ - 26.J'- - 27.

a'\r/
-
ilt
rF
28.1 ,

29. ./-:J/
\J 30.
I I

BB ffiHi
b
\r/V

v
I

87. ryn, 39.

\oL
o
o
42.
fo Ao
 44. \
\o

o Cl<A I ct .g
46. >-( 47. ruHf--{ 4g.
' \Pft-Br
d,. NH-Br c! J,
(7
\/
OnY Br

4e.' I \N.\
^Y

so.- .*,---tf t
"-.. T \,,rAst.
\rANH
.
\./\ l_\

C!
iBr o Yo
fi{yo
o
sz.
f'^(-fi\,,cr ss. Y( s4.

Br Cl BroBr
t'I
^fx^\
o o
ss. /\/W 56. 57.
I I er
BrC I itti--'"" BrN Br

o
o
s8.
t(1Hy-cr se. A 60. oan(o
L/A o\ \

V
o
+o
I

61'
I

62.
o^A lr
tl
/\,\
 lll lll lll lll

63.

o
ll
-NH
rO
\ff{
cl tr bH

Ol )
oYo
[,)
67' ,)
68.

o %"o\
oY"'

o
70.

?H
O=S=O

+0
N
l-
o
 r0,i*pG ',,,

7s-#"
CI
74. ,,,,.,,,75.
,:l:

,:i
ffi
'
-,Cl.
. .::!
::t.!
.',,t,,.,
:..
'

: :,,,1 t !

oron
tl:
:ir.;

.rlt.

-,
76. ,';; 78.
Q
o4o
,'

,,
'oQ o
u o*
\^
,Br'tr \)

Hr
83.

oAo
,H,'
HS

o11o
)
-L ,cl

+
(. -t)
87.
Y
So
'
8f,,, ',.,
 )
o\,

",Ao
oY-r
91.
q' Br
e2'
D
ox^X tsr oY
s6.
94.
,r4
95.
A */o
I

ct o-
,:
os/o*? O,: '

[[,.:
'' '
ff
'

Q'' ,0,.'*,CH3
97.
ry*lo_ eB.

-o-*lo

roo
i fl
a>-c-o-cH3 1o1. l-l
cH,-cHo
-..8 ro2. 9.Lco2H
V l-l

*."^)--
o
1o4.
103.
- Cl-lz - ! - Cl-t = Cl{ : C&*C$lf kco2H
l-Hl
I :.:: \-J
cHs
 ... .: fi r : ij : '

..ffi6,,''r ,r ,
tr..j
,

o
ll corrt 106. CHs NH cHo LO7.
105. - -
tlV

o CN
ill
Ltt7. ,A- 3
OH
P6 11o.
rr'
1oe.
Lr\",-rYrr- -
NH
- (,
Br

CON H2 cHo
CHO t-
tBr

a
L13.

A
112.
1L1.
tt
\-/

co2H 9ozH

tt4.
a
COrH
- 1,s.",-f"" 116.ftt
- cN Noz

117.
f
?
co2H

o
cl
1L8.

NHz
11e.
Gc:o

,
 sr7

121,.f N'
.o
I

o-

o
il

-o r24. .o rzs. O
ry
N' I

o-

&ll._o_
126. t- )
Y
127. r28. T
HzN
o -s-o
I

OH
13o. Give the IUPAC name of the following compounds :

(a) cH3 -cHe - [r-cHz -cHz -cHe -cHz -cHz -cHz -cHz -cHz - [r-ar,
oH cH*
'(b) CH3 -CH, -ffi-Ct*t,iCHr -CHr'-,'C*r'i4*pffi *anz -GH, * CH ".,GlIg
cHs

(c) cH3 cH2,* eH;-

- cHi
?", TH2 -
CHs-CHz.CH-CH-CHB
cHs cHr
CH,
-s
r-

+:x:
(e)
 1*'

(d) (e) +
+

CHr
l-
"l
l"l-
QHs CH-CH3

cH"-cH-c-cHz-cHs
I

(k) CH3-CH2-CH2+CHr;,'SH"+CH,-CH2+-CH2$H3
 r :. '' 11:1,1
;' ,,. .'
ffi ,
::""...:
, ..
:.:.
l1
1,: t. .
.

1.32. Match the Column :

ffiS ,,fi e
CI

,,4 Br
1, 3-dibromo-2-chlorocyclopropane

.,4 1, 2-dibromo-3 -chlorocyclopropene

3-bromo- 1 -chlorocyclopropene

Match the Column :

{ (rJ 1 -butyl-4-methyl cyclohexane

{b} (qI 2-bromo- 1, 1 -dichloro cyclohexane

I (i) l" -Bromo- 1, 2-dichloro cyclohexane

I
Ethyl-2-formyl cydohexane carboxylate i
1

i
r""""""."'',."."',,''"""...^"..- |

1. 4./F
When IUPAC name of following compound is given, then double bond and substituent gets
respectively
(x and y) number so the sum of (x + y) will be
rcff 681

pent-4-yn-1-ol pent-4-en-1-ol

(58) -2 -bromo-3-chlorohept-5-en- 1 -ol 3 -bromo - 2 -chloro - 6- ethenylcyclohexanol

4-bromo - 3 -chloro - 5 - cyclopropylcyclohexanol

3 -bromo - 2 -chloro - 5 - methylidenecyclohexanol

3 -bromo-2-chloro-5 -methylidenecyclohexane- 1,4-diol

2 -bromo -4- chloro - 5 -ethynylcyclohexanol cyclopenta- 1, 3 -dien- 1 -ol

2 -bromo-5-chlorocyclopenta -2,4- dien- 1 -o1

cyclopent a-2,4 - dien- 1 -ol dodec- 1 0-en-4-yne-3,8-diol

1 -chloro-3 -methylbut- 3 -en-2-ol 4-bromo-2-chlorooct-6-ene-3, 5 -diol

3-chloro-5-(1-methylethenyl)cyclopenta- 1,3-dien- 1-ol

2 -bromo-5 -chloro-3 -methylidenecyclope ntanol

cyclohexane- 1, 3, 5 -triol cyclohexane-1,3-diol

cyclopenta-1,3-diene (6E)-oct-6-en-1-yne

but-1-en-3-yne (32)-pent-3-en-1-yne

buta-1,3-dryne (2E)-dec-2-en-5-yne

(62) - dodec- 6-en-2 -yne pent-1-en-4-yne

4-ethynyl- 1 -methylcyclohexene cycloocryne

(2E) -hex- 2-en-4-yne 5 -ethynylcyclopenta- 1, 3 - diene

5- (prop-2-enyl) cyclopenta-1,3-diene

3, 5 -dibromo-2 -chloro-4-ethenylcyclohexanol

cyclopropylmethyl cyclobutanecarboxylate

cyclobutylmethyl cyclopropanecarboxylate

ethyl ethanoate 2-methylpropyl butanoate

prop-2 -enyl 3 -ethylpent-4-enoate 4-methylpentan-2-one

2, 5 -dimethylheptan-3-one octa-1,7-dien-4-one :

41. | 3,4-dimethylheptane-2,6-dione e n9 - r 5 0 -,'i:

::.lll3 ;meth/*1 ": 1": 1 :*"__ i
.ffi ffi *;1tui*rfifl ili#fffit#tffi
;rill";t rj.il,1'r.r]itiii.'r:i:1iitl: :1". lrirlriliilli.li,:.
1

48,; 5-methyloctanal *4. but-3-enal

45. 3-ethylheptanal 4}6. N, 3 -dibromobutanamide

+7. 4-chloro-N- (3 -chloroburyl) butanamide

48, 3 -bromo-N- (2-bromoethyl) -4-chloropentanamide

49. N, 3 -diethyl-N-propylpentanamide

50. 3 -cyclopropyl-N- (3 -cyclopropylbutyl) pentanamide

51. 4-bromo-N- (3 -bromo-2 -chloropropyl) -3 -chloropentanamide

52. 3 -bromo-4, 5 -dichloro-N- (2 -chloroethyl) hexanamide

5S. (5E) -N- (prop-2-en-yl) oct- 5 -enamide

54. 3 -chloro-N- (2-cyclopenrylpropyl) -4-cyclopropylpentanamide

:,D. 5, 6-dibromo-3,4-dichloro-N- (2 -chloroethyl) heptanamide

56. 3-bromo-N- (3 -bromoburyl) butanamide

5-7. 3,4-dibromo-N- (3,4-dibromoburyl) pentanamide

59. 4-bromo-N-(3-chloro-2-cyclopropylpropyl)-3-(cyclopenta-2,4-dien-yl)butanamide
59. 2-oxopropanal 60. l4-o*ooentanal
l'j
I

51. 3-oxobutanal 62. 3,4-dicyclopropyloct- 7-yn-2-one

69. (28,68) -4-bromo-5-chloro-8-cyclopropyl- 1 0-oxodeca-2,6-dienoic acid
64,
65, (X,68) -5,9-dibromo-4-cyclopropyl-6-formylun deca-2,6-dienoic acid
66. 3 -bromo- 5 -chloro-6- (formylamino) hexanoic acid

6?. ethyl 3-phenylpropanoate 6S. ethyl methyl benzene-1,3-dicarboxylate

69. ethenylbenzene 7A. benzoyl chloride
7t, me thyl 4- acetyl-2-nitrobe n zo ate 72. 2-f ormyl-4-sulphobenzoic acid
73. 1,2-dibromo-4-chlorobenzene 74. ocrylbenzene I

75. 2-bromo- 1 -chloro-4-nitrobenzene 76. 4-formyl-2-sulphobenzoic acid i

77. 3- (trichloromethyl) benzoic acid 78. 4- (ethoxycarbonyl) benzoic acid

 79" 4-ethenylbenzoic acid 8(}. 4-benzylbenzoic acid

sl. biphenyl E2. 1, 2, 5 -tribromo-3,4, 6-trichlorobenzene

83. ethyl 4-acerylbenzoate 8*; 2-bromo-6-chlorophenol

85" 2, 4, 6-tribromophenol i8fl ethyl 4-bromo-3 -chlorobenzoate

8;V,i ethyl 3-drloro4mercapto/sulpho benzoate 88. ethyl 4- (chlorocarbonyl) benzoate

89i 3 -bromo-4- sulphobenzaldehyde ffi; benzene-l, 3-dicarbaldehyde

91, 4-bromo- 2 - chlorobenzaldehyde 92. 1-phenylpentan-1-one

93. 1 - (3 -bromophenyl) hexan- 1 -one

94. 4-bromo- 1 - (3 -bromo-4-chlorophenyl) pentan- 1 -one

95. 1 - (3 -bromo- 5 -chlorophenyl) -2 -chloroethanone

96: 1- (3 -nitrophenyl) ethanone 97". 2,4-dinitrobenzoic acid

98. methylcyclohexane carboxylate 99. 2 -methylcyclopentane carboxamide

tr00. methyl-2-bromocyclohexane carboxylate 101. 2- (2-methylcyclobut- 1 -enyl) ethanal

r02 4-formyl-2-oxoryclohexane- 1 -carboxylic acid

ro$ 5 -cyclohexyl-6-hydroxy-5-methylhex-3 -en- 1 -oic acid

ro,*i 2-oxoryclohexane- 1 -carboxylic acid l05, ethyl-2-oxocyclohexane- 1 -carboxylate

r06. N-methylmethanamide 1fi7. 2 -bromo-4-chloro- 5 -ethynylcyclohexanol

,tO8r 2-bromo-6-chloro-3 -methylidene-cyclohexanol

109. N-phenylcyclohexane carboxamide :tlo, cyclohexane carbonitrile

111. ryclopentanecarb alde hyde Ita cyclohexanecarboxamid e

1.I8i 2 -bromo - 6- me thyl- cyclohexanecarbaldehyde

rt4'; cyclopropane carboxylic acid

115. 4- qno -2-hydroxy- 5 -nitro cyclohexane carboxylic acid

t'I5. 6-chloro- -cyno-4-nitroryclohex-2-ene carboxylic acid

u
5

6-chloro-4-(3-oxo cycloburyl)cyclohex-2-ene carboxylic acid

4- (2- amino-4-hydroxycyclopentyl cyclohex-2-enecarborryIic acid

irrq']
 I

r ,*
cyr c I o h e xyl ide neme tha no ne 2-bromo-4-chloro- 1 -methylb"rr.*-"'-'
L, 2 -d iethyl- 3 -methyl -4-propylbenzene 1 -ethyl-3 -nitrobenzene
2-methyl- 1, 3, 5-rrinitrobenzene 1 -methyl- 3 -nitrobenzene
Diphenylmethane 4-Methyl-3-nitrobenzene sulphonic acid
1 -e th enyl -4- me thylbenzene heptan-3-amine
2-methylpentan-3-amine
(a) 2, 1 1 -dimethyltridecane

(b) 1 2-methyl-tridecan-3-ol
(c) 4-ethyl-3 -methyloctane

{d) 7,2,7-trimethylcyclopentadecane
(e) 1, 1, 2, 5 -terrarnerhylcyclopentane
(a) 5-isobutyl-2-methylnonane, 5-2-methylnonane (2-methylpropyt)
{b) 2,7 - dimethyl -4-propyloctane
(c) 6-(2,3-dimethylburyl) 3-methyl undecane
(d) 1, 1.2.6-retramethylcyclohexane
(e) 2,2,3 -tr:imethylcyclohexanol
(n 1,2,4-trim ethylcyclopentane
(g) 2-methylbicyclo[3. 1. 1] heptane
(h) 2-methylbicyclo[3. 1. 1] heptane
(i) 2,2,6,6,7 -pt entame thyloctane

U) +- (lmethylpropyl)-2,3,5-trimethyl nonane Not 2-butyl

(k) 5-( 1 -ethirl-2-methyl-1 -(1 -merhylethyl)propyl) nonane

Subjective Problems
1.4