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Acidic and Tautomerism PDF
Acidic and Tautomerism PDF
XII (ALL)
QUESTION BANK ON
ACIDITY, BASICITY
H-BONDING
&
TA UTOMERISM
Write equations showing the Lewis acid-base reaction that takes place when
Methyl alcohol reacts with BF3.
Methyl chloride reacts with AICI3.
Dimethyl ether reacts with BF3.
Which of the following are lewis acids & which are lewis bases?
CH3
CH3
CH3
(d)
^/C?. 3
(C)(C6H5)3P:
(b) CH 3 -C
(a) CH 3 CH 2 -N-CH :
(f) m
*(e) (CH3)3B
:Brf
Which would you expect to be the stronger acid? Explain your reasoning in each instance.
CH2C1C02H or CHC^CO.H
CC13C02H or CHC12C02H
CH2FC02H or CH2FCH2C02H
'
,Jb)
Jt)
Q. 4
(a)
(b)
(c)
(d)
(e)
(f)
(g)
Write equations for the acid base reaction that would occur when each of the following compounds or
solution are mixed. In each case label the stronger acid & stronger base,& the weaker acid & weaker
base.
NaH is added to CH3OH
NaNH2is added to CH3CH2OH
Gaseous NH3 is added to ethyl lithium in hexane
NH4C1 is added to NaNH2 in liq. NH3
(CH3)3CONa is added to H 2 0
NaOH is added to (CH3)3 C-OH
C2H5OH is added to a solution of HC = C~Na+ in liquid NHV
Q.5
CHjCHjMgBr + CH3C = CH
>A+B
Choose the member of each of the following pairs of compunds that is likely to be the stronger base.
v
(a) NH 2 or NH3
( Jb)
o-
OH orH 2 0
J c ) O H or SH
Choose the member of each of the following pairs of compunds that is likely to be the weaker base.
2
H 2 0 or H30
(C) CI", SH
v , (b) H2S, HS- S ~
J d ^ F - , OH~ MTV, CH3
J e ) HF, H 2 0, NH3
[2]
Q.8
Label the reactants in these acid - base reactions as Lewis acids (electrophiles) or Lewis bases
(nucleophiles). Use curved arrows to show the movement of electron pairs in the recations.
(A)
CH 3 O:
(b)
CH3-O-CH3
+CH3-CI:
->CH, - O^ C H V + lC i r
+ :O-H>CH3 -O:
CH 3
CH 3
:o:
II
(c)
+CH^-P-H
H - C - H + :NH 3
IS
M
->H-C=RH
NH 3
(d)
CH 3 - N H 2 + CH 3 - CH 2 - C I : - > CH 3 - N H 2 - CH 2 CH 3 + : C I :
(e)
(CH3)3CC1 + A1C13
JL4
+ BR
(f)
"Or
> (CH3)3<?H^A1C14
B E> CH-J C HO
CII3 -FC*C H F ^ O - H
CH3 - c = CH 2 +H - O - H
(h)
BF3-CH2-CH2 + CH^CH,
Q. 9
Q.10
(a)
(b)
Q.ll
Q.12
B F3 CH 2 CH 2 CH 2 C H 2
CH 3 - C - CH 3 + HSO4
Which reagent in each pair listed here would be the more reactive Nu in a protic solvent ?
xJ$)
CH 3 NH- or CH3NH2
(b)
H 2 0 or H,0
CH 3 SH or CH 3 OH
CH 3 0- or CH 3 COO
^ (d)
y M
CH 3 COO" or OH
k)
Ph 3 N or Ph 3 P
NH 3 or NH4
H.S orHS"
Each ofthese molecules is electrophile. Identify the electrophilic atom & draw a mechanism for reaction
with a generalised nucleophile Nu", giving the product in each case.
(a)
(b)
(c)
(d) CI - CI
X
(e) MeO OMe
& Tautomerism
[3]
19
NH2
rol^Ta
^bf.
Jtf
CH 2 = C H - C H = C H - C H 2 " or
0
II
II
0--C-C-0H
OH
j *
Q. 20
or
CH^CH-CIV
0
II II
HO-C-C-OH
OH
( o r *
[or"
[OJ
[or
(i)
(ii)
* (iii)
NHt
NH2
for
"
LO
NO,
(iv)
L Q
CH3
(i)
(ii)
(iii)
(ii)
(iii)
(iv)
NH2
(c>
(i)
Q. 21
(a)
(b)
Dimethyl furmamide (DMF) is an example of polar aprotic solvent, aprotic meaning it has no hydrogen
atoms attached to highly electronegative atoms.
Draw what you predict to be its most important resonance forms.
DMF when used as the reaction solvent, greatly enhances the reactivity of nucleophiles. e.g.
NaCN + CH 3 CH 2 Br
> CH^CIi, C = N + NaBr
Suggest an explanation for this effects.
Q. 22
(a)
OH-
CH3COO-
ft
Or)
(ii)
CHeC"
CH 2 = CH-
(i)
(pf
^
(H)
CH2 = C H C R j N R ,
0)
Gi(iii)
CH3CIV
(iii)
CT^CI^CI^ML,
CH = C - C i ^ W ^
Oi)
d)
[5]
Q.13 Each of these molecules is nucleophile. Identify the nucleophilic atom & draw a mechanism for reaction
with a generalised electrophile E+, giving the product in each case.
WR-C.C-
OMe
I
(ONH.-NH,
NH
IT
( d ) M e O / ^OMe
(e)
^ M e
x&f"
CH 3 0- CH3NH-, CH3CH2
yjdf
Q.15 Neither of these methods of making pentan-1,4 diol will work. Explain why not-what will happen
instead?
(i)
MeM
followed by H +
OH
(ii)
Br-CH2-CH2-CH2-OH
MgBr-CT^-CH^CH^OH
OH
f
C H 3 - C H - C H 2 - C H 2 -CH 2
I
I
OH
OH
Q 16 Suggest what species would be formed by each of the following combinations:
(a) PhO - + CH3COOH
( b ) H N ^ N H + CH 3 COO(c) Pyridinium ion+trifluoroacetate ion
Q.17
(i)
Say which pka belong to which functional group in case of following amino acids:
^COOH
cysteine: HS
J
: 1.8,8.3 & 10.8
NH2
(ii)
glutamic acid : H 0 2 C \ ^ \ ^ C O O H . 2
]9>
4 25, 9.67
NH2
Q.18
Record the following sets of compounds according to increasing pKa ( = - log Ka)
OH
(a)
^b)
)JfSf
OH
[5'5]
NH 2
NH-C 6 H 5
NH 2
(ii)
(iii)
LO
(i)
NH,
NH,
V^O
fO
(i)
(ii)
ci-
0H-
RO-
NH 2 -
(iii)
(iv)
(v)
RCOO(ii)
(i)
Q.23
CI
(iii)
ff
^NH
NH
-NH2
NH
h' (iii)
J*
Q.24
(a)
=o
T-C-CH,
O f o
OH
(i)
(iii)
OH
OH
CH 3 - OH
O,
CN
(iii)
(ii)
(i)
O
CH3-C-OH
H0-C-C-0H
(ii)
0
HO-C-CH2CH2
J-
OH
(iii)
[6]
v yO .25
jffi
^Jfy
nu
9H
OH
^J y )
9H
X.
OH
ho2
o
.
CN
CN
Q-Q-J&
H
^ fafff
Ui)
CH3N02,(N02)2-CH2,(N02)3-CH
H H
CN
CHO-CHL-CHO, C H 3 - C
- C H 2 - CII- C H 3 , E t - 0 - CII - C H 2 - CII-O - E t ,
0II
0
0
0
Et - O - C - CH2 - C - CH3
II
II
Q. 26
(a)
(b)
i
Cyanic acid (HO-CsN) & isocyanic acid (H-N=C=0) differ in the positions of their electrons but their
structure do not represent resonance structures.
Explain
Loss of a proton from cyanic acid yields the same anion as that obtained by loss of a proton from
isocyanic acid. Explain.
> PhCH=CH-Br + C0 2
Q.28 Arrange the increasing order of acidic strength ofthe following compounds.
v>r ^
rb
CH,
(i)
(ii)
Col,
(iii)
CH 2 C0 2 H
(b)
[QJ
CH 2 =CH-CH 2 C0 2 H
(i)
CH3OH
(i)
()
CF3OH
(ii)
CH^CO.H
<*)
CCI3-OH
(iii)
[7]
x-(29
^ a ) CH3CH3 BrCt^NO,,
^ C O )
or
O=C~CH3
SH
Jd)(0
'
O=C-CH3
OH
CH3
Mo) <* ( O )
^jaf.5 0 Which ofthe following would you predict to be the stronger acid ?
^Jb)
^Jc)
CH3-CH2-C-OH
phenyiacetic acid,5
Ka = 5.2 x 1(T
J(s)
Jfo)
Jjz)
propionic acid,
pKa = 4.87
< ^ y ~ C H 2 C O O H + CH3CH2COO
Q. 3 3 Explain why the 2-methylpyrrolidine boils at a higher temperature than its isomers N- methylpyrrolidine.
U- UneO'l
Q. 3 4 Although nitration usually causes elevation of B .P. yet the nitration of resorcinol to 2-nitroresorcinol
decreases their B. P. then their parent compound.
5 o-nitrophenol is sparingly soluble in water & has lower B .P. but p-nitrophenol is completely soluble in
water & has high boiling point.
6 When 3 0 ml of ethanol and 5 ml of water are mixed the volume of the resulting solution is less than
35 ml. Explain.
<f| Bansal Classes
[8'5]
^ Ammonium salts are much more soluble in water than are the corresponding sodium salts. Explain?
QS 8 HF has a dipole moment of 1.82 D, its boiling point is 19.34C. Ethyl fluoride has an almost identical
diploe moment & has a larger molecular weight, yet its B.P. is -31.TC. Explain.
J&39
Give structure for ethanolamine showing two different intramolecular H-bonds & discuss their relative
strength.
f
(b)
..
N-H
(c)
( d ) ( \
H
HoXr
NC^H
HOaH
Q. 47 Trans isomer ofindigotin is stable w.r.t cis isomer. Explain.
A
Q. 4 8 What is the attacking site of conjugate base oftriketo form ofphloroglucinol in protic & aprotic solvent.
\JQC49 In each ofthe^ollowing pairs which is more stable:
H (I)
(11)
O
0 H
(I)
(nf
C 3
/OH
(J^NH
0
C
u
0 H
(11)
[9'5]
/OH
(I)
/OH
U)
(11)
(ID
0 H
(II)
(I)
0II
0
I!
(e) a / V
3
OH
CH3 - cuf V
3
a)
Xc
ao
^CH2
o f
crH
caf
\ H 22 / XCH3 CH^
3
(I)
O^
a-0
o
c
(II)
CH3
0C__^0
j 0
fj
^ vo
(ii)
CH,
L,
(1)
CHy
2
(II)
CH,
g
CH
OH
...
(IT)
d#52
(1)
(0
'
Ph
^0
(I)
Bansal Classes
O^
^H
Ph
CH
OH
(II)
Ph
CH,
(II)
O7" " f
CH
(I)
OH
(II)
Ph
OH
= NH
($fCH22 = CH - NH2 ^ CH3-CH
^
(II)
(1)
(II)
[10]
Q. 53
In each ofthe following pairs which will have higher enol content:
O
^COOEt
(b) C \
CH 3
CH 3
^COOEt
(c) C \
ft
COO Et
FL
CH 2
"
FL
and
CH 3
CH 2
0
CH 3
CH 3
CH 2
and
Ph
OCH 3
0
II
CH 3
/
CH 2
II
CH 3
OCH 3
'
FL
CH 3
II
Q. 54
CH 3
ft
CH 3
FF
(e)
C O O Et
and
ft
and
II
CH 2
Ph
In each ofthe following pairs which will have less enol content:
^
and Q
( b ) C T a n d Q
and
^ ( ^ f
Q. 5 5 In each ofthe following pairs which will have higher enol content:
II
O
11
(b) (qY \
CH 2 - C H O and CH 2 - C H O
I
NO 2
and
CH 3
y\
CH 3
CI
OH
0
v
> 0
CH 3
( Bansal Classes
0
/
CH 2
CH 3
j
and
c
/ \
CH 3
r
/
CH
^2H5
CH 3
[11]
In each of the following pairs which will have less enol content:
\
/OCH3
(a)
V / O C H
^ 0
O ^ C P
andCP
r.TjJ^
-"Sr
J d ) h > = 0 and
and
h > 0
^ ^ o
(e)
^NO2
(d)(6r0^
II
o
(e)@rH
NH
^
OMe
(d) Ol
I OJ
(e) CH3 - NO
61 what is the relationship between these two molecules? Discuss the structure of the anion that would be
formed by the deprotonation of each compound.
11
->A I
JL
N5" "OH
[12'5]
Q. 62 5,5 - dimethylcyclohexane -1,3 -dione (dimedone) shows tautomerism.Write down tautomeric structure.
Q. 63 Draw enol forms of these carbonyl compounds and comment on the stability of the enol forms.
(a) "
>oo
o
Q. 64 The proportion of enol in a sample of the two ketones below are shown. Why are they so different ?
O
4x
% enol
(b) ( ^ J ^
C H B O ^ ^ - X ^ M I - CH = CH 2
Jf
Q.65 (a)
and
< CU
CH = CH 2
e x "?N :
I
H
What is the tautomeric form ofisatin.
Q. 67
1 , 3 - dicarbonyl compounds such as (A) are usually mostly enolized. Why is this ? Draw the enols
available to compounds A & B comment on the different pattern of enolization.
Q. 6 8 In each of the following sets of compounds write the increasing order of % enol content
JSC
<TI>
(0
(HI)
A
(IV)
(gong;
(I)
(I)
(11)
, i n m
O2N
(IIJ)
N 0
NO 2
[13'5]
(C)
(grv
(1)
(111)
(LI)
NO,
o
NO 2
(111)
(II)
NO,
CI
u^LQj
Q. 69
Ct
(11)
(III)
In each of the following sets of compounds write the decreasing order of % enol content.
O
(a)
0(I)
C(II) O
(IV)
(III)
j a)y
cNr
(III)
(11)
(IV)
j y
(ii)
(1)
o
(e)
ail)
o
(II)
(i)
(d)
(SQ
o.
N"
H
(HI)
(IV)
o
a)
( S | Bansal Classes
(II)
O
(HI)
(TV)
[14]
Q. 70 Enol form of cyclobutanone is very unstable vs enol form of triketocyclobutane, which is very stable.
Q.71
Q-72
CH{
(i)
CD3/
CH3
a
CD3
CH 3
y do
A
\ N
(in)
CH3
J k ^ ?
(Minor)
(Major)
Na0Hl[,H20
O
OH
OH
(Major)
(Minor)
OH
This tautomeric system exist almost exclusively in favour of phenol and it is insensitive to change in
solvent.
[1'5]
ANSWER KEY
Q.2
Q.3
LA b,e LB acdf
(a) 2; (b) 1; (c) 1
Q.5
CH3CH3 + C H 3 C s C M g B r
Q.6
Q.7
Q. 11
Q.14
Q.18
Q.19
Q.20
Q.22
Q.23
Q.24
Q 25
Q.28
Q.29
Q.30
Q.31
Q.32
Q.49
Q.50
Q.51
Q.52
Q.53
Q.54
Q.55
Q.56
Q.57
Q.58
Q.59
Q.60
Q.68
Q.69
Q.72
4g Bansal Classes
[16]
BANSALCLASSES
TARGET IITJEE 2007
ORGANIC CHEMISTRY
XII (ALL)
CONTENTS
EXERCISE-1(A)
EXERCISE 1(B)
EXERCISE-II
EXERCISE-III
EXRECISE - IV(A)
EXRECISE - IV(B)
ANSWER KEY
EXER CISE-IfA)
Q. 1
Q.2
Q.3
Q. 4
(D) Ethane
Acrolein is formed when glycerol is heated with(A) Acidified KMn04 (B) Br2 water
(C) KHS04
(D) HN0 3
Q. 5
Q. 6
When phenol is treated with PC15, the yield of chlorobenzene is generally poor because ofthe formation
of
(A) Benzoyl chloride (B) p-chorophenol
(C) o-chlorophenol (D)Triphenyl phosphate
Q. 7
CICH2CH-CH.2
14
(A) CICH2CHCH2OC2H5
NaOC2H<
14
(B) ClCH2CHCH2ONa
OH
14
(C) CH2-CHCH2OC2H5
fe Bansal Classes
14
(D) CH2-CHCH2OC2H,
[13]
Q. 8
(D)none
Q. 10 Ethanol cannot be dried by anhydrous CaCl, due to formation of the following solvated product
(A) CaCI2-2C2H5OH (B) 2CaCl2-3C,H5OH (C) C a C l ^ C ^ O H (D) CaCl2-C2H5OH
Q.ll
Rate of hydration of
will be in order:
(A) I < II < III
Q.13 The number of methoxy groups in a compound can be determined by treating it with
(A) HI and AgNO,
(B) Sodium carbonate (C) Sodium hydroxide (D) Acetic acid
Q. 14 Most acidic alcohol out of following compounds is
(A) (CH3)3C-OH
(B)CH3CH2OH
(C)CH3OH
Q.15
(D)PhOH
(D)CH 3 -N0 2
Q . 16 A compound 'X' with molecular formula C3HgO can be oxidised to a compound' Y' with the molecular
formula C1H602, 'X' is most likely to be
(A) Primary alcohol
(B) Secondary alcohol (C) Aldehyde
(D) Ketone
Q.17 Diethyl ether and air gives ether hydroperoxide. The mechanism ofthe reaction is
(A) Nucleophilic substitution
(B) Free radical addition
(C) Free radical substitution
(D) None of the above
Q.18 Ether on carbonylation gives
(A) Alkanoic acid
(B)Alkanone
Q. 19
I0R - O- R
i
H
(C)Alkylalkanoate
(D)Alkanal
(D)Sulphonal
[13]
0 .21
Q.22
KHSO,
LiAlH4
Glycerol
A
A and B are :
(A) Acrolein, ally! alcohol
(C) Ally] alcohol, acrolein
Q 23
Q.24
Phenol
(ii)C02/140C
H+/H2
>B
CH3COOH,A
(D) aspirin
In the Liebermann's nitroso reaction changes in the colour of phenol occurs as:
(A) Brown or red-greenish red-deep blue
(B) red-deep blue-green
(D) white-red-green
(C) red-green-white
Q.26
A. 'A'is
CH2OH
CH2OH
(C)
CH,
7 r>cH3
Q.27
cold
I^IJ
>A
alkaline K M N 0 4
"
A and Bare:
CH,
.CH,
OH J ^ ^ O L L
(A)
OH'I
(C)
fa Bansal
CH3
OH
OH '
Classes
CrO,
>B
ACOH
J=0
CH3
OH
[36]
Q.28
r v
NaBH,
B *
CH = CH - CHO
H2/Pt
>A
A and Bare:
(A) (
(B) ^
/ - CH 2 CH 2 CH 2 OH,
(C) (
(D)
CH 2 CH 2 CH0, (
/ - C H = CH-CHJOH
J - CH = CH - CH 2 OH
CH 2 CH 2 CH 2 0H in both cases
CH,
Q.29
B 4r
CH,OH
CH,ONa
CH.-C-CH,
\J
o
"
2 18
>a
H+
A and B are
(A)CH,-C-CH,
18
CH,
CH,
~ 3
CH,
l
3
,CH3-C-CH2
(B) C H 3 - C CH 2 , C H 3 - C - C H 2
OH OCH,
OH OH
CH,
CH,
(C) CH 3 - C - C H , , CH, - C C H ,
IBOH OH
0OH
18
CH,
OHlgOH
OH OCH,
CH,
CH,
(D) C H , - C C H , , C H , - C CH,
OH
3OH
18
OH
OCH 3 OH
Q.30
Oxalic acid + A
henceA
>
^ B , B i s :
0 = ^
(A)
(C)CH2-0-CH2
(B)
OH
fa Bansal
Classes
Alcohols
OH
(D) None
rH=PH_
' CH2CH3
K
0H
Q.31
CH2CH2OH
!IS
HBO
(C) II, III, I
oxymercuration-demercuration
(D) III, 1, II
-OH
OH
OH
(II)
(I)
will be in order
(A) IV > III > II > I
Q 33
II
CI-LMgBr
(TV)
(III)
Mg/ether
> r.
H,0+
F,
E is
(A)
(B)
CH3
CH2I
OH
(D)
(Q
CH,
CH,
CH2CH3
OH
Et
H+ ^ ? Product is:
Q.34
Me
Ox
/Et
(A)
Q 35
/ \ / \ /
CI
Ale. KOH
(A) \ 0 / V ^ / \
(C)
fa B a n s a l
/ \ / \
Classes
(B) H \ q A A
(D)
CJ
x r
[36]
RMgX
Q.36
R'
? P r o d u c t Obtained is:
H2O
R"
R'
(A)R'-C-CH2OH
(B)RCH2-C-0H
R"
R"
(C)R'GH2-C-OH
R"
I,/NAOH
R H
CH,
H+
A )
. .
A, A IS
o
II
o
II
C-OH
(A) <
CH3
\H
(A)
H.CO
OH
&
\H
?PH3
OH
ch
\H
(B)
&
(C)
H
OH
MeO
CH 3
OCOCH3
AICI3
~OCH,
H 2 SO 4
CP 3
Cs
(D)
(C)
<B>pr
(A)
Q.39
R'
OH
Q.37
Q.38
(D)R"CH2-C-OH
>
Of
yj(
OCH,
&
H 3 CO
CH3
CD)"
H 3 CO
OH
HO
CH 3
&
H 3 CO
OH
7 M a j o r P r o d u c t is:
(B) H 3 C O C
()\Or\Oy~OH
COCH,
<!Bansal Classes
O-CH2CH=CH2
Q.40
Y Q Y
^, ? Product is:
OH
OH
/R
R\/
/R
(B)
(A)
CH2CH=CH2
CH 2 -CH-CH 7
OH
R V A / R
(c)
(D) no reaction
iJSiCH2CHCH9
OH
(i)CHCS3+KOH
Q.41
OH
(ii)CH 2 I 2 +NaOH
OH
(A)
j c g f OH
X
HOOC' ^
O H C
\ ^
O H
OCH3
(C)
OHC
l O l
/OH OH
Q.42
(D)
/ H :
OCH3
OHC
Inthisdiol
(A) OH at C2 is more basic than that of at C5 (B) OH at C2 is more acidic than at C5.
(C) both have same basicity
(D) both have same acidic strength
Q.43
(CH3)2C = C(CH3)2
H,O
0H
~ >B
(A) (CH3)2C-C(CH3)2
O
(C) (CH 3 ) 2 C-C(CH 3 ) 2
I I
OH OH
Q.44
OH
CH 2 -NH,
NaNO,
HCl
(D) None
>A
A is
OH
CH-,-OH
(A)
i&Bansal Classes
OH
(B)
CH2-C1
OH
CH 2 -NO,
( C ) f l
( D ) f S
fSJ
Q.45
CH 2 =CHCHCH 2 CH 2 OH -
Mn0
--
)A.Ais
OH
(A) CH 2 = CHCCH 2 CH 2 OH
OH
o
(D) CH 2 = CHCCH 2 COH
Q4b
Acetophenone
HCO,H
2
o
+
H,0
2
> A
>B + C
PthalicAnhydride
C & D are
X
(A)CH3OH&(^Xc><J
(B)PhOH&[0
OPh
II
0
o
II
OH
(D) CH 3 OH & [ O
C-CH3
C-CH3
C-
II
o
V- lo
Q. 47
/OH
m-Aminophenol on treatment with NaOH and C 0 2 gives which of the following as major product?
COOH
H,
OH
(A)
(B)
L J
(C)
XOOH
^Y^COOH
NH,
COOH
OH
f ^ Y
(D)
Question No 48 to 50 (3 questions)
500C No reaction
LiAlH 4
NaBH,
Q.48
COOH
Compound 13'is?
(B) ^ J - C O O H
(A)'
fa Bansal
Classes
(C) ^ e ^ - C H 2 - O H
(D) ( ^ T n j h c i i j
[36]
(C)3
(D)6
EXERCJSE-I(B)
Q. 1
(B) M e - C - N H ,
II
O
Q.2
Q. 3
II "
o
(C) M e - C H - C H 2
H2
>A
' B
II
II
(D) M e - C - O C - M e
(D)NaOH
C , true about the product C is
(C)
, ,
11
y / , (
OH
Q5
11
(D) CH3CCH2CHCH2CCH3
'OH
\qh
HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in
(B)
Q. 6
OHO
I H
(B) CH3CHCCH2CH3
fe Bansal Classes
(cO
(dO
[13]
Q.7
(D) ( C ^ B r + (CH3)3CONa
Q.8
Q.9
Q. 10
> (CH3)3CO-^o)
(D) liq. NH 3
(B) Aldehyde
(D) Alkene
HC1
c0nc
anhydrous ZnCl 2
>
R C j
White turbidity
Q. 12
(!Bansal
Classes
(B) Oximinoacetone
(D) dimethyl amine
[U]
(A)
CH 3
/Urn
H
0 T CH
CH3OH
H2S 4
3
CH;
CH;
\ , \ ~ ~ K/
rm
(DJ
H | O
CH,OH
CH 3
O /
(C) This is only affected in reduction to 2 alcohol
O
H+
"
R-C^OH + HtO-R
(D)
Q.15
0 H
+HN0 3
2s4
>
2s4
NO,
Q-ONO.
(D) ~
Q.17
>
-OCH
Dehydration of alcohols take place more rapidly with POCl3 than with H,S0 4 . Select the correct
statement(s) about the following dehydration reaction.
Is.
j )
pyridine
Classes
[36]
Q.18 Which of the following will get oxidised by Br2 / KOH into carboxylic acid?
(A) CH3-CH2-OH
(B)
CH - CH3
OH
(C) ( ^ y - C H 2 O H
(D)
<
CII,
A.
CH,
OH
OH
OH
CHO
C A ) ^
( B ) ^
CH3
(C) ^
c h o
CH3
.(D)
CH3 CHO
CH
Q .22 For the reactions shown below, identify the correct statements) with regard to the products formed:
(i)
ph
*>\y0
(h)
ph
^\7
Tilden
reagent
(A) Alcohol
fe Bansal Classes
> (i)
NH
? > (ii)
HC1
[13]
Q 24
(A)f
Q. 25
(B)(
.OH
/
cy
\>H
(D)
(C)|
O
(B) It is more acidic than CH 3 COH
(D) It is a diacid base
Mechanism
OH
(A)
CH=CH ? "
(P)
(Q)
Pinacol rearrangement
(R)
(S)
Ketone as product
CH 2 ~OH
(B)
OH
CH3CH3
3
(C)
OH
heat
>
O-CH,
<P)
Q. 27
& Bansal
Classes
(P)
(Q)
(R)
Column II
Oxymercuration demercuration
Cu/300 heat
Victor Mayer's test
(S)
Hydroboration oxidation
(i)
Lucas test
[14]
Q.28
(P)
Column H
KMn0 4 /A
(B)
Cr0 3 L
(Q)
Collin's reagent
(C)
Cr0 3 .2
(R)
Jone's reagent
(S)
P.C.C
N'
U .HC1
(D)
Q.29
< 0 > 0 - C ,
Column II
^ 0 >
(?)
(0>i
(Q)
{ o >
CH
2 - OH
OH
(R)
LiAlH 4 /H 2 0 gives
(D)
Q.30
f n l + K i > ?
CH, - CH - CH = CH 2
(S)
<OVCH2-I
ReageatR^ Alcohol
CH 3
which is true about alcohol and R?
Alcohol
Reagent
(A)
B2H6,H202/Na0H
CH , - CH - CH 2 - CH 2 OH
"I
CH,
CH3-CH-CH^CH3
(B)
CH 3 OH
PdCl2, H 2 0, 0 2 / LAH
OH
(O
CH3--C-CH2CH3
CH 3
OH
(D)
CH3-C-CH2CH3
dil. H2S0 4
CH 3
fa Bansal
Classes
[36]
EXER
Q. 1
Q.2
H02C(CH2)4"C0Cr->
(c)
(d)
(e)
(f)
(g)
0 2 N(CH 2 ) 2 CN
-> 0 2 N(CH2) 2 CH 2 NH 2
0 2 N(CH 2 ) 2 CH = CH2 -> H2N(CH2)2CH=CH2
Me2CHCOCl -> Me 2 CHCHO
0 2 N(CH 2 ) 3 CH0
0 2 N(CH2) 3 CH 2 OH
0 2 N(CH 2 ),CH=CH 2 -> 0 2 N(CH 2 ) 3 CH 3
H02C-(CH2)4CH20H
Following compounds undergoes reaction with Mn0 2 . What are the products in each case?
(a) CH 3 CH 2 CH=CHCH20H
(tyPhCI^OH
(c) PhCH(OH)CH 2 CH 2 OH
(d)MeCH=CH(CH 2 ) 3 OH
Q. 3
CISE-II
(e) [ ^ > - O H
(i)
Br
Acraldehyde
Br - CH, CHO
(iii)
/CHO
MeO'
Glyceraldehyde
Ph CHOH CH2 CHO
O
(iv)
-CH 2 OH
CO,Et
(v)
Glyceraldehyde
Q. 4
mild
^ ^ C I L C O J I
C6H120
(A)
Q.6
Product
Explain product formation. How two OH groups behave differently.
Q.7
fa Bansal
Classes
[36]
OH
Q.8
What are A to E?
TsCl
Pyridine
NaBr
Mg
dry ether
Q. 9
D-S2-B
1.CHJCHO
2. HjO
(i)
Me 2 CO+A
Me2C.
\
o-J
(i)
1.HCO3H
(iv)
2.H20
Q. 10 What are the order of rates of oxidation with HI0 4 ofthe following diols. Explain with reasons.
(a)Me 2 C(0H)C(0H)Me 2
(b) Me2C(OH)CH (OH) Me
(c) CH2(OH) CH2 (OH)
(d) Me CH(OH) CH (OH) Me
Q. 11 t- Butanol in presence of fenton's reagent forms 2,5 dimethyl hexane 2,5 diol as one of the product.
Explain with the mechanism.
Q. 12 How you distinguish the following compounds?
(a) t butyl alcohol & n butyl alcohol
(b) ethyl alcohol & n propyl alcohol
(c) allyl alcohol & n propyl alcohol
(d) benzyl methyl ether & benzyl alcohol
Q.13 Differentiate:
(a)
1 -Hexanol and 1 -chlorohexane
(c)
Diethyl ether and n-pentane
Q.14 Explain:
(a)
No est erifi cation takes place between ethyl alcohol and excess of sulphuric acid at 170C.
(b)
Sodium chloride solution in water is added to decrease the solubility of organic compounds in water.
Q.15 Predict A, B & C.
CH3OH -
P+L2
>A
+C
Q. 16 Carry out conversion of methyl alcohol into ethyl alcohol and vice versa.
^Bansal
Classes
PV
Q.17
Arrange the compounds (i) Ethanol, propane and 1-pentanol, (ii) Butane 1,2,3-pentanetriol and butyl
alcohol, (iii) Pentane, 1 -pentanol and 1 -hexanol, on the basis of (a) in order of increasing boiling points
and (b) in order of increasing solubility in water.
>?
pressure
Me2CO + EtMgl
(iii)
EtC02Et + 2MeMgI
(iv)
(^
/=CHCO,Et
/ /=CHC0
2 Et
H+
>?
>?
>?
T T
> ^\ = C^=CHCH
T
2OH
Mn0?
Q. 20 t-butyl alcohol reacts less rapidly with metallic sodium than the primary alcohol. Explain why?
Q. 21 Diethyl ether behaves as base. Why?
Q. 22 What is the significance of proof spirit?
Q. 23 Sodium metal can be used for drying diethyl ether but not for ethanol. Why?
Q.24
Sometimes explosion occurs during distillation of ether sample. Give the reason.
Ag20
>B
Q. 27 Ethyl alcohol reacts with HI but not with HCN. Explain why?
Q. 2 8 Write the structure ofthe principal organic product formed in the reaction of 1 -propanol with each of the
following reagents:
(i)
Potassium dichromate (K2Cr207) in aqueous sulfuric acid, heat
0
II
(ii)
(iii)
CH3
(iv)
OO
fe Bansal Classes
[13]
o
m
(v)
Presence
pyridine
Q. 29
Complete the following series of equations by writing structural formula for compounds A through I:
(a)
^\\ J j//
\\
HCl
C
//
NaHC
C ?HCf J1
5 H
> S 7
3 ) C H O
5
Compound A
(b)
CH, = CHCH,CH,CHCH,
1
SOC 2
'
Compound C
> C,H,,C1 ^
pyridine
> r HXIO
(ii)Zn/H20
> Compound G
'
> C5 H 6 O
(D)
^ ^ N ^ P H
*
H2S04,H20
Compound B
OH
(c)
NaB 4
"
>CH,,(
5
(E)
'
e.
11
(F)
Compound H
'
> Compound I
CH,C1,
heat
Q. 3 0
(a)
Predict the principal organic product of each of the following reactions. Specify stereochemistry where
appropriate.
/Br
- ^ ( A )
methanol
H;C
(b)
|>
+ CH 3 ONa
CH3 H
>(B)
CH2C6H5
(c)
(d)
Q. 31
Deduce the identify ofthe missing compounds in the following reaction sequences. Show stereochemistry
in parts (b) through (d).
(a)
CH2 = CHCH 2 Br
VCH-CH2
> (D)
compound A(C4HgO)
(iii)H,0
g
DC
compound D <
compound C (C 4 H 7 BrO)
COoH
(b)
(1)
ClCH,
^Bansal Classes
K0H H
'
[19]
Q. 3 2
(a)
(b)
(c)
(d)
Choose the reaction in each ofthe following pairs that proceeds at the faster rate. Explain your reasoning.
Base-promoted hydrolysis of phenyl acetate or m-nitrophenyl acetate
Base-promoted hydrolysis of m-nitrophenyl acetate or p-nitrophenyl acetate
Reaction of ethyl bromide with phenol or with the sodium salt of phenol.
Reaction of ethylene oxide with the sodium salt of phenol or with the sodium salt of p-nitrophenol
(e)
Q. 3 3 Explain why ArOR ethers are cleaved to give RI and ArOH rather than Arl and ROH.
Q.34 Explain the mechanism of following:
(iii)
(iv)
R'
R
OH
0-CH 7 -CH=CHR
CH 2 -CH=CHR
CH=C-CH 3
CH=CH-CH 3
(v)
Me
Q.37 Give the product of the reaction ofPhjCHC^OH with HBr and explain its formation.
Q.38 Give the product and write a mechanism for the acid dehydration of cyclobutylcarbinol.
Q.39 C2H5OH
PC 5
'
Q.40 CH3CH2CH20H
fe Bansal Classes
> (A) -
KCN
(A)
> (B) -
->(D)
->(C)
->(B)
(E)
+ (C)
[13]
EXERCISE-III
Q. 1
Compound (A) gives Lucas test within 5 minutes. 6g (A) when reacts with Na, 1120 mL of H2 is
generated at STP. fA) having one oxygen per molecule. What is the structural formula of (A)? Compound
(A) when treated with PBr3 gives (B) which when treated with benzene in presence of anhydrous A1C13
gives (C). What are (B) and (C)?
Q.2
An open chain compound (A) C5HgO is optically active. When (A) is hydrogenated in presence of Pd
as catalyst, it absorbs two moles of F^ per mole of (A) to produce compound (B) C 5 H 12 0 which is
optically inactive. However when (A) is warmed with dilute E^SC^ in presence of HgS04 it gives
compound C(C5H10O2) which is still optically active. C responds to iodoform test. What are the structures
of A to C?
Q .3
An organic compound (A) C10H12O gives red colour when treated with cerric ammonium nitrate & also
decolourises Br2 in CC14 to give B (C10H12OBr2). A can show both geometrical & optical isomerism. A
on treatment with L, & NaOH gives iodoform & an acid (C) after acidification. Give the structures ofA
to C & also the stereoisomers ofA.
Q. 4
A(C7H]4) decolorises Br2 in CC14 reacts with Hg(OAc)2. THF-NaBH4 to form B (resolvable compound)
A C < K M n Q ^ - 3 hexanol
2.Zn/H20
D (isomer ofA)
D (isomer ofA)
l.B 2 H 6 .THF
2 H 0
1
/0H-
>
>G<
E (chiral)
YMaD
KMn0 4 /alkaline
2 m e t h y l
2.Zn/H20
3 pen tanol
Find out A to G.
Q. 5
Suggest short, efficient reaction sequence suitable for preparing each of the following compounds from
the given starting materials and any necessary organic or inorganic reagents.
(0
(iii)
CH2OCH3 from
- COCH,
(ii)
frombromobenzene
and cyclohexanol
OH
(iv)
(v)
(vi)
OH
Q.6
A compound (X) reacts with thionyl chloride to give a compound (Y). (Y) reacts with Mg to form a
Grignard reagent, which is treated with acetone and the product is hydrolysed to give 2-methyl-2-butanol.
What are structural formulae of (X) and (Y)?
fe Bansal Classes
[13]
Q. 7
The compound (D) reacts with BH3- Tetrahydrofuran and then alkaline H 2 0 2 to give chiral (E). Oxidation
of (E) with KMn04 (acidified) gives a chiral carboxylic acid (F). Ozonolysis of 'D' gives after reduction
with Zn the same compound (G), which is obtained by oxidation of 2-methyl-3 -pentanol with acidified
KMn04. Identify (D), (E), (F) and (G).
Q. 8
An organic compound (A) contains 60.12% Carbon, 13.13% Hydrogen and has vapour density 3 0. On
oxidation it gives (B) C 3 H 6 0 which on further oxidation by NaOH +12 produces a salt of the acid (C)
C2H402. When (B) is treated with hydroxyl amine, a compound of molecular formula C3H7NO (D) is
formed. What are (A), (B),(C) and (D)?
Q. 9
Compound (A) C 4 H |0 O reacts rapidly with metallic sodium, but undergos almost no reaction with
Lucas reagent. When (A) is treated with hot concentrated sulphuric acid, a new compound (B) C4H8 is
formed. If C4Hg is hydrated with sulphuric acid a new compound (C) C4H9OH is formed, which is
almost inert to metallic sodium but reacts rapidly with Lucas reagent. What are (A), (B) and (C)?
Q. 10 A compound (X) containing C, H and 0 is unreactive towards sodium. It does not add bromine. It does
also not react with Schiffs reagent. On refluxing with an excess ofHI, (X) gives only (Y). (Y) on hydrolysis
gives (Z) which can be converted to (Y) by the action of P +12, Compound (Z) on oxidation gives an
acid of equivalent weight 60. What are (X), (Y) and (Z)?
Q. 11 A compound (A) C ; H lf) n^ yields on acetylation (B) of formula C12H1808. How many hydroxyl groups
are present in compound? A l s o write structures of (A) and (B).
Q. 12 An optically active alcohol (A) (C6H10G) absorbs two moles of hydrogen per mole of (A) upon catalytic
hydrogenation and gives a product (B). The compound (B) is resistant to oxidation by Cr0 3 and does
not show any optical activity. Deduce the structures of (A) and (B).
Q.13
An unsaturated hydrocarbon (A) on hydration gave alcohol (B). Oxidation of (B) gave a ketone (C).
When the hydrocarbon (A) was submitted to ozonolysis it gave formaldehyde and acetaldehyde. What
one formula would you assign to A, B and C? Give the reactions involved.
Q. 14 Compound (A) reacts with sodium to liberate H2 forming a compound (B). When (A) is treated with
HC1 + ZnCl2, an immediate reaction takes place liberating (C). When (A) is heated with H2S04, (D) is
formed. Ozonolysis of (D) gives a three carbon ketone and another isomeric compound. What are (A),
(B), (C) and (D) ?
Q.15
An organic compound (A) (C4H]0O) reacts with HI giving a compound (B) (C4Hgl) which on reduction
gives a normat hydrocarbon having four carbon atoms. On oxidation A gives compound (C) (C4HgO)
and then an acid (D) (C4H802). Deduce th structures of, B, C and D giving reasons.
Q. 16 An organic compound (A) gives hydrogen on reacting with sodium. It also gives iodoform test and forms
an aldehyde of molecular formula (B) (C2H40) on oxidation. Name the compound (A) and (B).
Q.17 An organic compound (X) on analysis gives 24.24% C, 4.04%H. Further sodium extract of 1.0 g of (X)
gives 2.90 g ofAgCl with acidified AgNO, solution. The compound (X) may be represented by two
isomeric structures (Y) and (Z). (Y) on treatment with aqueous KOH solution gives a dihydroxy compound,
while (Z) on similar treatment gives ethanal. Find out (X), (Y) and (Z).
fe Bansal Classes
[13]
Q.18 Compound (X) (C5HgO) does not react appreciably with Lucas reagent at room temperature but gives
a precipitate with ammonical silver nitrate. With excess ofMeMgBr, 0.42 g of (X) gives 224 ml CH4 at
STP. Treatment of (X) with H2 in presence of Pt catalyst followed by boiling with excess HI gives
n-pentane. Suggest structure for (X) and write the equations involved.
Q. 19 An alcohol (A) when heated with concentrated H^SC^ gives an alkene (B). When (B) is bubbled through
bromine water and the product obtained is dehydrohalogenated with excess of sodamide, a new
compound (C) is obtained. The compound (C) give (D) when treated with dilute H^SC^ in presence of
HgS04. (D) can also be obtained either by oxidising (A) with KMn04 orfromacetic acid through its
calcium salt. Identify (A), (B), (C) and (D).
Q. 20 Compound (A) contains only carbon and hydrogen. It decolorizes bromine in CC14 solution and reacts
slowly with concentrated HjSO^ Compound (A) reacts withHBr to form (B). (B) reacts with NaOH
to form (C). (C) on oxidation gave hexanone-3. Write structures of (A), (B) and (C).
Q. 21 A hydrocarbon (A) (molecular formula C5HJ0) yield 2-methylbutane on catalytic hydrogenation. (A)
adds HBr in accordance with Markownikoff s rule to form a compound (B), which on reaction with
silver hydroxide forms an alcohol (C) C5H120. Alcohol (C) on oxidation gives a ketone (D). Deduce
(A) to (D) and give the reactions involved.
Q.22 (A)
'
250C
(Vb ) ._JiM_> ( c)
> (ii)AgOH
'
150C
(^-Wk^A)
' (ii)H202,0H-
'
In the above reactions scheme (A) and (C) are isomers. (B) has a formula of C5H10. (C) Can also be
obtained from the product of the reactions of CH3CH2MgBr and (CH3)2CO. Give structures of (A),
(B)and(C).
fe Bansal Classes
[13]
EXERCISE-IV (A)
Q.l
l O j
+ C0 2 >
x -J*"-*
w(OJ
<B)(OJ
(O^J
(D)glC00Ni
Q.2
Q. 3
An organic compound C 3 H 6 0 does not give aprecipitate with 2,4-dinitrophenyl hydrazine reagent and
does not react with sodium metal. It could be:
[JEE 1993]
(A) CH3-CH2-CHO (B) CH3-CO-CH3
(C) CH2=CH-CH2OH (D) CH2= CH-OCH3
Q .4
Q5
CH3
0 H
U)
CH 3
Ph
OH
OH
(IV)
an)
(II)
[JEE 1997]
CH 3
o nI
CH 3
(D) CH,OH
Q.7
Q. 8
Which one of the following will most readily be dehydrated in acidic condition:
0
Q.9
OH
AA
V
A
X
OH
cb) A
/
Classes
* [JEE 1998]
[JEE 2000]
YX
0 H
fe Bansal
[JEE 1992J
0 H
[JEE2001]
[13]
Q. 10
Q.ll
< O ^ O H
C2H5I
(A) < 0 } - O C 2 H 5
O Na+(excess)
[JEE 2002]
[JEE 2003]
; OH(anhydrous)
< B ) @ - I
(C)C 6 H 5 OC 6 H 5
(D)C 2 H 5 OC 2 H 5
Q. 12
Reaction of entainomerically pure acid with 1 chiral carbon and racemic alcohol with 1 chiral carbon
[JEE 2003]
gives an ester which is:
(B) Optically active mixture
(A) Meso
(D) Enantionmerically pure
(C) Racemic mixture
Q.13
Q. 14
[JEE 2005]
CH,
(A) Ph - OH
Q.15
(B) P h - H
(C) Ph-0-C~C:H 3
CH
Q. 16
[JEE 2004]
/CH3
( D ) PI1-C-CH3
\ CH,
[JEE 2005]
(D)HCl + ZnCl2
CH 3
CI CH 3
following products:
CH3H
CH3O-<O)
-<Q>NO2(K)
H
O-^>
-^(O)-N02(L)
OH H
CH 3
-N0 2 (M)
H
Classes
CH 3
CH 3
CH 3 O-
^Bansal
CH
OHCH 3
CH3H
(A) K, L
CH3H
CH 3
CH 3 OH
(B) K, M
(C) L only
Alcohols & Ethers
(D) M only
[JEE 2005]
[25]
Q 17
+ CI - CH 2 CH 2 - CH 3
^ ^
> Q + Phenol
[JEE 2006]
(A)j^andCH3CH2CHO
(C)fSandCH3COCH3
i
1I
I ]
!
feBansal
Classes
When t-butanol and n-butanol are separately treated with a few drops of dilute KMn04 in one case
only, purple colour disappears and a brown precipitate is formed. Which of the two alcohols gives the
above reaction and what is the brown precipitate?
[JEE 1994]
(XZ
Q.3
A compound D (CgH10O) upon treatment with alkaline solution ofiodine gives a yellow precipitate. The
filtrate on acidification gives a white solid (E) (C7H602). Write the structures of (D) and (E) and explain
the formation of (E).
[JEE 1996]
Q. 4
(i)
Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(CH3)3CBr + NaOMe
>
(ii)
CH3Br + tert-BuONa
> [JEE 1997]
Q.5
O = C-OH
HOCH2
I
+
I
O = C-OH
HOCH2
[JEE 1997]
Qj /
Discuss why o-hydroxy benzaldehyde is a liquid at room temperature while p-hydroxy benzaldehyde is
a high melting solid?
[JEE 1999]
Q.7
[JEE 2000]
3
2
>. A+B
O
Q.8
Cyclobutyl bromide on treatment with magnesium in dry ether forms an organometallic A. The
organometallic reacts with ethanal to give an alcohol B after mild acidification. Prolonged treatment of
alcohol B with an equivalent amount ofHBr gives 1 -bromo-1 -methylcyclopentane (C). Write the structures
ofA, Band explain how C is obtained from B.
[JEE 2001]
Q. 9
Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H2C*0) as one of the products when compound Z is treated with HBr and
subsequently ozonolysed. Mark the C* carbon in the entire scheme.
[JEE 2001]
BaC*03 + H 2 S0 4
> X (gas) [C* denotes C14]
CH2 - CH - Br
Q.10
^ M * /ether >y
(ii)X,(iii)H,0+
LlAm
-* >Z
Mention two esters produced when a racemic mixture of 2-phenyl propanoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters?
[JEE 2003]
Q. 11 An organic compound P(C5H10O) Reacts 1015 times faster then ethylene with dil.H2S04 to give two
products Q and R. Both Q and R give positive iodoform test. Identify P, Q and R and also give reason
for very high reactivity of P.
[JEE 2004]
Q. 12 (X) C5H!3N
NaNo 2 ,HCi
-N2
> (Y)
(Optically active)
Find X and Y. Is Y optically active? Write the intermediate steps.
fe Bansal
Classes
[JEE 2005]
[13]
ANSWER KEY
EXER
Q.IQ.8
Q.15
Q.22
Q.29
Q.36
Q.43
Q.50
B
C
B
A
A
B
A
A
Q.2
A
Q.9
D
Q. 16 A
Q.23 B
Q.30 A
Q.37 A
Q.44 D
Q3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
C
c
B
D
C
B
A
CISE-I(A)
B
A
C
A
C
A
C
EXER CISE-I
Q.l
Q.5
Q.9
Q.13
Q.17
Q.21
Q.25
Q.27
Q.29
Q.3
A,C,D
Q.2
C
Q.7
A,B
Q.6
A, B,D
Q.ll
Q.10 A,B,D
A,D
Q.15
Q.14 AB,C,D
A,B,C,D
Q.19
Q.18 A,B
A,B,C
Q.23
Q.22 C,D
A,C
A,B
Q.26 (A) P, Q, S; (B) R,S;
(A) Q,R,T, (B) R, (C) S, (D) P
Q.28
(A) R, S; (B) R; (C) Q; (D) P
Q.30
EXER
Q2
Q.5
Q. 12
Q. 19
Q.26
Q.33
Q.40
Q.47
B
C
D
B
D
A
C
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
D
A
C
A
D
C
C
Q.7
Q.14
Q.21
Q.28
Q.35
Q.42
Q.49
Q.4
Q.8
Q.12
Q.16
Q.20
Q.24
B
A,B,C
A,B,C
A,C,D
A
A,B,C,D
D
C
D
B
D
A
C
(B)
A,C
A,B,C
A,C
A,B,C
A,B,C,D
(C) P ; (D) S
(A) Q,R,S (B) S (C) Q (D) P
A,B,D
CISE-II
O
Ii
(c) Ph - C - CH 2 - CH 2 - CH
(e)
OCH 3
OCH3
Q. 4
In acidic medium Me 2 - C - CH 2
and
In basic medium Me 2 C - CH 2
OH
Q.5
(A)
CH3-C-O-C-C-C-C,
(B) C H r C H 2 O H ,
(C)
CH3-CH2-CH2-CH2-OH,
O
OH
O
II
i
II
(D) C H , - 0 - H , ( E ) CH3- CH - C H - C H O (F) CH - C H = C H - C - H
faBansal
Classes
[28]
Q.9
(A) =
C H
- O H
CH 2 -OH
Q.10 a > b > d > c
Q. 12 (a) Lucas reagent
(b) Iodoform
(c) PBr3 & AgN03
(d)Na
Q. 13 (a) 1-hexanol reduces organ red Cr0 3 to greenCr3^ while 1-chlorohexane gives white ppt. ofAgCl on
warming with ethanolicAgN03.
\
(b)
n-Butanol gives a positive test with Cr0 3 in acid and evolves H2 with sodium: while dry ethyl etheris
negative to both tests
(c)
Unlike n-pentane, diethyl ether is basic and dissolves in conc. f^SC^
> (C2H5)2OH++ HSO"
(C2H5)20 + H ^
Q.14
(a) Ethyl alcoholfirstreacts with sulphuric acid to form ethyl hydrogen sulphate which readily lo ses a
molecule of sulphuric acid when heated with concentrated sulphuric acid at 170C to form ethylene,
(b)
When sodium chloride is dissolved in water it reduces the polarity ofwater the space between water
molecuules are occupied by sodium and chloride ions with the result the solubilty ofthe organic compound
is reduced.
Q.15 CH3I, CH 3 -0-CH 3 , CH3I
Q.16
CH
OH
p+12
CH,I
KCN
CH
CN
reduction
CH
CH
NH
HONO
Methanol
Ethano!
CH3OH
Q.17
(b)
KOH(aq.)
CHGCL
C1
' CH,
fe Bansal Classes
[13]
Q.18 (i)
The reaction is SN2 the smaller group forms the iodide (steric effect) & stops at thefirststage in the cold.
When heated, the reaction proceeds to the second stage.
(ii)
(iii)
W
Me, = CH,
Q. 19 (i)
h s
2 4-h2
pressure
n - C3H7C02H
Me2CO + EtMgl
(iii)
EtC02Et + 2MeMgI
CHC0
orB2H6
Pressure
2Et
H+
IMgOx / M e
>
C
EtX XMe
LiA1H4
> Me 3 C-0-CMe
3
+
> n - C4H9OH
/OMgl
>M 2 C<^ E t
(ii)
(iv)
Me3C H
> M e 3C +
> MeXCOH)Et
"2
EtCMe2OH
>^^CHC^OH
Mn 2
> (^^CHCHO
Q. 20 The +I.E. of three methyl groups on central C-atom oftert-butyl alcohol makes is partially negative with
the result that it pushes the electron pair of -OH bond towards H-atom and thus H-atom is not replaced
easily.
CH3
^
- 5 + 0
CH3"^ C
'
-6
+8
0-- H
CH3
^ > 0 : + HC1
Q.22 Proof spirit is a technical term representing 57.1 % by volume ethanol-water mixture for the purpose of
tax lavied on its production. The percentage represents the weakest possible percentage which allows
the gun powder to catch fire.
Q. 23 Sodium metal reacts with ethanol to form sodium ethoxide ion because of active H atom in ethanol. Ether
do not have such active H and thus can be dried by sodium
C2H5OH + Na
> C2H5ONa + - H 2
^Bansal Classes
[30J
Q.26
Q.27
Ethanol being very weak Lewis base and thus reacts with stronger acid HI
Q.28
(i)
CH3CH2COOH
(iii) MePhS020CH2CH2CH3
(ii) CH3COOCH2CH2CH3
O
(iv) PhCOOH + PhCOOCH2CH2CH3
OH
Q.29
(A)\^J
-CH 2 CH 2 CH 3
(v)
(c)
( B ) ^
CJ
(E) CH3CH(C1)CH2CH2CH0
CH?OH
Q.30
(a)[Ol
Br
NFL
r 2
OMe
(b)
CH2Ph
(c)Ph-CH(Cl)-CH 2OH
Me' t)H
OH
(d) H 3 C-CH 2 -CH 2 -CH 2 -S-CH 2 -(CH 2 ) 16 -CH 3
Q.31
(B) Bi-CH2CH(Br)CH2CH2OH
CH 2 OH
CI|
Me
( F ) Me-CH-CH 2
Q.33
S n 2 attack on a carbon of a benzene ring does not occur nor does the high energy C6H5+ form by an
SN1 reaction. Hence ARL cannot be a product even in an excess of conc. HI
Q.36
(a)
(b)
<
Ph
Q 37
Ph - C - CH3
fe Bansal
Br
Classes
[13]
38
^" / v
V-Cli-,OH
>
Q.39
(A) C2H5C1;
(E) C2H5CONH2
(B) C2HSCN;
(C) C2H5COOH;
(D) C2H5COONH4
Q.40
(A)C3H7Br;
(B) CH3CH=CH,
(C) CH3CHBrCH3
(D) CH3CHNH2CH3
EXER
CISE-III
OH
Q.l
Q.2
A: CH3 - CH - CPI3
H
H O
I
OH
OH
OH
OH
Q3
I!
Br
OH
Q4
CH3
1!
(A) C - C - C - C - C - C , (B) C H 3 - C H 2 - C - C H 2 - C H 2 - C H 3 , ( C )
II
C-C-C-C-C-C
OH
CH2
CH3
II
CO
I .11
C2H5OH
Ethyl alcohol
(X)
(!lBansal Classes
C2H5C1
Ethyl chloride
(Y)
[32]
H
Q.7
CH3-CH-C-CH2OH
C H 3 - C H - C = CH 2
CH 3 C 2 H 5
(E)
CH 3 C 2 H 5
(DJ
H
CH3-CH-C-COOH
CH, - CH - C = O
CH 3 C 2 HJ
(F)
Q.8
(CH 3 ) 2 CHOH;
CH 3 C 2 H 5
(G)
CH 3 COOH;
CH 3 COCH 3 ;
CHGCCHG
NOH
(A)
(D)
(C)
(B)
Q.9
Q.10
C 2 H 5 OC 2 H 5 ;
(X)
Q.ll
(CH 3 ) 3 COH
(C)
(CH^C-CH^
(B)
C 2 H 5 OH
(Z)
C 2 H 5 I;
(Y)
CH 2 OCOCH 3
CHOCOCH,
CH 2 CH CH CH 2
CHOCOCH,
OH OH OH OH
(A)
Q. 12
CH 2 OCOCH 3
(B)
C2H5
C2H5
H X - C - C = CH
CH 3 CCH 2 CH 3
OH
(A)
Q.13
CH 3
Vc
OH
n(B)
\ H
(A)
fa Bansal
Classes
CH 3 CH CH 3
OH
(B)
CH 3 C CH 3
o
(C)
[36]
Q.14
CH 3 CH 2 CH 2 C(CH 3 ) 2
CH 3 CH 2 CH 2 C(CH 3 ) 2
CH 3 CH 2 CH 2 C(CH 3 ) 2
CI
ONa
(B)
OH
(A)
(C)
CH 3 CH 2 CH = C(CH 3 ) 2
(D)
(B) CH 3 CH 2 CH 2 CH 2 1
(D) CH 3 CH 2 CH 2 COOH
Q.15
(A) CH 3 CH 2 CH 2 CH 2 0H
(C) CH 3 CH 2 CH 2 CHO
Q. 16
(A) CH 3 CH 2 0H
(B)CH 3 CHO
Q. 17
(X)C 2 H 4 C1 2
(Y)C1CH2CH2C1
Q.18
CH 2 CH 2 CH 2 C = CH
(Z)CH 3 CHC1 2
OH
(X)Pent
4-yn-l-ol
CH,
Q.19
(A)
\CHOH
(B) CH 3 -CH=CH 2
(C) C H . C . C H
(D) CH 3 COCH 3
C H /
Q 20
+1IBR
> CH 3 - CH 2 - CH 2 - CH - CH 2 - CH 3
Br
(B)
(A)
CH 3 - CH 2 - CH 2 - CH - CH 2 - CH 3
OH
(C)
Q.21
(A) CH 2 =CH-CH(CH 3 ) 2
(B) C H 3 - C H - H C ( C H 3 ) 2
Br
(C) C H 3 - C H C H ( C H 3 ) 2
(D) CH 3 CO CH(CH 3 ) 2
OH
OH
Q.22
(A)HO-C-C-C-C
faBansal
Classes
(B) C = C ' - C - C
(C)C-C-C-C
[36]
EXERCISE-IV (A)
Q.2
B
Q.7
B
Q. 12 B
Q.3
Q.8
Q.13
Q.4
Q.9
Q.14
D
A
D
Q.5
Q.10
Q.15
A
C
B
C
B
C
Q.l
Q.6
Q.ll
Q.16
D
D
D
A
Q.l
n-butanol is oxidised by KMn0 4 and not t-butanol as the latter does not contain H atom attached to
carbinol carbon atom.
EXERCISE-IV (B)
Brown
CH 3
CH3-C-CH3 +KMn04
> No reaction
OH
t-Butanol
H
Me
Q.2
H
H+
CH3-C C-CH3-
Me
-> C H 3 - C C - C H 3
1
- 2 > C H 3 - C H - C - C H 3
Me
HIOH Me
:OH Me
1,2-methyl shift
Me
Me
C H 3 - C = C - C H 3 <-
-H+
Me
Q.3
Me
CH, - CH - C - CH,
i |
+ J
Me
(D) Ph - CH - CH 3
(E) C fi H,COOH
OH
Q. 4
The ether formation involves nucleophilic substitution of alkoxide ion for halide ion.
R'0~+R-X
R'0~+R
Slow
->R' 0
X - ^ R ' - O - R + X-
3 alkyl halide can also involve elimination ofHX to give alkene in the presence of a base. So, it is better
to start with 3 alkoxide and 1 alkyl halide, i.e., equation (b)
Q.5
Q.7
A = C H 3 - C - 0 H , B = C2H5018H
Q.6
fa Bansal
Classes
[36]
Br
MgBr
BrMgOCHMe
Mg
Q.8
MeCHO .
HOCHMe
Br
Me
H,0
(A)
(B)
(C)
Mechanism
CHMe
H-,0 CHMe
HOCHMe
Br
Me
Br~
2carbonium
Q.9
3 carbonium
X : C O , ; Y : C H , = C H - C O O H ; Z : CH,2 = C H C H -2O H ; C H , 0
RCT+RQC
Ph
Q.10
(+)CH 3 CH 2 -C-OH
CH3
CH 3 - C - COOH + CH 3 - C - COOH
conc. H,SO a , A
Ph
H
(recemic mixture)
Ph
CH, - C - C - O - C - CH 2 CH 3 + CH 3 - C - C - O - C - CH 2 CH 3
H O
CH 3
Ph O
CH,
during esterification reaction only - COOH and - OH participates. There is no effect on structure of
configuration of carbon adjacent of these groups. So when () acid reacts with pure (+) alcohol two
esters are produced whine are diastereoisomers of each other.
CH,
Q.ll
P: C H 3 - C H 2 - 0 - C - C H 3
Q : CH 3 CH 2 OH
R: C H 3 - C - C H 3
O
when ethylene reacts with dil. H 2 S0 4 CH 3 CH 2 is produced during rate determining step, whereas P
gives resonance stabilized intermediate.
CH,
CH3-CH2-O-C-CH3
CH,
C H 3 ~ C H 2 - O = C~CH3
Classes
[36]
| BANSALCLASSES
TARGET IIT JEE 2007
ORGANIC CHEMISTRY
xni(XYZ)
AROMATIC
COMPOUNDS
CONTENTS
EXERCISE-I
EXERCISE - II
EXRECISE-III
EXRECISE-IV(A)
EXRECISE-IV(B)
ANSWER KEY
EXERCISE-I
Q. 1
(A) 2
Q.2
(B) 4
(C) 6
(D)8
(D) 14
Q. 3
Q. 4
Q.5
Q. 6
(D) C6H5N(C2H5)2
(D)HCB
Q.7
(C) 666
Q. 8
Q. 9
Which order is correct for the decreasing reactivity to ring monobromination ofthe following compounds:
(I)C6H5CH3
(II) C6H5COOH
(III)C6H6
(IV) C6H5NO2
(A) I > II > III > IV (B) I > III > II > IV (C) II > III > IV > I (D) III > I > II > IV
Q.10 Benzene on treatment with a mixture of conc. HN0 3 and conc.H2S04 at 90C gives:
(A) Nitrobenzene
(B) m-Dinitrobenzene (C) p-Dinitrobenzene (D) o-Dinitrobenzene
Q.ll
Which of the following structures correspond to the product expected, when excess of C6H6 reacts with
CH2C12 in presence of anhydrous A1C13:
(B)Q-CHC
L 2
to Bansal Classes
Aromatic Compounds
Page # 2
Q. 12
For preparing monoalky! benzene, acylation process is preferred than direct alkylation because
(A) In alkylation, a poisonous gas is evolved
(B) In alkylation. large amount ofheat is evolved
(C ) In alkylation, pollyalkylated product is formed
(D) Alkylation is very costly
Q.13
Benzene reacts with n-propyl chloride in the presence of anhydrous A1CL to give predominantly:
(A) n-Propylbenzene
(B) Isopropylbenzene
(C) 3-Propyl-1 -chlorobenzene
(D) No reaction
Q.14
In the sulphonation. acetylation andformylationofbenzene the group of effective electrophiles would be:
(A) SO:,CH 3 = O.HCO
(C) 5
(D)6
(D)5
Q.17
Q.18
Chlorinaton oftoluene in die presence oflight and heat followed by treatment with aqueous NaOI I gives:
(A) o-Cresol
(B)p-Cresol
(C) 2,4-Dihydroxytoluene
(D) Benzyl alcohol
Q.l 9
( A r ) r1 ^
N
CH 3
NO-,
r
NO,
CH 9 OM
NO2
"
S (C)V^
NO,
fr (D)
^
OoN
Q.20
In the reaction of p-chlorotoluene with KNH2 in liquid NH,, the major product is:
(A) o-Toluidine
(B)m-Toluidine
(C) p-Toluidine
(D) p-Chloroanilinc
Q.21
AICI3.A
(A) o-xylene
to Bansal
Classes
(B) p-xylcne
(C) both
Aromatic Compounds
(D) m-xylene
Page # 3
Q.22
C6H5CH3 C r 0 ^ >A
>B
The functional group present in B and name of the reaction would be
(A) -CHO, Gattermann aldehyde synthesis
(B) -CHO, Etard reaction
(C) -COCH3, Friedel Crafts reaction
(D) -CHO, Oxo reaction
Q.23
Which chloroderivative of benzene among the following would undergo-hydrolysis most readily with
aq.NaOH to furnish the corresponding hydroxy derivative.
.N02
(A)02N-/oV-C1
(
(B)02N-<O)-C1
NO2
(C) Me2N
CI
(D)(oyC\
Q.24 . The order of relative reactivity of the given halides towards SN2 reaction is:
(A) PhCH2Cl > PhCHClCH3 > PhCCl(CH3)2
(B) PhCH2Cl < PhCHCl(CH3) < PhCCl(CH3)2
(C)PhCHCl(CH3)>PhCH2Cl>PhCCl(CH3)2 .
(D) PhCHCl(CH3)>PhCCl(CH3)2 > PhCH2Cl
Q.25
An aromatic compound A' C7H6C12, gives AgCl on bonding with alcoholic AgN03 solution, and yields
C?H70C1 on treatment with sodium hydroxide. 'A' on oxidation gives a mono chlorobenzoic acid which
affords only one mononitro derivative. The compound A is:
CH,C1
(A)^
Q.26
(B)^C1
CH 2 CI
(D)(OlCH2CI
(C)[|rC1
Q.27
CH2CI
> ArBr
H2O
>ArH
> Ar ^ O V
0 H
>Ari
Which of the following substituted benzene derivatives would furnish three isomers in significant amount
when one more substituent is introduced:
CI
<A>fol
to Bansal Classes
Br
wlSC
<c>(ofBr <D>fo
Aromatic Compounds
Page # 4
Q.28
OCH3
knh
2 >
liq.NH,
C1
(C)'
V
>
(D) 1'If
Jj + NaOH
300C
300 L
200 atm>
Q.29
Q.30
CI
(A) ( o f
CI
(B)
(O [ )
OCH3
Q.31
NaNH 2
O
Br
OCH,
(A) I O I
, elimination addition
(B)
, elimination addition
OCH,
OCH,
(C) O I
Q.32
, cine substitution
Chloral+ {Q^>-C1
(A) Lindane
Conc.H 2 SQ 4
(D) O
(B) DDT
C6H6 + A
.additionelimination
(C)Tefflon
(D) Ethaneperchlorate
(C)Benzal
(D)p-Tolyl
(C) CH3CONH2
(D)CH2(C1)C0NH2
Q. 3 5 When benzene is heated with acetic anhydride in the presence of anhydrous aluminium chloride at 80C,
the product formed is:
(A) Benzoic acid
(B) Benzophenone
(C)Acetophenone
(D) Ethyl phenyl ketone
to Bansal Classes
Aromatic Compounds
Page # 5
Q.36
CJL
6
CH C0C1
AlClj
HCl
(D)None
The species responsible for nitration and sulphonationby nitric acid conc. H 2 S0 4 andfirmingH 2 S0 4 are:
(A) N0 2 and S0 3
(D) N0 2 and S0 2
A1C1
Q. 3 8 (A)
Which
substitution:
C6Hof6the
+ + following
N0 2
reactions
C 6 H 5 N0is2 not
+ Han+ example
(B)of
Celectrophilic
3 > C 6 H 5 - CH3 + HCl
fiH5 + CH3C1
OH
uvlight
(C)C6H6 + Cl2
Q.39
> C6H6C16
AC3
{ ( J ) + CH2CH2CH2C1
' '
(D)C6H5OH + CO + HCl
> K>)
CH,
CH,
(A) < 0 ^ CH 2 CH-CH 3
(B) < O y
IC
~CH
CH
(C)
CH2CH2CH2CH3
Q.40
Q .41
If the mixture of the following four aromatic compounds on oxidation by strong oxidising agent gives:
CH3
C2Hs
(C) Nitrobenzene
CH2OH
(D) chlorobenzene
CHO
Methyl group attached to benzene can be oxidised to carboxyl group by reacting with:
(A)Fe 2 0,
(B)AgN0 3
(C)KMn0 4
(D) Cr0 3
CH=CH2
Q.43
Q.44
(O)
>B
Q .45 The reaction of benzene with CO and HCl in the presence of anhydrous A1C1, gives:
(A) Chlorobenzene
(B) Toluene
(C) Benzyl chloride
(D) Benzaldehyde
to Bansal Classes
Aromatic Compounds
Page # 6
Q.46
(D)7
ci
iRp.n?:ofrichioride Hydrolysis ) Y
X and Y respectively are:
(A) Benzene, Benzaldehyde
(B) Toluene, Benzaldehyde
(C) Toluene, Benzoic acid
(D) Benzene, Benzoic acid
Q. 4 8 Product obtained when benzoyl acetic acid is heated with soda-lime is:
Q.47
"X" 2 V
(a)<^0^- c o c h 3
Q.49
(b)(o^C00H
(0<0>CH3
(D)
Q. 5 0 The highest yield of m-product is possible by the electrophilic substitution of the following:
(A)C6H5CH3
(B) C6H5CH2COOC2H5
(C) C6H5CH(COOC2H5)2
(D) C6H5C(COOC2H5)3
Q-51
OJ
+ H2
^ ^
( A ) Q
Q. 5 2
>
(A).
high pressure
( B ) 0
( C ) 0
Which of the following is/are produced when a mixture of benzene vapour and oxygen is passed over
V 2 0 5 catalyst at 775 K?
(D) Maleic anhydride
(A) Oxalic acid
(B)Glyoxal
(C) Fumaric acid
(A) 2
Ois:
(B)4
(C)5
(D)6
(C)
(B)
to Bansal
"Cl,NaBH
(C)
Classes
Aromatic Compounds
Page # 7
Q.57
In a reaction of C6H5Y, the major product (>60%) is m-isomer, so the group Y is:
(A)-COOH
(B)-Cl
(C) -OH
(D)-NH 2
Q.5 8 Which of the following will undergo sulphonation at fastest rate ?
(Q
(B)
(A)
(A)
(D)
(C)
(D) p-Xylene
Q.63
lJ
(D)|
(A) [|
N(CH 3 ) 3
CH 2 CH 2 NME 3
CH 2 -NMe 3
(B)f|^l
(D)
(C)|
Q. 64
When sulphonilic acid (p-H2NC6H4S03H) is treated with excess of bromine, the product is:
(A) tribromo product
(B) dibromo product
(C) monobromo product
(D)tetrebromo product
Q. 6 5 Ring nitration ofdimethyl benzene results in the formation ofonly one nitro dimethyl benzene. The dimethyl
benzene is:
GH 3
(A)
Q.66
a s
CH,
.*>(%
(O i
CH2N02
CH,
NO,
OCH 3
Q.67
no
(B)
(A)
(C)V^
OCH 3
(D) No reaction
OCH 3
(A)^^-N02
CI
to Bansal Classes
NH,
(B)
NH,
NH,
NO,
(C)
Aromatic Compounds
-NO,
(D)
NO,
Page # 8
Q.68
An aromatic compound of molecular formula CgH4Br2 was nitrated when three isomers of formula
C6H3Br2N02 were obtained. The original compound is:
(A) o-dibromobenzene
(B) m-dibromobenzene
(C) p-dibromobenzene
(D) None of these
Q. 69
(A) |l
(B)
|MJ
<c)(!
H^Y
H'Y
Q.70
CH-,
CH,
(D)
(D)|
(C)
(B)(J
(A)
(D)5
Q. 72 Which of the following species is expected to have maximum enthalpy in an electrophilic aromatic
substitution reaction?
H+ E
(I)
(II)
(HI)
(IV)
(V)
Q. 7 3 For the electrophilic substitution reaction involving nitration, which of the following sequence regarding
the rate of reaction is true?
l x
-6ll6> ^6nU6> ^r
66
( Q
CfiHfi =
CfiD, =
C,Tfi
(D)
C6H6
<
C f i H f i >'
C6D6 <
C6T6
CfiDfi <
C,Tfi
Q. 74 For the electrophilic substitution reaction involving sulphonation, which ofthe following sequence regarding
the rate of reaction is true?
(A)
CFIHFI >
C,D, >
C,T,
(B)
(D)
C6H6
< k
CfiHfi >
C
k
CfiD
< k
<
C,Tfi
Q. 7 5 The order of relative reactivity of the given halides towards SN1 reaction is
(A) benzylchloride > p-methoxybenzylchloride > p-nitrobenzylchloride
(B) p-methoxybenzylchloride > benzylchloride > p-nitrobenzylchloride
(C) p-methoxybenzylchloride > p-nitrobenzylchloride > benzylchloride
(D) benzylchloride > p-nitrobenzylchloride > p-methoxybenzylchloride
to Bansal Classes
Aromatic Compounds
Page # 9
EXERCISE -II
Q.l
(a)
(B>
00
(c)
(D)
l!)
Q.2
Q,3
CH 2 OH
(A)[o]
Q.4
COCH3
(B)[o]
(Ofof
OH
< )(Oj
Q.5
NaOH H2, 0
[OJ
395QC
(A)gf0H
'
h so
i 4
Bp3 HF
'
Alc 3
' >
Product is:
(B)@t0H
W.Jf
^loT 0 1
Q.6
Which of the following reactions of benzene proves the presence of three carbon-carbon double bonds
in it:
(A) Formation of a triozonide
(B) Hydrogenation of benzene to cyclohexane
(C) Formation of C6H6C16 by addition of chlorine
(D) Formation ofnitrobenzene on heating benzene with a mixture ofconcentrated nitric acid and sulphuric
acid
Q.7
Q. 8
N02
^(0)
NMe 3
Oe
iQ(o)
to Bansal Classes
Aromatic Compounds
Page # 10
Q. 9
The reaction of replacement of a hydrogen atom in benzene by alkyl group can be brought about with the
following reagents :
(A) Alkyl chloride and A1C1,
(B)AlkeneandAlCl 3
(C)Alkanol and alkali
(D)Alkanol and acid
Q.10
Q.ll
Q. 12
Q.13
(A)
Q.14
NO,
(Q
(B)
(D)
CI
(B)CH 2 =CH-C1
(A)
(C)CH,CH 2 C1
Q.15
The good method for converting benzene into propyl benzene is:
(A) C 6 H 6 + CH3CH2CH2C1 + Anhyd. A1C13
(B) C 6 H 6 + CH 3 CH 2 COCI+Anhyd. A1C13 and then treatment with Zn/Hg/HCl
(C) C 6 H 6 + CH 3 CH 2 C0C1 + Anhyd. A1C13 and then treatment with H 2 Ni
(D)C6H6 + Anhyd. A1C13 + cyclopropane
Q.16
CI
NHCOCH,
(D)
Q.17
Bansal
Classes
(B) CC1,
(C) -CH=CH-COOH ( D ) - N = C
Aromatic
Compounds
Page
#11
Q.18
'
CH3
(B)[o1
SO3H
(C)(0)
COOH
(D)[oTOH
OH
Q.22 Amongst the following, the moderately activating group is
(A)NHR
(B)--NHC0CH 3
(C)NR2
Q.23
(A)
(B)
(C)
(D)
(D)CH3
?
I
Q.24 Of the species PhSH, PhSR, PhSR and Ph - S - OR the meta-substituted product is obtained from
H A
(A)PhSR
(B) PhSR
II
0
to Bansal Classes
(C) PhSR
H
0
Aromatic Compounds
(D) P h - S - O R
II
o
Page # 12
Q.25
Column B
CH,
(A)
FO
I+
IN C H
+ Ph,C
(B)
(C)
CR0
C 0 0 H
>?
7> v
[ O I + n-Pr Br + ZndL
>?
(P)
Tropylium ion
(Q)
Benzaldehyde
(R)
(S)
Cumene
CH 3
Column II
O-H
(A)
C 0 2 t is evolved from
CP).
(B)
(Q)
NO 2
H-N-ME
(C)
(R)
(S)
N(^O^)
to Bansal Classes
Aromatic Compounds
Page # 13
Q.27
Column II
n>\
(P)
o
o
11
11
PhC^TT ^C-
(Q)
(C)
TMoTS] _
(R)
Ph-CH2-C-CH2CH3
(S)
(D)
Q.28
Column II
(P)
(B)
(Q)
(D)
to Bansal
Strongest Base
Classes
..(S)
Aromatic
Compounds
Page #14
EXERCISE-III
Q. 1
(i)
f^YN2
L j l
+C6H5CH2SK
|
CH,
>A
NO
(ii)
HzNNH2
T
N02
CI NH 2
CF,
V
> B
(iv)
(i)HN03.H2S04 ) D
(ii)NaOCH3 ,CH3OH
triethylene
GY
' COL
(ii)CuBr
CI
(y)
/
V
OCH3
3
(i)NBS,Benzoyl peroxide,CC14,heat ^ p
(ii)NaSCH,
CH,
JLNO 2
(vi)
L j i
CI
+CH3CH2ONa
N0 2
>G
(vii) f | T
N 0 2
+ C6H5CH2SNa
>H
NO2
Q. 2
Write the most stable resonance structure for the cyclohexadienyl anion formed by reaction of methoxide
ion with o-fluoronitrobenzene.
Q.3
Q.4
Offer an explanation for the observation that 4-chloropyridine is more reaction toward nucleophiles than
3-chloropyridine.
Q.5
Q. 6
Two isomeric phenols are obtained in comparable amounts on hydrolysis of p-iodotoluene with 1 M
sodium hydroxide at 300C. Suggest reasonable structures for these two products.
Q. 7
Given the structure ofthe cycloaddition product formed when benzyne is generated in the presence of furan.
^Bansal Classes
Aromatic Compounds
heat
Page #15
Q.8
In each ofthe following reactions, an amine or a lithium amide derivative reacts with an aryl halide. Give
the structure of the expected product and specify the mechanism by which it is formed.
Br
X
Br
Br
tjo
Q.9
Q.10
(a)
C.H.Br
+ CHL7(COOCHXH
3 )Z7
6 3
1
(i)ExcessNaNH
2>NH2
(ii)H20
CH 2 CH,CH,GH 2 COCH 2 CH 3
(i)ExcessNaNH2,NH3
(ii)H20
C1
CH 3
NCH 2 CH 2 NHCH 3
(c)
L j J
NaNH2
^ T r
>
ether
"
COOCH 2 CH 3
CH 3
^
f ^ j
CI
CH 3
F
(d)
> CfiH5CH(COOCH2CH3)2
F x J^OCH 2 CH 2 OH
T
i]
F
w
>
iT
heat
F
Aromatic Compounds
Page #16
EXERCISE - IV(A)
Q.l
Q. 2
Aiyl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halide due to
(A) The formation of less stable carbonium ion (B) Resonance stabilization
(C) Longer carbon-halogen bond
(D) The inductive effect
[JEE 1990]
Q.3
Q.4
Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH
gives:
(A)o-cresol
(B)p-cresol
(C) 2,4-dihydroxytoluene
(D) Benzoic acid
[JEE 1990]
Q.5
When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is
m-bromonitrobenzene. Statements which are related obtain the m-isomer are:
[JEE 1992]
(A) The electron density on meta carbon is more than on ortho and para position.
+
(B) The intermediate carbonium ion formed after initial attack of Br attack the meta position is least
destabilized.
(C) Loss of aromaticity when Br+ attacks at the ortho and para positions and not at meta position
(D) Easier loss of H+ to region aromaticity form the meta position thanfromortho and para position.
Q.6
Choose the correct statementfromthe ones given below for two aniline in:
+
NH 3
[JEE 1990]
(D) p-nitro aniline
[JEE 1993]
NH 3
(I)
(II)
(A) II is not an acceptable canonical structure because carbonium ions are less stable than ammonium
ions
.
(B) II is not an acceptable canonical structure because it is non aromatic
(C) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons
(D) II is an acceptable canonical structure
Q.7
Q. 8
Q.9
Q.10 Nitrobenzene can be preparedfrombenzene by using a mixture of conc. HN0 3 and conc. H 2 S0 4 . In
the nitrating mixture HN0 3 acts as a:
[JEE 1997]
(A) Base
(B)Acid .
(C) Reducing agent
(D) Catalyst
Q.ll
to Bansal Classes
Aromatic Compounds
[JEE 1998]
Page # 17
Q.12
0 -
V /
[JEE 1998]
\ 5 /
(A)
O"
O"
Q.13
A solution of (+) -2-chloro-2-phenylethane in toluene racemises slowly n the presence of small amount
of SbCl5, due to the formation of:
[JEE 1999]
(A) Carbanion
(B)Carbene
(C) Free-radical
(D) Carbocation
Q.14
Toluene, when treated with Br2/Fe,. gives p-bromotoluene as the major product, because the CH3 group:
(A) is para directing
(B) is meta directing
[JEE 1999]
(C) activates the ring by hyperconjugation
(D) deactivates the ring
Q.15
Q. 16 Identify the correct order ofreactivity in electrophilic substitution reactions ofthe following compounds :
CI
CH,
CO u
(II) ft n
(CH3)2NH
Q.17 F
(III)[r
DMF
NO,
(IV) II
^ ^
[JEE 2002]
H3CX
(A)02N-^0/-nh
(B)
H2CX
(C)
h2C/
N
H3C
(D)
NH,
Q.18
Br
to Bansal
Classes
Aromatic Compounds
Page #18
Q. 19 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodium acetate?
[JEE 2005]
C0
(A)
(C) Ctt 3
^a
(B) CH
SO3 N a + CHjCOOH
s- O
(D) CH3
+ S0
3
COCH3 + NaOH
EXERCISE - IV (B)
Q.l
A1C1
[ O J + (CH3)2CH.CH2C1
(i) Br,,Heat,Light
3 >(A)
[JEE 1992]
Q-2
C H C
Q.3
An organic compound (A). CgH6 on treatment with dilute sulphuric acid containing mercuric sulphate
gives a compound (B), which can also be obtained from a reaction of benzene with an acid chloride in
the presence of anhydrous aluminium chloride. The compound (B), when treated with iodine in aqueous
KOH, yields (C) and a yellow compound (D). Identify (A), (B), (C) and (D) with justification. Show
how (B) is formed from (A) ?
[JEE 1994]
Q. 4
Toluene reacts with bromine in the presence of light to give benzyl bromine while in presence of FeBr3 it
gives p-bromotoluene. Give explanation for the above observations.
[JEE 1996]
Q.5
6 5 2H5
(ii)NaCN
>
[JEE 1994]
Q.6
C6H5CH2CHC1C6H5
alcoholicKOH.heat
Q.7
C6H5CH - CH2
(A)
(A) + (B)
[JEE 1998]
[JEE 1998]
[JEE 1998]
(ii)CH 3 I
Q. 8
Normally, benzene gives electrophilic substitution reaction rather than thus electrophilic addition reaction
although it has double bonds.
[JEE 2000]
Q.9 , How would you synthesis 4 methoxyphenol from bromobenzene in NOT more than five steps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme.
[JEE 2001]
Q.10Carry out following conversions in 3 or less steps.
COOH
f o l
to Bansal Classes
COOH
>
f o l
Aromatic Compounds
[JEE 2003]
Page # 19
Q.ll
A compound C9H702C1 exists in keto form A and enolic form B. Enolic form B predominates at
equilibrium. On oxidation with KMn0 4 1 gives m-chlorobenzoic acid gives structures ofA and B.
[JEE 2003]
Q. 12 7-bromo-l, 3,5-cycloheptatriene is ionic compound, whereas 5-bromo-l,3-cyclopentadiene can't ionise
[JEE 2004]
even n the presence ofAg, Explain why?
Q.13
Give reasons:
H,C
(a)
(i)|j
[JEE 2005]
-Br
T \
c2HsOH(ag.)
: I I j
>
acidic solution
ch
3
(ii) B r - { j K __
C2HsOH(aq.) ) neutral
CH,
(b)
(i)02N^S^
CH,
(ii) H3C
NaOH(aq.)
p is not liberated
CH2N02
N
(C)
(i)
.0
-O
Conc.HNO
Conc" H 2 S O 4
/^/
N 0
r
^
NO2
Aromatic Compounds
ffi
, D(Explosive product)
[JEE 2005]
Page #20
ANSWER
EXERCISE
Q.l
Q.8
Q.15
Q.22
Q.29
Q.36
Q.43
Q.50
Q.57
Q.64
Q.71
KEY
-1
C
D
B
B
D
B
D
D
A
A
B
Q.2
Q.9
Q.16
Q.23
Q.30
Q.37
Q.44
Q.51
Q.58
Q.65
Q.72
Q.l
Q.5
Q.9
Q.13
Q.17
Q.21
Q.25
Q.27
A,B,D
Q.2
A,C
Q.3
A,B
Q.6
A,B,C
Q.7
A,B,D
Q.ll
Q.10 B
A
Q.14 C,D
Q.15
C
Q.18 A.
Q.19
B,C,D
Q.22 B
Q.23
(A) Q, (B) P, (C) R, S, (D) R
(A) P,Q,R,S, (B) Q, (C) P,Q,R,S, (D) p
C
B
D
A
B
B
A
A
B
C
A
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.52
Q.59
Q.66
Q.73
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
Q.53
Q.60
Q.67
Q.74
C
B
B
A
A
C
D
D
B
B
C
D
D
D
A
B
D
C
C
D
B
A
Q.5
Q.12
Q.19
Q.26
Q.3 3
Q.40
Q.47
Q.54
Q.61
Q.6 8
Q.75
EXERCISE-
A
C
A
B
C
B
C
D
A
B
B
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
Q.55
Q.62
Q.69
D
B
B
C
B
C
A
B
D
B
Q.7
Q.14
Q.21
Q.28
Q 35
Q.42
Q.49
Q.56
Q.63
Q.70
D
B
D
A
C
C
A
D
A
D
II
A,B
Q.4
A,B,C,D
Q.8
C
A,B,C
A,B
Q.12 A,B
B,D
Q.16 C
Q.20 A,B,C
A,B,C
B,C,D
Q.24 C,D
Q.26 (A) Q, (B) P,R,S, (C) R,S, (D) P,Q,R,S
Q.28 (A) R, (B) S, R, (C) P, (D) S
EXERCISE-III
C6H5CH?S
Q.l
H,NNH
NO,
(i)
(ii)
CI
Br
N'
OCH3
(iii)
0,N
NO 2
OCH,
OCH 2 CH 3
.NO 2
SCH 2 C 6 H 5
NO,
(vi)
(V)
CH,SCH,
(viii)
NO,
F 0CH 3/ 0~
Br
Q.2
OCH 2 CH 3
J \ .Br
Q.3
NO,
Q.4
Nitrogen bears a portion of the negative charge in the anionic intermediate formed in the nucleophilic
addition step in 4-chloropyridine, but not in 3-chloropyridine.
Y
ci
11
11
Compounds
Page
#21
Q.5
A benzene intermediate is impossible because neither on the carbons ortho to the intended leaving group
bears a proton.
Q.6
Q.l
Q.8
Q.15
D
C
D
Q.2
Q.9
Q.16
B
C
C
Q.3
Q.10
Q.17
EXERCISE - IV(A)
Q.4
D
Q.5
Q.ll A,C
Q.12
Q.18 D
Q.19
A
A
B
A,B
C
C
Q.7
Q.6
Q.13
C
D
no
Q.7
Q.14
D
A,C
EXERCISE - IV (B)
C(CH3)3
Q.l
[ O
CH7CH
Q-2
f O
Br?
A,hy
CHBrCH,
CHCNCH,
"MO
NaCN
o^
2-phenylpropane niitrile
COCH,
C=CH
Q.3
COOK
(B)(0)
(A)[0
(C)(0)
+
Q.4
In presence of FeBr3, Br 2 produces Br (an electrophile) which attacks the benzene ring at o-,p-position
to give p-bromotoluene. In presence of light, side chain is attacked to produce benzyl bromide .
Q.5
(a)
H-,0
(i) C 6 H 5 C H ( O H ) C = C H C 6 H 5 C H - C = C H -H-,0
OHJ
C 6 H 5 CH=CHCHO
=^C6H5CH=C=CH
C 6 H 5 CH=C=CH
OH
CFIH,
COOH
fO]
CHOCH
(")fO
Q.6
Sodalime
CHXCH
> [O
KCN
hv
C 6 H 5 CH 2 CH 2 CHC1C 6 H 5
K0H (ALC)
A
CN
CHCH3
fo]
COOH
CHCH3
-^[o
CH=CH,
Q.7
[ O
Br-,
,CHBrCH2Br
->fO
NaNH2 3 eq.
[ Q
C=CNa
CH,I
C=C-CH,
Aromatic
Compounds
Page
#22
Q.8
Benzene has resonance stabilization due to delocalisationofTc-electrons. Also during electrophilic addition
reactions, it loses its aromaticity. In electrophilic substitution reaction aromaticity is retained.
Br
Q.9
ONa
OMe
OMe
NaOH
[O
NaOH
conc.H 0 SO
AhighPr essure
SO.H
OMe
OMe
H,0
ONa
OH
Alternative rout
Br
Br
conc.H-SO,,
Br
Br
Na0H
->IQ
SO.H
JO
Me2S04
i O ]
^
ONa
OMe
OMe
Na0H
)[o
H,cr
A high Pressure
ONa
OMe
OH
COOH
COOH
COOH
conc.H 1 SO / 1
Q.10
(O)
HBF./KHE,
SO.H
OH
C=CH-CHO
C-CH 2 -CHO
Q.ll
* o
^
(A)
. . ( B ) .
Keto
Enol
Enol form is more stable due to extended conjugation
O
n
C-OH
(A)
Q.12
KMnO
CI
On ionization 7-bromo-1,3,4-cycloheptatriene gives tropolium ion which is aromatic with 671 electrons.
Br
()
+ Br
5-bromo-1,3-cyclopentadiene can't ionise as it will in that case give highly unstable antiaromatic cation
with 4 71 electrons.
Br
-X-
Br
Aromatic
Compounds
Page #23
CH3
Q.13 (a) (i) H5C6 - C - OC2H5 + HBr(acid); (ii) no reaction due to partial double bond character
I-
CH
(b) (i)
CH3
(c) (i) due to presence of lone pair of nitrogen atom NO group is electron denating and ortho, para
directing
(ii) N0 2 group is electron withdrawing and meta directing
(d) Due to reduction of central ring, three four membered antiaromatic rings become stable while on
recuction of terminal ring only one antiaromatic ring can be stabilized.
CH 3
t^J
NO,
to Bansal Classes
Aromatic Compounds
Page # 24
I BANSALCLASSES
^
ORGANIC CHEMISTRY
XII (ALL)
CARBONYL COMPOUND
CONTENTS
EXERCISE 1(A)
EXERCISE 1(B)
EXERCISE II
EXER CI SE III
EXERCISE IV (A)
EXER CISEIV (B)
ANSWER KEY
EXERC1SE-UA)
Q. 1
Q.2
OH
CH3-CHC-CH3
(a) + (b)
CH3
(a) and (b) respectively be:
(A) CH3CHO and CH3CHO
(C) CH3COCH3 and CH3COCH3
Q.3
Q. 4
Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reaction:
(I) Acid chloride
(II) Aldehyde
(III) Ketone
(IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C)III>II>I>IV
(D) I > IV > II > III
Q.5
Acetalorketalis:
(A) Vic dialkoxy compound
(C) a-alkoxy alcohol
Q.6
(B ) a, o-dialkoxy compound
(D) Gem dialkoxy compound
O
CHd3 -CH 2? -C-CH 2 COOC
7Hs
2
W >(A)
(i)LiA1H
4 )
(ii)H20/H
o
[X] will be:
CH 2 -OH
(B)IH
(A) HCHO
CH 2 -OH
<C4H,-OH+
fa Bansal Classes
OH
(D)HCN
Carbonyl Compound
[21]
Q.7
II
O
Q.8
Q.9
NH2OH/H
[X]
O
II
o
II
O
(A)[
Q.ll
O
1
(B)[
0
|
(C)^ Y
(D)" 3 '
Which one of the following compounds will give dimethyl glyoxal with Se02:
(A) Acetone
(B) Acetophenone
(C) Ethyl methyl ketone (D) Propanaldehyde
O
( ^ J C H 3 -J5a-> [X]
[X] will be:
ft
" U
Q.13
O
C H
- C - C H
O
3
c o o o h
> C H
- C -
O -
C H
[21]
Q.14
Q.15
(C) N a / H g / H ^
NaOH
5C
"
CH3
(X) and (Y) will respectively be:
(A) CH 3 -CH 2 -CHO and CH 3 -CH 2 -CHO
OH
C6HsCHO + CH3-CHO
will be
(A) One
Q.18
CH,
(B) Three
(C)Two
(D)Four
In the reaction:
/\ _~_ yy
+ wr
5h/a
" w
> [X]
[X] will be
OH
(A)f
Q.19
OH
(B)[
(!Bansal
Classes
OH
OH
i (c)[
O
i
( D ) ( ^
Carbonyl Compound
ISJ
Q 20
[X]
will be:
(A) C 6 H 5 -CH =CH-COOH
(B) N O 2 - < o ) - C H = C H - C O O H
(C) C 6 H 5 -CH=C-COOH
(D) N 0 2 - { o ) - CH = C - G O O H
c6H5
*no2
Q.21
> C 6 H 5 - CH - CH 2 - COOC 2 H 5
(ii)HOH/NH4Ci
(D)
b^CH-COOC2H5
is known as:
(A) Perkin reaction
(C) Reformatsky reaction
Q.23
CH 2 OH
Q. 24
Q.25
Metaformaldehyde is:
(A) Dimmer of HCHO
(B) Trimer of formaldehyde
(C) Tetramer of formaldehyde
(D) Polymer in which number of HCHO unit is more than 100
(!Bansal Classes
Carbonyl
Compound
ISJ
Q.26
[X]
Distillation
(B) Phorone
(D) 2-Butyne
Q.28
Q.29
Q.30
Q.31
(D)RCOOR
__hv/ci2
> (X)
aio.KOH/A
(B) 2-Hexanone
>(Y)
(C) 3-Hexanone
OH
(Z)
(D) Hexanedial
O
Aluminium tertiary butoxide
j)
Acetone
is knows as:
(A) Kolbe reaction
CO BH 3
t
ii)H202/0H
(Y)
(X) and (Y) are :
(!Bansal
Classes
Carbonyl Compound
ISJ
(D) CH3-CH2-CHO
KHS(
V A > ( X ) _JC2H5O)3M
)(Y)
O
II
(A) an aldol
TT^TI
CHUrl
(B) an acetal
O LHU
(C)aketal
(D)ahemiacetal
fa Bansal Classes
Carbonyl Compound
[21]
Q. 41 Questions given below consist oftwo statements each printed as Assertion (A) and Reason (R); while
answering these questions you are required to choose any one of the following four responses:
(A) if both (A) and (R) are true and (R) is the correct explanation of (A)
(B) if both (A) and (R) are true but (R) is not correct explanation of (A)
(C) if (A) is true but (R) is false
(D) if (A) is false and (R) is true
Assertion:
Benzaldehyde with HCN gives two isomeric compounds
Reason:
Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl group.
Q. 42 When D-glucose is treated with Br, water then the product is:
C02H
C02H
OH
HO
OH
(B)
OH
(Q
OH
OH
HOOH
HO-
HO
OH
(A)
CO 2 H
OH
OH
OH
OH
(D)
OH
OH
CO?H
OH
OH
OH
OH
[(CH^CQ] 3 A1
Q.43
A is:
OH
(A)
(B)
(Q
(D)
CH=CH-CHO
LlA1H4
fa Bansal Classes
p r o d u c t is
(B) ||^j-CH=CHCH 2 OH
(D) j ^ ^ C H 2 C H 2 C H 2 O H
Carbonyl Compound
[21]
The first step in a sequence involved treating ethyl trifluoroacetate with NH 3 to give a compound A. A on
treatment with reagent 'X' (alongwith gentle heating) produces a compound B (which on hydrolysis can
produce an acid). B on treatment with an orango metallic, 'Y', followed by hyydrolysis produces C.
Based on above passing attempt the following questions:
Q.45
J!
c
(A)
IIc
^OCH2CH?
(B)H 2 N-^ ^ C F 3
CF 3 ^ c ^OCH 2 CH 3
I!
(C) C F ^ ^ O C H . C H ,
NH
NH,
Q 46
Structure of B would be
Q.47
Q. 48
(A) CF, - C - N H 2
(B) CF 3 -C=N
(C) C F 3 - C H 2 - C N
(D) C F 3 - C H 2 - N H 2
'X' should be
(A) B a 0 2
(B)H202
(C)P4O10
(D)N20
(B) ( C H 3 ) 3 C - C - OCF 3
(C) CF3 - C - OH
O
rSH
-SH
Q.49
RaneyNi
CF3
\ /
(A)
CF3
\ /
(B)
OH
CF 3
\ /
(C)
(CH 3 ) 3 C
/
(CH3)3C
<!%Bansal Classes
E : 'E' is
/ X
(CH3)3C
,
S
(D)CF3-C-S-C(CH3)3
H
Carbonyl Compound
[9]
faiBansal Classes
Carbonyl Compound
[10]
EXERCISE-KB)
Q 1
(A) C H 3 - C - C H 3
(B)CH3-CH2-C-CH3
o
II
(C) Ph - C - CH 3
O
II
(D) CH3 - C 6 H 4 - C - CH 2 Ph
(P)
Q.2
C H - C2H5
- i
i ) 0
>
(B) CH 3 -CH=CH 2
CO/H2/CO2(CO)S__>
(II)H,0
CH 3
(C) C H
Q. 3
CH,
- C = C H - M ^
(D)
NaOH,H202
CH3-C.CH
(D)Allyl alcohol
Q.4
Q. 5
11
O
II C 2 H 5 andCH 3 MgBr
C-
(!Bansal
Classes
Q.7
II
o
NH2OH/Ha > pq
[Y]
O
II
O
II
(A) C 6 H 5 -C-NHCH 3
(B) C H 3 - C - N H - C 6 H 5
Q.8
Q.9
(D) C6H5CH2CN
(D) CH3CO
0
Q.10 Which one ofthe following compounds will not give aldol:
(A)Acetaldehyde
(B) Formaldehyde
(C) Pivaldehyde
(D) Crotonaldehyde
Q. 11 Knoevengcl reaction is catalysed by :
(A)NaOH
(B)NH3
(C)EtOk
(D) Pyridine
(D) Dimerization
Q. 13 Which one of the following reagent(s) is/are used for the conversion ofketone into hydrocarbons?
(A)LAH
(B)N2H4/H202
(C) Mg Hg F^O
(D) NaHgHCl
Q. 14 Schiffs reagent gives pink colour with:
(A)Acetaldehyde
(B) Formic acid
(B)Ql0I1
OCH3
fa Bansal Classes
(D)CH
(D)
CH33-CH
-CH
^OCH,
Carbonyl Compound
[21]
ci & CH3CHO
(A)
(C) 0 <
Q.17
& HCHO
C H 3
(D) c i X ^ X X ^ .
O
II
0
II
(A) Ph - C - Ph
(B) HO - (CH 2 ) 3 - C - CH 3
O
II
(C) CH 2 OH - C - (CHOH) 3 - CH 2 - OH
Q.18
CH3CHO
&
O
II
(D) HO - CH 2 - ( C H 2 ) 4 - C - CH 3
O
II
(A)
CH^z = CH - C - H
V 1
(i)NaCN
U)
(ii)H 2 0
>
(B) CH,Z = C H - C - H
H 2 O/H
(C)|>
+ CH2(COOMe)2
>
o
o
(D) I
o
'
CH CH CN
Base
U-CH-CN
6 r
Q. 19
Q.20
Mixture of Ph-CHO & HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation ofHCHO
(B) Reduction ofHCHO
(C) Oxidation of Ph-CHO
(D) Reduction of Ph-CHO
Q.21
faBansal Classes
Carbonyl Compound
[13]
(a)
Q. 23
COQH
OH
mO
SOjH
(c)u
cd)
Asparmate, an artificial sweetener is a peptide and has the following structure. Which ofthe following is
correct about the molecule?
7A
h 2 N^ ^ ^ N N H
CH,
(A) It has four functional groups
(B) It has three functional groups
(C) on hydrolysis it produces only one amino acid
(D) on hydrolysis it produces a mixture of amino acids
Q. 24 Match List-I with List-II and select the correct answer using the codes given below the lists.
List-I (Compound)
List-II (Used as)
(A)
1,4 addition
(P)
O
II
P h - C H 2 - C - C H = CH2
(B)
Tautomerism
(Q)
PCC
O
(C)
Allylic bromination
(R)
(D)
(S)
NBS
Q. 25 Match list-1 with list-11 and select the correct answer using the codes give below the lists:
List-I
List-II
(A)
CH 2 CH-CHO -
(B)
KaB 4
(P)
Acetal
(Q)
Setoffs base
(C)
C6H5COCH3+CH3-CH2-NH2 i t - *
(R)
Unsaturated alcohol
(D)
(S)
Enamine
(!Bansal Classes
"
>
Carbonyl Compound
ISJ
Q. 26
Match list-I with list-II and select the correct answer using the codes give below the lists:
List-I
List-II
(A) C 6 H 5 CHO + HCHO
(B) C 6 H 5 -H+CH 3 COCI
(C) C 6 H 6 +CO+HCI
0H
> C 6 H 5 CH 2 OH + HCO O
ANHY ALC 3
ANHY ZNC 2
Cu.,CL
'
OH
(O)
'
> C 6 H 5 -CO-CH 3
(P) Cannizzaroreaction
(Q) Friedel Crafts reaction
(R) Reimer-Tiemann reaction
(!Bansal Classes
' -
)[qJ"CH0
Carbonyl
Compound
ISJ
Q. 3 (b) Equilibrium constants for the dissociation (Kdiss) of cyanohydrins according to the equation
OH
I
I
Kdiss
RCR'
II
RCR' + HCN
CN
Cyanohydrin
Aldehyde
Hydrogen
or ketone
cyanide
have been measured for a number of cyanohydrins. Which cyanohydrin in each of the following pairs has
the greater dissociation constant ?
OH
OH
(i)
CH3CH2CHCN
(ii)
, HCCHCN
,
M OH
C
FI
Q. 4
or
(CH3)2CCN
H
Cfi6H<CCN
5 ?
<
CH,
Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give aldehydes.
Propose mechanisms for the two steps in this synthesis.
O-CH 2 CH 3
O-CH 2 CH 3
H-C-0-CH2CH3 +R-Mg-X
>R-C-0-CH2CH3
O-CH 2 CH 3
acetal
J}
aldehyde
Q. 6
PV
ethyl orthoformate
Q. 5
H3O+ >
NaQCH3
||
(CH3)3CCCH2OCH3
CH3OH
(88%)
O
(a)
CH3-C-CH3+HO-CH2-CH2-NH2
"2M >
.CH 2 - CH 2 - CH 7 -NII 2
w
Q o
"
o
(C)
C - CH3 - COCb/NeOH/HDH
\
fa Bansal Classes
(ii) H
Carbonyl Compound
[21]
Q.7
A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest reagents
appropriate for each step in the synthesis.
0
OH
54%
(CH3)3CCCH3)3CCCH2Br
Q. 8
>(CH3)3 CC>"cH2
H
Show how you would accomplish the following syntheses efficiently and in good yield. You may use any
necessary reagents.
O
(a)\
0
(b)
CH2OH
CHO
CHO
CHCH2CH3
CHO
(,!
^
CHO
Q. 9
0
68%
>(CH3)3CCHCH2Br
CHO
c r f - + c r i ?
r - r r r
O
CH2CH2CH2CH2Br
KOC ( CH 3 ) 3
benzene
(76%)
Q. 10 IdentifyAtoD:
Me2CH - CH2 - CHO
Q. 11
> (A)
HNO 2
>
(B)
>
H2O/H+/A
(G)
>
(D)
HCN/OHS
> ( A )
H20/HS/A_^(B)
H2S04
(i)BH 3 /THF
> ( c )
>
(ii) CH3COOH
(i) BH3/THF I
(ii) H2O2/OH I
(D)
Q. 12 Give the structure of the substance for each of the following reaction:
O
11
yO
(a)
(X)
NaOH/A
>
c-
(b)
(Y)
NaOH/A
>
CH 3
\\
CH
(!Bansal Classes
Carbonyl Compound
ISJ
(C)
(Z)
o
Q.13
Each of the following reactions has been reported in the chemical literature. Write the structure of the
product (s) formed in each case.
(a)
(b)
CI
Q.14
IdentifyAtoE:
CH^x/^O
LSH
H 2 /Pt
<fy
Conc, H 2 S 0 4 / A
*
0 )
(C)
Q.15
^ A )
CF3COOOH
TR)
H2Q
>
(C)
NH3/A
)(
T>)
(i)BH3/THF
(p )
(ii) H 2 0 / H
Q. 16
CI
I ^ S
_ D M S O ^
.(B)
( A )
l ^ J
Q.17
(a)
(B)
(C)
BA0
'",,A
' ( D ) ^ F ^ ( E )
K O H / A
(ii)HOH
Syntheses of each of the following compounds have been reported in the chemical literature. Using the
indicated starting material and any necessary organic or inorganic reagents, describe short sequence of
reactions that would be appropriate for each transformation.
1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanone
H X
/ A
J FROM C 6 H 5 C
CH3 CH2
(c)
u
(!Bansal
Classes
Carbonyl
Compound
ISJ
EXERCISE-III
Q. 1
Compound (A) C9H, 0O is inert to Br2 / CC14 and on vigrous oxidation with hot alkaline KMn04 yields
benzoic acid. (A) gives red precipitate with 2,4 DNP / HC1 / A.
(a) Write all possible structures of [A] and
(b) How can these isomers be distinguished by chemical tests?
Q.2
Compound (A) C8HgO is water insoluble and gives yellow precipitate with I2/NaOH. It reacts with NH^OH
in the presence of NH4C1 /NH4OH to give two geometrical isomers (B) and (C) having MF CgHgON.
These two compounds do not undergo dehydration. What will be structures of (A), (B) and (C) ?
Q. 3
A dithiane synthesis can convert an aldehyde to a ketone. The aldehyde isfirstconverted to its dithiane
derivative, which is deprotonated and alkylated. A mercuric chloride - assisted hydrolysis gives the
ketone. Show how this techinque might be used to convert benzaldehyde to benzyl phenyl ketone
Q.4
Wolff-Kishner reduction (hydrazine, KOH, ethylene glycol, 130C) of the compound shown gave
compound A. Treatment of compound A with m-chloroperoxybenzoic acid gave compound B, which
on reduction with lithium aluminium hydride gave compound C. Oxidation of compound C with chromic
acid gave compound D (C9HI40). Identify compounds A through Din this sequence.
Q. 5
Q.6
The sex attractant of the female winter moth has been identified as the tetraene
CH3(CH2)8CH=CHCH2CH=CHCH2CH=CHCH-CH2. Devise a synthesis of this material from
3,6-hexadecadien-l-ol and allyl alcohol.
Q. 7
Hydrolysis of a compound A in dilute aqueous hydrochloric acid gave (along with methonal) a compound
B, mp 164-165C. Compound B had the molecular formula C )6 H I6 0 4 . Whatistheresonable structure
for compound B?
CO-
/^-CHCH(0CH3)2
OH
Compound A
Q. 8
Q. 9
Compound (A) C5Hg, decolourises bromine water and on reduction with H2/Pt gives compound (B)
having MF C5H!2. A gives compound (C) with I V Lindlars catalyst and compound (D) with Na/NH3
(/). Compound (C) and (D) are isomers having MF C5HK). (A) on hydration gives two isomeric
compounds (E) and (F) having MF C5H10O. (E) gives yellow precipitate with 12 / NaOH but (F) does
not. What will be the structures of (A) to (F) ?
Q. 10 An organic compound (A) contains 40% carbon and 6.7% hydrogen. Its vapour density is 15. On
reacting with a concentrated solution of potassium hydroxide, it gives two compounds (B) and (C).
When (B) is oxidised, original compound (A) is obtained. When (C) is treated with concentrated HC1,
it gives a compound (D) which reduces Fehling and ammonical AgN0 3 solution and also gives
effervescences with sodium bicarbonate solution. Write structures of (A), (B), (C) and (D) and explain
reaction.
tBansal
Clt
Carbonyl Compound
EXERCISE-IV (A)
Q. 1
Q.2
Q.3
[IIT 1991]
Q.4
[IIT 1992]
Q.5
An organic compound C 3 H 6 0 does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and
does not react with metallic sodium. It could be:
[ITT 1993]
(A) CH 3 CH 2 CH0
(B) CH3COCH3
(C) CH2=CH-CH2OH
(D)CH 2 =CH-0-CH 3
Q. 6
Under Wolif Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol
(B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol
(D) Benzophenone into Diphenylmethane
[IIT 1995]
Q.7
CH3 \
CH
(A)CH3COCHO
Q.8
[IIT1990]
[IIT 1995]
P + Se + I^O
(B)CH 3 COOCH 3
(C) CH 3 C0CH 2 0H
(D) None
[IIT 1996]
Q. 9
Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl
(B)MeCHO
(C) MeCOOMe
(D) MeCOOCOMe
[IIT 1997]
Q 10 In a Cannizzaro reaction the intermediate which is the best hydride donor is:
[IIT 1997]
H
O"
fa Bansal
Classes
Carbonyl Compound
[21]
Q. 11
CH3CHO + H 2 NOH
(A) pH = 1
Q. 12
Among the following compounds, which will react acetone to give a product containing > C = N (A)C 6 H 5 NH 2
(B)(CH 3 ) 3 N
(C) C 6 H 5 NHC 6 H s
(D) C 6 H s NHNH,
[IIT 1998]
The product obtained via oxymercuration (HgS0 4 -H 2 S0.) of 1 -butyne would be
Q. 13
[IIT 1997]
O
||
(A) CH 3 CH 2 - C - CH 3
(B) CH 3 CH 2 CH,CHO
[IIT 1998]
Q. 14
[IIT 1998]
(D) Trideutero acetaldehyde
Q 15
[IIT 1998]
(D) CICH2CH2CI
(C)CC14
Q 16
[IIT 1998]
Q 17
[IIT 1999]
OD
I
(A) C H , - C = CH 2
O
II
(B) CD 3 - C - CD 3
OH
OD
I
I
(C) CH 2 = C - CH 2 D (D) CD 2 = C - CD 3
Q. 18
Q. 19
/V
v
ch3
HO"
(A)Zn(Hg), HC1
J.
[IIT 2000]
(D) 2,3-hexandione
[IIT 2000]
C I L 2 C I 1 3
H 0
(B ) H H 2 NH 2 , OH
(C)H 2 /Ni
(D) NaBH4
Q.20
A mixture of benzaldehyde and formaldehyde onheating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate
(B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate
(D) benzyl alcohol and methyl alcohol [ IIT 2001 ]
Q.21
(B) CH , - C = NNHCONH,
i
CH 3
(C) C H 3 - C = NCONHNH 2
(D) CH 3 CH 2 CH-NC0NHNH 2
CH,
(!Bansal Classes
Carbonyl
Compound
[IIT2002]
ISJ
/CHO
Q.22
' Q
OHCN
(i)NaOH(excess)100C
[IIT 2003]
(ii)H+/H20
s
OHC /
CHO
HOOCv
COOH
HOOC
(A)
CH 2 OH
(C)
COOH
OX
COOH
CH 2 OH
OCOCH3
Q.23
^OCOCH,
Acidic
(A) 2, 4 DNP
(C) NaHS0 3
Q. 24
The order of reactivity of phenyl Magnesium Bromide with the following compounds is [IIT 2004]
C H
H,C
(I)
(IT)
Q.25
What is X?
(A) CH3COOH
Ph
-COOH
+X
MeO
Ph
(Til)
'CHO
Q.26
[IIT 2003]
Hydrolysis
CH COONa
>
[IIT 2005]
MeO
(D) CHO-COOH
The smallest ketone and its next homologue are reacted withNt^OH to form oxime.
(A) Two different oximes are formed
(B) Three different oximes are formed
(C) Two oximes are optically active
(D) All oximes are optically active
[JEE 2006]
faBansal Classes
Carbonyl Compound
[23]
EXERCISE-IV (B)
Q. 1
Q2
C . H . O H and heat
C)kcn/h2s4
=Q
H
(d)
| ITT 1995]
[IIT 1996]
>D.
(ii)LiAlH4
Q. 3
Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures ofthe oximes.
[IIT 1997]
Q.4
An aldehyde (A)<CuHgO), which does not undergo self aldol condensation, gives benzaldehyde and
two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid. Identify
the compounds (A) and (B).
[IIT 1998]
Q.5
(a)
[IIT 1998]
(ii)
(b)
Q. 6
Cf CH3
(CH3)2CHOCH3
HI(excess).heat
\J
J^xhc6H5
[IIT 1998]
(A) + (B)
^)LiAlH
Q.7
Q. 8
(C)
[IIT 1998]
(ii)H+,heat
[IIT 2000]
^Ph
Q. 9
[IIT 2000]
0
-> A + B
L f C (C 7 H ] 2 0)
Q. 10
(i)
(ii)
(iii)
(iv)
faBansal
Classes
Carbonyl
Compound
[24]
[IIT 2002]
r A
^^ ^
CH2CH2CH3
CH=CHCH.,CrNa +
Q.12
Cl2/FeCl3^A_NgL^B
^D-
HN0 3 / H 2 S 0^
H2/Pd/C
(C)
I Ale. KOH ^ ^
ozonolysis ^ ^
ozonoi sis
(A)
y (F) + (G) NaOH ) HCOONa + 1 alcohol
(D) is isomer A. E gives negative test with Fehling solution but gives iodoform test. F and G gives Tolleris
test but do not give iodoform test. Identify Ato G
[IIT 2003]
Q. 13 An organic compound (P), C 5 H u ,0 reacts with dil. H 2 S0 4 to give (Q) and (R). Both (Q) and (R) give
positive iodoform test. The reactivity of organic compound (P) is 1015 times more than ethylene with
[IIT 2004]
respect to dil. H 2 S0 4 .
(i)
Identify the compounds (P), (Q) and (R).
(ii)
Give reason for the extraordinary reactivity of compound (P).
Q.14
-X
(i)O,
(ii) Zn / CHjCOOH
.Y NaOH
[IIT 2005]
Identify X and Y.
Q. 15 Which of the following disaccharide will not reduce Tollen1 s reagent?
CH2OH
(a)
CH2OH
9 /H H\ J
oho
(b)
CH2OH
OHJO H
K
HHCK
H
OH H
OH H
fa Bansal
Classes
[IIT 2005]
. HOH2C
OH H
OIOH
Xonm
H
OH
(P)
Carbonyl Compound
[21]
ANSWER
KEY
EXERCISE-I(A)
Q.l
Q.8
Q 15
Q.22
Q.29
Q.36
Q. 43
Q.50
C
A
B
C
A
B
B
B
Q.2
Q9
Q.16
Q.23
Q.30
Q.37
Q.44
B
B
B
A
D
D
C
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
C
B
C
C
D
D
B
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
A
C
D
B
A
C
B
Q.5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
D
B
C
C
C
D
C
B
A
D
D
D
C
A
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
Q.7
C
Q.14 A
Q..21 C
Q.28 C
Q.35 B
Q.42 A
Q.49 C
EXERCISE-KB)
Q.l
Q.5
Q9
Q.13
Q.17
Q.21
Q.24
Q.26
Q.l
C,D
Q.2
B,C
Q.3
Q.6
A,B,C,D
A,B,C
Q.7
Q.10 B,C
A,B,C,D
Q.ll
D
Q.14 A
Q 15
B,C,D
Q.18 A,C,D
Q.19
A,C,D
Q.22 A,B,D
Q.23
Q.25
(A) P, R, (B) P, (C) S, (D) Q,S
(A) P, (B) Q, (C) S, (D)R
EXERCISE-II
A,C,D
Q.4
A,B
Q.8
B,D
Q.12
Q.16
A,B,C
Q.20
A,B,C
A,D
(A) P, (B) Q,S, (C) S,
(b) C H ^ C H ^ O ^ - O H
(d) CH 3 - CH 2 - CH - CH 3
A,B
B,D
A
A,B
A,D
(D) P
OH
OH
OH
(e) CH3 - CH 2 - CH - C = CH
(f) CH 3 - CH 2 - CH - (CH) 4 - CH 3
(g) CH 3 - C H 2 - C H - O C H ,
OH
H
(i) CH 3 -CH 2 -CH-NH-PH
(j) CH 3 - CH 2 - CH - N - CH ,
CH 3
(k) C-C-C=N-OH
(m) CH 3 -CH 2 -CH 2
(o) semi carbazane
OH
(q) CH 3 - C H 2 - C H - C N
l&Bansal
Classes
Carbonyl Compound
[26]
o
Q.2
(a)
C-C-C-C-OH
(b) CH, - CH 2 - CH 2 - CH = C - CH 2 - CH ,
OH
(c) C - C - C - C = N - O H
CHO
(d) C - C - C - C - P h
OH
(e)
Ph - CH = C - CH 2 - CH 3
I
CHO
(0 C - C - C - C H - C = CH
(g)C-C-C-C < ]
(h) C - C - C - C
(i)
(j) Cyclohydrides
2alcohol
OH
(k)
2 alcohol
(1) CH 3 - C H 2 - C H 2 - C H - C H - C 0 2 E t
Et
OH
i
Q 3(b) (I) (CH 3 ) 2 CCN
(ii) C 6 H 5 CCN
CH 3
Q.4
R-Mg-X
Q.6
(a) C H 3 - C H - N H - C H 2 - C H 2 - O H
(b)
CH,
O
(c)CHCl3 + ^ ^ - C - O H
Q.7
HO/Br2
Q.8
H2 / N i ;
NaOH
CH2-OH
(b) (i) CH 2 - O H , (ii) NaBH 4 , (iii) H 3 0 + , (c) (i) CH 2 - O H , (ii) PH 3 P=CH-Et
CH2-OH
(d) (i) H 2 , (ii) Ni;
CH2-OH
(e) (i) H2s (ii) Pd-C ;
(f) NaBH 4
NH.
Q. 10
OH
(B) Me 2 CH - CH 2 - CH - CN
(A) Me 2 CH - C H . - C - CN
H
faBansal Classes
Carbonyl
Compound
[23]
OH
(C) M e X H - CH, - C H - C 0 2 H
OH
Q.ll
OH
(A) CH 3 - C - C H 3
(B)CH3-C-CH3
C-CH 3
CH,^
(a) (X) |
( C ) C H 3 - C = CH 2
CO2H
CN
Q.12
(D) Lactide
U CH,
CHO
CH22 -C=CH
3
1(
__/S-CH2-OH
(a) CH 3 -/
CO2H
fO
<b)
Y=c<PH
CH
Ph
- PH
cr
O
CO,H
Q.15
(A)
(B)
(C)
Q.16
(A)
(B)
(C)
M:O,H
CHJ-CHJ-CN
(D) f
>-C-C-C02H
CH2 CH2
CO2H
Q.17
(b)CH 3 MgBr/ H \ A
CH3
(0
+ H-C-C-C-C =C
L(0 M 8 i (iii) PCC
(u)H'
(iv) Ph 3 P=CH 3
EXERCISE-HI
Q.l
Possible structure an
(B ) Ph - CH - CH 3
CHO
faBansal Classes
Carbonyl
Compound
[23]
o
(C) P h - C - C H 2 - C H 2
(D) P h - C H 2 - C - C H 2
O
o
.2
Q.4
Ph - C - CH,
Ph-CH=CH-CH 2 -OH
(A)
(B)o:
(oH0Oo
(D)
Q.5
PIK
O-CH,
I "
0-CH-(CH2)5-CH3
c
H"
Q.7
PhCHCHOH
/
\
o
o
\
/
CH-CH
OH
Q.8
Ph
OH
I
CHI
CH 2
OCHoJ
I
CH
I
CH2
I
CHO
I
CH7-
CH 2
O
I
CH 2?
I
CL IO -
( a &(3)
Q.9
(A) C-C=C-C-C
(B) C - C - C - C - C
Q.10
(E) C - C - C - C - C (F) C - C - C - C - C
il
0
Empirical formula of (A) = 0 ^ 0 ;
Molecular formula of (A) = CFIjO
HCHO
CH 3 OH
HCOOK
HCOOH
Methanal (A)
(B)
(C)
(D)
EXERCISE-IV
Q.l
B
Q.8
B
Q. 15 B
Q.22 C
Q.2
Q.9
Q.16
Q.23
l&Bansal Classes
A
A
B,D
D
Q.3
Q.10
Q.17
Q.24
D
D
B
C
Q.4
Q.ll
Q.18
Q.25
B
B
B
C
(A)
Q.5
Q.12
Q.19
Q.26
Carbonyl Compound
D
A,D
B
B
Q.6
Q.13
Q.20
D
A
A
Q.7
A
Q. 14 A,B,D
Q.21 A
[29]
EXERCISE-IV
Q. 1
(B)
C6H5CH = CHCOOC2H5
(D)
CH3ch2x^
Q 2
/"
^OH
Cx
CH2NH2
(a racemic mixture)
Q3
C6H5-C-CH3
II
'
N-OH
s n
Y
and
C6HS-C-CH3
II
HO-N
anti (isomers)
CH=CH-OC-CHO
Q.4
[Ol
Ozonolysis
X )
>
fO f
COOH
C 0 0 H
COOH
(Oxalic acid)
(B)
Q.5
C 6 H 5 CH-C = CH
-H,0
OH^
C6H5CH=CHCHO v TautomerisatioiT C6HSCH=C= CH
C6H5CH=C= CH
OH
+
'CH,
C H
Q.6
1\
_
> H O C H 33
CH,/'
uv e ess),
HI
^ Af
C H
3\
> _ p C H L + CHgl
'CH,
CHC 6 H 5
Q.7
C f i HcCHO
ase
+Base
>
(C)
faBansal Classes
(D)
Carbonyl Compound
[23]
CH3
C-CH 3
Q.9
Br2+NaOH ^ f
(A)
(C)
(B)
CHO
Q.10
o
/CH3
"j^COONa + C H B r 3
(A) ( O )
or [ O ]
OCH3
o
Mott
CCH3
CH ? OH
CHO
( B ) [ 0 ]
CH 2 OH
( C ) ^
OH
COOH
O O f O l
CH 3
OH
0-CH=CH 2
^ l O
OH
NO,
NO,
Bu
Bu
Q.ll
(D)f c\v_
(C) c r y
(A)
C1
O-CH 2 -CH=CH 2
(E)
O-Pr
Q. 12
(A)
CI
CI
(B)
(C)
ale. K O H
(A)
Ozonolysis
HCHO + MejC-CHO
(F)
NaOH ^
(G)
H C O O N a + M e g C - C H j O H (lalcohol)
CH 3
Q.13
1 0
Ois
CH,
^
O R
H-
H 2 c <
/\
C H 3
CH 3
I
x+
H3C
0'
CH.
CH,
CH 3
H,0
)H3C"
"O
+ C2H5OH
Highly stable c a r b o c t a i o n
P is stabilized by r e s o n a n c e
^Bansal
Classes
Carbonyl Compound
[31]
(X)
Q . 15 In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why
Fehling solution cannot react with this.
In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce
Fehling solution.
fa Bansal Classes
Carbonyl Compound
[21]
I BANSALCLASSES
*
ORGANIC CHEMISTRY
XII (ALL)
EXERCISE
Q.l
-1(A)
Q.2
(B)R-C-O-
(C)R-C-
o
(D) R - C - N H -
C6HS-C-CH3
6
(B)C6H5COOH
(C) CgHj-CRjOH
(D)CH3COOH
CH 3 MgBr
) C H
+ ( A }
4
>CHBr3 + [X]
(ii)ir
( B
(ii)H20/H
Brz/A
RCOOAg
>R-Br
which one of the following acid will give maximum yield ofR-Br in the above reaction?
(A) CH3 - CH - COOH
CH3
CH3
(D) All will give same yield
(C) C H 3 - C - C O O H
CH3
Q. 5
Benzoic acid on treatment with hydrazoic acid in the presence of concentrated sulphuric acid gives:
(A) Benzamide
(B) Sodium benzoate (C) Aniline
(D) C6H5CON3
Q.6
C2H5
N,H/Conc.H,SO,
CH3-C-COOH
C3H7
MXJ
^-^CH3-C-NH2
C3H7
is called:
(A) Schmidt reaction
(C)Hofinann rearrangement
<fIBansal Classes
r l
Page # 2
Q.7
[ X ] will b e :
OH
[Y] will be:
(A) CH 3 -CH-C=0
(B) CH2=CH-COOH
OH
n
(D) CH3-CH
Q. 9
W
o
o
CH-CH3
Acetylation reaction with acetyl chloride is carried out in the presence of which solvent?
(A)HOH
(B)CH3OH
(C) Pyridine
(D) NaOH
O
C6H5 H
" St?
C H
6 5 ~C-CH2-C6H5
> Aspirin
(B) o-methoxybenzoic acid
(D) /?-Hydroxybenzoic acid
Bansal Classes
fi-0-CH2C6H5
(D) Cannizzaro reaction
Page #3
Q.13
O
c2H5QNa
C 2 H 5 OH
>
[X]
C-CH2-C-CH3
(A)
O
I!
HC = CH - C - CH,
(B)
H
o
(D) C H 3 - C - C H 2 - C O O H
(C) C H 3 - C - C H 2 - C - | ^ J '
Q.14
Q.15
Q.16
(B) Three
2h5HL
C 2 H 5 OH
(C) Two
(D) four
'CH3
L,MH4
)[X]
-CH3
(B)C6H5COOH
(C)C6H5CONH2
(D) C 6 H 5 -CH2-N:
-CH,
Q.17 Which one of the following compounds gives carboxylic acid with HN0 2 ?
O
(A)C6H5-C-C1
(B) C6H5CONH2
(C) C H 3 -0C - O - C
fl- C H 3
(D) CH3COOC2H5
fe Bansal Classes
Page #4
Q .18
H2 /Hffi
OH
> Product
OH
OH
(D) C H 3 - C H - C O N H 2
Q.19
Q.20
(l)NHs
> [X]
Imole
(ii)H20
(B) a-Aminoamide
(D) 3-Aminoamide
(ii)H20/H/A
(i)Zn
(ii ) N H 4 C l / H O H
(iii)HOH/H / A
X
(C) CH 2 - CH 2 - COOH
NaOH/HOH
< f I B a n s a l Classes
Page # 5
Q.22
COOH
O ]
[X] will be:
CI
(A)[OT
Q.23
OH
COOH
CI
C0Cl
(B)
>
(D)
CQC
(A)C 6 H 5 ONa
Q.24
-(C) L O J ^
)[pT
ONa
A.
(C)[pJ
ONa
A.
C00H
(D)(cTpC00Na
A^COOU
200 c
fQJ
[X] will be:
(A) Phenyl salicylate
Q.25
) [X]
(B) Aspirin
(C) Phenol
Arrange these esters in decreasing order of ease of esterfication with CH, OH/H:
(I) CH , - CH - COOH
i
CH,
(II) CH 3 - CH - CH 2 - COOH
I
CH 3
CH 3
(III) CH, - C - C O O H
(IV)(CH,-CH 2 ),C-COOH
CH 3
(A) 11 > 1 > III > IV
Q.26
(II) N O 2 - { O ) - C O C I
O
(NI)CH3-/R)YCOCI
(A) II > IV > I > III
<fIBansal Classes
(IV)OHC-\OVC-CI
(C) I > II > III > IV
amines
Page # 6
Q.27
(^Mn0 4 /8 H /A
(ii)H
(B) Eltylamine
VKOH
(ii)NH3/A
(C) Propylamine
(D)Acetamide
Q.29
Q. 3 0
(D)Adipicacid
Q. 31
(L)BF2/P
(ii)NaCN
> [X]
(iii)H20/H/A
^COOH
CH2-CO\^
Q. 3 2
/CO \
Which optically active compound on reduction with LiAlH4 will give optically inactive compound?
(A) CH3 - CH - COOH
OCH 3
OH
CH 2 OH
Q.33
OH
O
CH 3 - CH - C - CHR - CH,
,
2 3
CF3CQOOH
.
* [X] as main product
O
II
O
II
(B) C H 3 - C H - C - O - C H 2 - C H 3
CH 3
0
(C) CH3 - C - OC(CH3 ) 3
(fe Ban sal Classes
(D) (CH3)3COOCH3
Page # 7
Q. 3 4 Which one of the following reactions can be used for the preparation of (3-hydroxy acid:
(A) Perkin reaction
(B) Reformatsky reaction
(C) Aldol condensation
'(D) Claisen condensation
Q.3 5 Which acid can be oxidised be Fehling solution:
(A) Malonic acid
(B) Acetic acid
(C) Oxalic acid
[X]
Br
COOH
OOH
COOH
COBr
(D)
(C)
CJ
O
II
O
II
(A) - OH
(B) - C - H
Q.3 8 In the given reaction:
O
A o
'
(C)-C-OH
+ [X]
CH,
(B) CH3-CH2-CH2-CH2-COOH
(C) HO-C^-CI^-CI^-COOH
OH
Bansal Classes
Page #8
Q.3 9
* > [A]
0
NaBH 4
[B]
[A] and [B] respectively be:
O
(A) CH 2 OH - CH 2 - CH 2 - CH - CH 2 OH and I
OH
I
t)H
O
(B) f
and CH 2 OH - CH, - CH 2 - CH - CH 2 OH
OH
OH
A
(C) Both are I
J
OH
OH
(D) Both areCH.OH - CH 2 - CH 2 - CH - CH 2 OH
Q.40
COC 2 H 5
+ I
cooc
CH2^NH2
(A)[
(B)kN>0
/COOC2H5
"N=Cv-C00C2H5
N=c
(C)[
/COOC2H5
^OOC 2 H5
-NHO
^B ansa I Classes
CH 2
(D)CH 2
v
M r
iN =
/COOC2H5
^-COOC^Hg
Page # 9
CH,-COOH
(A)-
CH2-COOH
CH,-CH,NH,/A
>(B)
O
I!
O
(A) CH 2 -C-NH-C 2 H 5
(B)CH2-CCH, - C
2
II
o0
N-COH
2 5
^
CH,-COOH
(C)
(D) I
CH,-COOH
CH,-COOH
) ( A )
Fenton
>
( B )
/A
(B)RCOOAg
CH3
(C) CH3-CH3
(D) CH3-C-CI
CH,
Q. 44
(D) Claisen
Page #10
<jj
(A) Alkyl cyanide
(B) H - C - N '
.CH3
-CH3
Q.54 Which gas will be evolved out when [CH^O-LNT^ + (CH3)2CHNH2] is treated with sodium nitrite and
HCl:
(A) Chlorine
(B) Ammonia
(C) Nitrogen
(D)N0 2
Q.55 Boiling Ethylamine on reaction with acidified KMn04 gives:
(A)Acetaldehyde
(B) Ethanoic Acid
(C) Ethanol
(D)Acetamide
(C)(CH3)3N
(D)CH3NH2
Page #11
(C) Alcohol
(D) None
(D) Aldehyde
CI
300K
COOH
NH2
NC
(B)0
CI
(C,0
COOH
NH2
CI
( D
, 0
CI
C6H5-NHX
Q.70
cone HC1
C6H5-NH^
> A +
fi
Heat
(C) Phenol
(D)Diphenyl thiourea
Q
Q.72
rI V/ c N zH ^A W
Zis:
CH3MgBr
H3O
>X
O'^vppt.)
Ca(OH)
2 ,I 2
O
(A) [
C - CH3
(B) [ > C O O H
(C)
Bansal Classes
Page #12
Q.73
V
Y < ^ ^ - < f Q V c O O H
(")KOD,Br 2 A
(A) X is
Yis
(i)N 3 A
'
(ii)KOH,Br 2 A
( O ^
(C)both < ( C ? ) - N D 2
(D) both < ^ O y ~ N H 2
Q.74
ea(OH) 2 > CI 2
) X
J !
N O
> Z
(A) CH3CH2CH2NH2
(B) CH3CH2CH2OH
(C) CH3CHCH3
(D) CH3CH2COOH
OH
Q. 75
The bond angles in methane (I), ammonia (II) and trimethyl amine (III) increase in the order:
(A) I >111 >11
(B) I >11 >111
(C) II > I > III
(D) III > II > 1
<fIBansal Classes
(D) CH3COONH4
Page # 13
Q. 78
H3N-CH-C-NH-CH-C-OCH3
CH2
CH 2 Ph
(A)
O
O
I!
II
(A) H 2 N - C H - C - N H - C H - C - O C H 3
CH 2
CH 2 Ph
CO.
I
CH 2
I
CH 2 Ph
CO 2 H
O^nh^ci^COV
(C)
1
D
kru / ^ N H ^ - Q
PhCH
2
+ CH3OH
(A)L
Q. 8 0
(C)ULnhJ
The synthetic sweetener aspartame, known commercially as Nutra sweet, is carboxylic acid. In aqueous
solution on standing it changes to:
(AA
(C) \\
>
/F
//
<fIBansal Classes
NH
Page # 14
EXERCISE - KB)
Q. 1
QHXHO
6
5
>
CH3COONaA
H,-0
2
O H
( B ) CH3COOH
CVO
CH-CH2OH
T Y 4h
HO
CH,OH
(D> I 2
CH o 0H
HO
Q.3
Q.4
>
(B)RNCO
(C) RNHj
(D)None
Q.5
C4HJJN + HN0 2
> C,H]0O (3 alcohol)
(X)
hence X will give:
(A) carbyl amine reaction
(B) Hofmann mustard oil reaction
(C) diazonium salt (as the intermediate) withHN02
(D) base insoluble product with Hinsburg reagent
Q.6
Bansal Classes
Page #15
Q.7
CI + N H
(B) y ^ C l + 2NH3
>ONH
CI
> y m i 2 + NH4C1
( C ) ^ CI + N H 3 < ^ + N H 4 C I
(D)
+ HN0 2
Q. 8
Which of the following compounds will give acetic acid with KMn04/H/A:
(A) CH3-CHO
(B)CH3-CH=CH-CH3
(C) CH3-C=C-CH3
(D)CH3CH20H
Q.9
(D)ethanol
Q.10 Which one of the following acids will form acetyl chloride with PC15?
(A) MeCOOH
(B) MeCOOMe
(C) MeCOOCOMe
(D) Me-CONE^
Q.ll
ff
> CH,-C-O-CH3+HOH
(D)F2
Q.13 Which one of the following compounds will give HVZ reaction?
COOH
-COOH
(C) / - C O O H
Q.14
Sodium salt of which one of the monobasic acids on electrolysis does not give hydrocarbon:
(A) C6H5COOH
(B)HCOOH
(C) Me3C-COOH
(D) COOH-CH=CH-COOH
<fIBansal Classes
Page # 16
Q.15 Which one of the following acids undergoes decarboxylation on strong heating:
(A) Pyruvic acid
(B) 3-butenoic acid
(C) Formic acid
(D) Salicylic acid
Q.16 Which one of the following compounds is least reactive with water?
(A) CH3 - C - CI
(B)C6H5-C-NH2 (C)CH3-C-NH2
(D)C6H5-C-C1
(D)Anticeptic
O
II
R-C-OH
[X] will be:
(A)CH2N2
[X]
- R - C - O - CFL
(B)CH3OH/H
(C) MeCOOH
(D)Me 2 S0 4
(B) [CH3NH3] CI
(D)PhN0 2 ~
(D) CH3N+H3C1"
Q. 23 Which of the following compound can be produced if 1 -propane amine is treated with NaNO, and HCl
(A) Propane-l-ol
(B) Propane-2-ol
(C) 2-Chloropropane (D) 2-Propaneamine
Q. 24 Which of the following amine does not react with Hinsberg reagent to give base soluble product
(A) Neopentvl amine (B) secpropyl amine (C) diethyl amine
(D) Ethyl methyl amine
Q 25 Ethylamine can be prepared by
(A) Curtius reaction
(B) Hofinann reaction (C) Mendius reaction (D)Reduction offormaldoxime
Q.26 The presence of primary amines can be confirmed in laboratory by:
(A) Reaction with HN0 2
(B) reaction with CHC13 and ale. KOH
(C) Reaction with Grignard reagent
(D) Reaction with acetyl chloride
Bansal Classes
Page #17
Q.27
Q.28
R
Y^C(CH3)3
Y 0 H
+(CH 3 ) 3 COH
o
o
(A)(CH 3 ) 3 CO e (alkoxide) - a strong nucleophile is formed
(B) (CH3)3C (carbocation) is formed
(C)
/OH
11
(a weak acid) is formed
O
Column I
(organic compounds oxidised by HI0 4 )
(A)
CH 3 COCHO
(B)
1,2-cyclohexanedione
(C)
PhCH (OH) CHO
(D)
CH 3 CH 2 CH (OH) COCH 3
(D)
Q.29
Q.30
Column II
(products of H I 0 4 oxidation)
(P)
PhCH = O + HCOOH
(Q)
CH3CH2CHO + HOOCCH 3
(R)
HOOC (CH 2 ) 4 C00H
(S)
CH 3 COOH + HCOOH
Column I
Column II
(A) C 6 H 5 - C - OC 2 H 5 + H 3 C - C - 0 - C 2 H 5 ->
II
"
II
o
o
(P)
AnhydrousZnCL
(Q)
C 2 H 5 0,e
(R)
Red P
C 6 H 5 - c - CH 2 - c - O C 2 H 5 + C 2 H 5 O H
II
II
(B) H 3 c - C - OH + Cl2
o
C1CH2-C-OH
o
CH3
amines
Page # 18
Q 31
Column I
(Reagents reacting with PhCH 2 COOH)
(A)
CH 3 MgBr
(B)
PC15
(C)
NH 3 , followed by heating
(D)
CH 3 OH in the presence of conc. H 2 S0 4
Q 32
Column II
(Product formed)
PhCH 2 COCl
(P)
(Q)
PhCH 2 COOCH 3
(R)
CH 4 '
(S)
PhCf^CONHj
Column II (Products)
Column I (Reactions)
0
(A)
2CH 3 CH 2 NH 2 +
(P)
(oVN-CH-ZO)
(Q)
(CH 3 ) 2 N
o
II
S
(R)
o
II
(CH 3 ) 2 N-C
(B)
(CH 3 ) 2 NH + C 6 H 5 COCI
(oV
CHO + ^ ( J ^ - N H a
(C)
m
o
(D)
Q.33
Q.34
CH 3 CH 2 NH 2
S0 2 C1
(S)
C 2 H 5 NH - c - CH 2 CH 2 - C - O
Column II
Column I
(A)
R'NH 2
NaNO :jL HC U
(P)
RR'N-N= O
(B)
PhNH 2
NaN0
(Q)
Ph-N* = NCI
(C)
PhN(CH 3 ) 2
(R)
P)
RR'NH 2
(S)
^+HC1 >
Column I
(A) PhCONH 2
> PhCH 2 OH
(CH3)2N-<^O^N=0
R'OH + N 2
(P)
Column II
B2H6Ac0HH20
(Q)
LiAlH4
(R)
(S)
HjPd BaS0 4
None
O
0
(B)
CH 2 OH-(CH 2 ) 2 -CHOH-C 6 H 5
CM,
(C) C 6 H 5 CH = C H - COOH ->C 6 H 5 - CH = CH 2 OH
(D) CH3COCI
CH 3 -CHO
Q 35
Column I
Column II
(A) RCN
REDUCTION >
(B)RCN
(L)CH MGBR
->
(P)
1 Amine
(Q)
Alcohol
(R)
Ketone
(S)
Acid
(ii)H20
( O RNC (D)RNHh2
ii Ban sal Classes
HYDF0LYSIS
amines
Page # 19
EXERCISE - II
Complete the following
.....etc.
excess
Q.2
Ester (A) B
aqKOH
+C
H2/Pd BaS04
(D)
Q.3
R-COOH
Q.4
Mo stAg2
'
KCN
Q.5
ND,
H^O
soci.
Acid (A)
(CH 3 ) 2 CHCH 2 OH
Br,,KOH
(A)
>(B)
NaN02+HCl / p \
^^
- >C
E+NaCl
NaOH T g
Q-6
LiA1H
CO\
[ ZCO'
r n > - M ^
A.
PCI,
MeNH,L v> C
o
.ci
Q.7
O= <
/NH2
+
A - ^ O- ^
c
Q.8
CaCN 2 +
/NH-C-Me
+
B>0
(unede)
/NHSO3H
o = <
H O H - i ^ ( A ) - ^ ^ ^ ( B )
(H 2 0 2 )
COOH
COOH
A
COOH
COOH
>A
_A_>B
NTOOH
A
H
A
Q.10
Q.ll
p h
+B
COOH
/ = ^ .
C 0
4 I B a n s a l Classes
0 H
-U(
Carboxylic
)
Acids & It's Derivative
Aliphatic
amines
Page
#20
Q.12
PhMe + (A) p - M e C ^ - C Q - C H ^ a ^ C O O H
Q.13
CH 3 (CH 2 ) 1 4 CH 2 CH 2 COOH
(i)Ag+(ii)Br
CH 3 (CH 2 ) 1 4 COOH
Q.14
[ p T
> (A)
(A)
C 0 0 H
Zn/Hg/HC1
>(B)
2 >(D)
Hd
) (R)
_ic
L >
C H 2 C 0 0 H
f^n Y-^CH.COOH
+ C02+H20
COOH
qi5
COOH
O
I
CI
Q.16
Q.17
HC=CH
OH"
/ a\
OH" .
>(A)
>(B)
^ 2 N a > (A)
(ii)2C0 2
(i)H 2 0
(II)H30
2/Pd
BaS0 4
Q, 18
Phthalicacid + NHL
>D
>E
Q.19
MeCH(CH2COOH) 2
(CH3CO)2O
) F
o
Q.20
^^^
CH3-C-N~(
LiA1H4
> (A)
o
Q.21
[ P l y
LlA1H
" ) (B)
Q-22
R-C-NH2+
Q.23
0
R - C - OR' __NaOH_^RCOONa + R'OH
4IBansal Classes
"
>R-NH 2
Page #21
Q.25
RON,
ff
R - C - O H + HN3
2s4
o
II
>RNH2
o
A,CI
II
Q.26
R-C-Cl
)R-C-C6H5
Q.27
O
R - C - CI + CFLN2 >
R-CFL-COOH
(ii)H20
^Bansal Classes
Page # 22
EXERCISE - III
Q. 1
(a)
(b)
(c)
(d)
Show by a series of equations how you could synthesize each of the following compounds from the
indicated starting material and any necessary organic or inorganic reagents.
2-Methylpropanoic acidfromtert-butyl alcohol
3 -Methylbutanoic acidfromtert-butyl alcohol
3,3-Dimethylbutanoic acidfromtert-butyl alcohol
H02C(CH2)5C02H from H02C(CH2)3C02H
(e)
(f)
(S)
L / LN
Q.2
/Br
A
from
cyclopentyl bromide
from
(E)-C1CH=CHC02H
CO2H
rr"
C02H
Me
TR^O
I >CH2COOH
(I)H3Q+ O"
* I
LCH3
Suggest a reasonable mechanism for this reaction. What other organic product is also formed?
Q.3
Suggest reaction conditions suitable for the preparation of compound Afrom 5-hydroxy-2-hexynoic
acid.
CH3CHCH2C = CCO2H >
OH
r v
H,}"
5-Hydroxy-2-hexynoic acid
Compound A
Q. 4
(a)
A + BrMgCH9CH7CH,CH,MgBr
O O
"
n
Q. 5
HC xCH2CH2CH2OH
ya
O
(a)
(ii)H,0
C H 3 0 ^ ~ ^ ~ CC1 +
CCH
P - ^ U compound A (C22H1804)
OH
fe Bansal Classes
Page # 23
o
(b)
CH3CCH2CH2COCH2CH3 -
> c o m p ( ) u n d
( a l a c t o n G ;
C^O,)
COH
(c)
HOC
heat
Q.6
An organic compound C4H604 (A) when heated with acetic anhydride give another compound C4H403
(B) which in turn react with ammonia to give a third compound C4H502N (C). Both (B) and (C) may be
hydroiysed to A. With chlorine A give monochloro-compound (D) which reacts with caustic potash to
give either C4H405K2 (E) or C ^ O ^ (F) depending upon the condition of reaction. Identify the
compound A to F.
Q.7
An organic compound A (C4Hc,NO) on treatment with bromine and alkali form another compound B
(C3H9N) on treatment with sodium nitrite and dilute hydrochloric acid. B yield C (C3HgO). C can be
oxidized to D (C3H60). Which can also synthesisedfrommethyl acetylene. Identify the compound Ato D.
Q.8
With bromine and caustic potash the straight chain compound C4H9ON (A) give C3H9N (B), with
caustic soda C4H702Na (C) and with phosphorous pentoxide gives C4H7N (D). With hydrochloric
acid D give C4H802 (E) ofwhich C is the sodium salt. B may be converted to an alcohol (F) and then to
a halide the grignard reagent from which react with carbon dioxide to give E. On oxidation F give.
Identify the compound Ato H.
Q. 9
Compound (A) with an empirical formula, C7Hc,N on diazotization give a product which undergoes
reaction with Cu2Cl2 & HC1 to give a compound (B). B on oxidation give a compound (C). Compound
(A) on treatment with Br2/H20 form C7H6NBr3 (D). Give the structural formula ofA, B, C & D.
Q.10 An organic compound A (C3H5N) on boiling with alkali give ammonia and sodium slat of an acid B
(C3H602) A on reduction give a compound 0 (C3H9N) which with nitrous acid give D (C3HgO). Give
the structural formula ofA, B, C and D.
Q.ll
An organic compound (A) C3H?ON on heating with POCl2 give a compound B which on hydrolysis
give a compound (C) C3H602 with the liberation of ammonia. Compound Aon treatment with LiAlH4
form compound C3H9N (D). Compound D treating with HN0 2 liberate N2 gas on refluxing with
chloroform and alcoholic KOH give compound E which have foul smell. Identify compound A,B, C, D
and E.
Q. 12 An organic compound A (C8HgO) an treatment with NH2OH. HC1 give B and C. Compound B and C
can be converted into D and E respectively by treatment ofH 2 S0 4 . Compound B, C, D and E are all
isomer of molecular formula CgF^NO. When D is boiled with KOH, and oil F (C6H7N) separate out.
F react rapidly with CH3COCl to give back (D). On other hand. E on boiling with alkali followed by
acidification give a white solid G (C7H602). Identify Ato G.
Q.13 An organic compound A, (CgH9NO) on heating with conc. H 2 S0 4 give another isomer of (A) i.e. (B)
C8H9NO. Compound B on hydrolysis with dil HC1 give an aliphatic acid C, C2H402 and (D) on
treatment with NaN02 HC1 at 0C give a compound (E) which give a white ppt. of AgCl on addition of
AgN03. Compound (E) react with alkaline (3-naphthol to produce orange dye what are to E.
Q.14 An organic compound A of the molecular formula C4Hg03 give effervescence with sodium bicarbonate
solution and can be acetyl ated. It can be separated into dextro and laevoisomers on heating it forms an
acid B with formula C4H602. Compound B give positive Bayer's test. Identify A and B.
fe Bansal Classes
Page # 24
Q.15
An aromatic compound A, CgH5N02 can be condensed with an acid derivative (B) C 7 H,,0 4 Br in
presence of alkali to form compound (C), C15H15N06. Compound (B) can be prepared by action of
sodium followed by bromine gas on diethyl malonate. Compound (C) condensed again with ethyl chloro
acetate in presence of sodium to give compound (D) C19H21N08. D on heating with a base can be
converted into E and a salt of acid F (CgH604). Compound A can be obtained by heating F with
ammonia. E on boiling with mineral acid produce amino acid G (C4H7N04). Identify Ato C.
Q.16 An organic acid A(C3H403) is catalytically reduced in presence of ammonia to give (B) C3H7N02. B
react with acetyl chloride hydrochloric acid and alcohol. It can also react with nitrous acid to give
another compound (C) C3H603 along with evolution of N2. What are (A), (B) and (C)?
Q.17
A dibasic acid (A), C4H606, on heating with KHS04 give a monobasic acid (B), C3H403, with the
elimination of C0 2 and H 2 0. Acid (B) on reduction give another monobasic acid (C), C3H603. Both
(B) and (C) on heating with I2 and NaOH solution give yellow precipitate of iodoform and sodium
oxalate. Acid (A) react with two moles of acetyl chloride, while (C) reacts with one mole of acetyl
chloride. Acid (A) reacts with four moles of HI to form succinic acid, while (C) react with two moles of
HI to give propionic acid. Identify A, B, C and give equation for reaction.
Q.18
An organic compound of the formula C3H60 (A) gave iodoform test but not Tollen's and Fehling tests.
Two molecules of (A) condenes in presence of dry HCl gas to yield (B) of formula C6H10O. Compound
(B) decolourised Br2/CCl4 and cold dilute neutral KMn04, but no ppt. with ammonical AgN03 or
CuCl solution. It gave iodoform test and potassium salt of a compound on heating with I2 and KOH. The
potassium salt on treatment with H 2 S0 4 gave compound (C) of formula C5H802. Compound (C) on
heating with sodalime gave (D) of formula C4Hg. Identify compound Ato D & write the chemical
equation.
Q.19 An organic compound (A) of formula C3H6Qfroma monoxime with hydroxylamine and form iodoform
on heating with I2 and NaOH and sodium acetate. Compound A on reaction with NaCN and dil. H2S04
gave product B. Which on hydrolysis produced (C). Compound (C) on heating gave (D), which on
decarboxylation gave (E) of formula C3H6. Compound (E) on ozonolysis gave one molecule of
acetaldehyde and one of methanal. What are Ato E?
Q.20 Two moles of an ester (A) are condensed in the presence of sodium ethoxide to give a P-keto ester (B)
and ethanol. On heating in an acidic solution (B) gives ethanol and J3-keto acid (C). On decarboxylation
(C) gives 3 -pentanone. Identify (A), (B) and (C) with proper reasoning. Name the reaction involved in
the conversion of (A) to (B).
Q.21
An acidic compound (A), C4Hg03 loses its optical activity on strong heating yielding (B), C4H602
which reacts readily with KMn04. (B) forms a derivatives (C) with SOCl2, which on reaction with
(CH3)2 NH gives (D). The compound (A) on oxidation with dilute chromic acid gives an unstable
compound (E) which decarboxylates readily to gi ve (F), C3H60. The compound (F) gives a hydrocarbon
(G) on treatment with amalgamated Zn and HCl. Give structures of (A) to (G) with proper reasoning.
Q. 22 An organic compound (A), C5H803 on heating with soda-lime gives (B),which reacts with HCN to give
(C). The compound (C) reacts with thionylchloride to produce (D), which on reaction with KCN gives
compound (E). Alkaline hydrolysis of (E) gives a salt (F), which on heating with soda-lime
produces -butane. Careful oxidation of (A) with dichromate gives acetic and malonic acid. Give structures
of (A) to (F) with proper reasoning.
Q.23
An acid (A), C g H ? 0 2 Br on bromination in the presence of FeBr gives two isomers, (B) and (C) of
formula CgH602Br2. Vigorous oxidation of (A), (B) and (C) gives acids (D), (E) and (F) respectively.
(D), C7H502Br is the strongest acid among all of its isomers, whereas (E) and (F) each has a molecular
formula of C7H402Br2, Give structures of (A) to (F) with justification.
fe Bansal Classes
Page # 25
EXERCISE - IV (A)
O
Q.l
The
reaction
of
R-C-NH 2 with a mixture of Br2 and KOH gives R-NH2 as a product. The
(A) R-C-NHBr
Q.2
(B)R-N=C=0
[BIT 1992]
II
(C)R-NHBr
(D)R-C-N<
Br
[IIT 1995]
.1
OH
NH2
Q. 3
The molecular weight of benzoic acid in benzene as determined by depression infreezingpoint method
corresponds to :
[IIT 1996]
(A) Ionization of benzoic acid
(B) Dimerisation of benzoic acid
(C) Trimerisation of benzoic acid
(D) Solvation of benzoic acid
Q.4
When propionic acid is treated with aqueous NaHC03, C0 2 is liberated. The 'C' of C0 2 comes from
(A) Methyl group
(B) Carboxylic acid group
(C) methylene group
(D) bicarbonate
[IIT1999]
Q.5
Q. 6
[IIT 2000]
(D^HJO
^OCQCH3
P
Acidic
Q.7
Hydrolysis
Q.8
[IIT 2004]
(D) Benzylamine
Q. 9
Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodium acetate?
[IIT 2005]
(A)CH3-<fy-COONa
(B) CH3
7 + S0 3
(C) CH3 ~ f
(D) CH,
CH3
fe Bansal Classes
V s oS0r 3NNa
a +CHXOOH
+ CHgCOOH
Page # 26
[IIT 2006]
Which ofthe following reactants on reaction with conc. NaOH followed by acidification gives the following
[IIT 2006]
lactone as the only product?
O
\>
/
CH 7
<a
COOCH3
COOH
COOH
<b>OC
\
COOH
c c
CHO
cc
COOH
EXERCISE - IV (B)
Q.l
Compound (A) (C6H1202) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound
(B) on oxidation gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E).
The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F)
which was found to be monobasic acid (molecular mass = 60.0). Deduce the structure of (A), (B), (C),
[IIT 1990]
(D)and(E).
Q.2
In the following reactions, identify the compounds (A), (B), (C) and (D)
PC15 + S0 2 ->(A) + (B)
(A) + CH3COOH
> (C) + S0 2 + HCl
2(D) + CdCL
2(C) +b (CHACd -
[IIT 1994]
Q.3
[IIT 1995]
(i)
CH,CH,COOH
;f2
>
(A)
(i)Alc.KOH(excess)
(g)
(ii)H
(ii)
C4H03(A)
(B)
Q.4
A mixture of an acid anhydride (A) and a monobasic acid (B) on heating produces another monobasic
acid (C) of equivalent weight 74 and an anhydride (D). The acids and anhydrides remain in equilibrium.
The anhydride (D) contains two identicalfluoro-alkylgroups. The acid (B) contains a trifluoromethyl
group and has an equivalent weight of 128. Give structures of (A) to (D) with proper reasoning. (Atomic
weight of fluorine =19).
[HT 1998]
Q.5
[IIT 1999]
H3C^^cooc2H5
CH
\COC2H5
.(A)"
.(B)
(i)OH~
(ii)H + A
fe Bansal Classes
CH--C-OH
2
II
o
Page # 27
Q.6
[IIT 2000]
O
CH3-C-O18C2H5
Q. 7
H3 +
>A+B
Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H 2 C*0) as one of the products when compound Z is treated with HBr and
BaC*0 3 +H 2 S0 4
>C (gas) [C* denotes C14]
[IIT 2001]
CH22 = CH - Br
( )Mg/ether
'
(II)X
(iii)H30+
Q. 8
Mention two esters pro duced when a racemic mixture of 2-phenyl prop anoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters?
[IIT 2003]
Q.9
[IIT 2004]
CH2-C1
f /-N 1
(
KCN
DMF
V A
(i)NaOEt/EtOH
(ii)PhCHO/ A
>n
n
H,0
socl2
(ii) CH 3 NH 2
Page # 28
ANSWER KEY
EXERCISE -1(A)
Q.l
Q.8
Q. 15
Q.22
Q.29
Q.36
Q.43
Q.50
Q.57
Q.64
Q.71
Q.78
Q.l
Q.2
Q.3
Q.4
B
C
D
B
C
B
A
B
D
B
C
C
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.52
Q.59
Q.66
Q.73
Q.80
C
c
B
A
A
A
A
B
C
B
A
C
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
Q.53
Q.60
Q.67
Q.74
B
C
C
A
C
A
D
D
C
B
C
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
Q.55
Q.62
Q.69
Q.76
C
B
A
A
A
B
C
C
D
C
A
Q.7
Q.14
Q.21
Q.28
Q.35
Q.42
Q.49
Q.56
Q.63
Q.70
Q.77
A
C
A
A
B
B
B
A
C
D
C
C
D
A
B
D
B
A
C
A
A
D
C
Q.2
Q.9
Q.16
Q.23
Q.30
Q.37
Q.44
Q.5I
Q.58
Q.65
Q.72
Q.79
Q.l
Q.5
Q.9
Q.13
Q.17
Q.21
Q.25
Q.29
Q.30
Q.32
Q.34
EXERCISE - KB)
Q.4
A,B,C,D
A,B
Q.2
A,B,C
B,C
Q3
Q.8
A,B,C,D
A,C,D
Q.6
A,B,C
A,C
Q7
Q.12 A,B
A,B,C,D
Q.10 A,B,C
Q.ll A,B
Q.16 B
Q.14 B,C
Q.15 A,B,C,D
B,C
Q.20 A,B,C,D
Q.18 A,B,D
Q.19 A,B,C,D
A,B,C
Q.24 A,B
Q.23 A,B,C
Q.22 D
A,B,C
Q.28 B
Q.26 B
Q.27 D
A,B,C
(A)S,(B)R,(C)P,(D)Q
(A)Q, (B)R,(C)P,(D)S
Q.31 (A) R, (B) P, (C) S, (D) Q
(A)Q,(B) S, (C)P,(D)Q
Q.33 (A) S, (B) Q, (C) P, (D) R
(A)S,(B)Q,(C)S,(D)R
Q.35 (A) P, (B) R, (C) P,S, (D) Q
Q5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
Q.54
Q.61
Q.68
Q.75
A
C
A
B
D
C
C
C
A
C
A
EXERCISE - II
(A) CH3CH(OOCCH3)2; (B) CH3CHO; (C) (CH 3 C0) 2 0
(A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHC0C1; (C) (CH3)2CHCH2C1
(A) RCOND2; (B) RNH2; (C) ROH
(A) CHgCl; (B) CH3OH; (C) HCOOH; (D) Ca(OH)2; (G) HCHO; (H) CH3C1; (I) KCN; (J) CH3CN;
(X)CH 3 COOH
Q.5
Q.6
Q.7
Q.8
CH-,
\
NH"
"C
ft
rooH
S
Q. 10(A)
H
M
COOH
(B)
o
II
[
Q.9
(A)k
Q 11
(A)
;(B)[
Ph-
.00
-C"
II
o
Carboxylic Acids & It's Derivative Aliphatic amines
Page # 29
Q.12
(A)
Q.13
Q14 (A
> tOXc,oH;
(B
>
^lcH2cr(C)
CN
:c=o
^ o t -(D) tOD 1
Q.l 5(A)
00H
;(B)
COOH
COOH
Q.17
Q.16
H COOH'
H-C-COOH
C COOH
ONH 4
(D)[0
Q.20
(A)CH 3 CH2NH-
H - C - C O O H ; (C)
Q.18
COOH
(A)
-ONH4 ;(E)
y N-H
(D)
N^T+COOH
^
Q.19
(F)
;(C)
C 0
COOH
XTH-CO^
^
Me
H'
CH 2 OH
Q.21
CH 2 OH
EXERCISE - III
CH 2 COOH
Q.6
(A)
CH2CO\
(B)
CH 2 COOH
CH2CO/
Succinic anhydride
CHCOOK
Succinic acid
(E)
CH 2 (OH)COOK
(F)
CH 2 COOK
CH7CO\
(C) !
> H
CH2CO/
Succinimide
CH 2 CICOOH
(D) I
CH 2 COOH
CHCOOK
Potassium maleate
Q.7
(A) (CH 3 ) 2 CHCONH 2 ; (B) (CH 3 ) 2 CHNH 2 ; (C) (CH 3 ) 2 CHOH; (D) CH 3 COCH 3
Q.8
Q.9
Q.10
Q. 11
CI
) f O L
CH,
(B)fOl
CH,
CI
.(C) [ O
COOH
, (E)CH 3 CH 2 CH 2 N = C
amines
Page # 30
0
Q.12
C-CH3 ; ( B ) r f ^ r C = N - O H c ) r ^ [ - C = N
;(
(A)
C-NH-CH,
(E)
(E)FO
;(D)
0
II
C-OH
o
II
N H - C - C H 3 ; (C) CH3COOH;
C = N-OH ;(B)
(A)^Q
O
|f>rNH-C-CH
(G)
CH3
Q.13
CH3OH
CH,
2Cr
OH
Q.14
N_H;
Q 15 (A)
COOEt
COOEt
Q.17
Q.18
Q.19
Q.20
Q.21
Q.22
^N-CH(COOEt) 2 ;
COOEt
-CCHXOOEt.
Q.16
C-OH
C-OH
<i00Et
(E)
-COOH
-Br
Br
(7-OpCH 2 COOH
; (B) B r j O J - B r
(F)
i (9 f O
2rnOH
-Br
iV^VCOOH
' (D)[UJ-Br
lOjBr
Page # 31
Q.l
Q.8
A,B
A
Q.2
Q.9
A
C
Q.3
EXERCISE - IV (A)
Q.4
D
Q.5
Q.6
Q.7
EXERCISE - IV (B)
Q. 1
Q.6
Q.7
(i)Mg,(ii)C*Q 2
CH 2 =CH-C*OOH(Y)
CH 2 =CHC*H 2 OH(Z)
CH 2 =H-C* H J <
(iii)H30+
LiA1H
H+
>
>
> C* H 2 CH=C*H 2
I Br
iBr
CH 2 =CH-C*H 2 Br BrCH2 - C H ^ C * ^
I 0 3 ZNH 2 0
I O ^ n f ^ O Br-C*H 2 CHO + HCHO Br-CH 2 CHO + HC*HO
H
Ph
Q.8
'
(+)CH3CH2-C-OH
I
I
CH3-C-COOH + CH3-C-COOH
|
CH,
conc.H2S04,A
Ph
(racemic mixture)
Ph
H
I
I
CH3-C-C-0-C-CH2CH3 +
'
! I
I
'
H 0
CH 3
H
H
I
I
CH3-C-C-O-C-CH2CH3
I II
I
Ph O
CH 3
during esterification reaction only -COOH and - O H partcipates. There is no effect on structure or
configuration of carbon adjacent to these groups. So when() acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers of each other.
CN
9VCN
Q.9
<A)(g)
CH=C^O)
( B ) ^
CONHCH3
COOH
CH=C-(p)
(Ofgs
CH = C
( D ) ^ ^ ,
amines
Page # 32
ORGANIC CHEMISTRY
XII (ALL)
CONTENTS
EXERCISE-I
EXERCISE-II
EXERCISE-III
EXERCISE IV
ANSWER KEY
EXERCISE-I
(Choose the correct option. Only one is correct)
Q.l
XH
(A>
<$2
>
\/\/
Q A
C , < X > c d
sj^. 3
( C )
( B ) Q e
Cf)
(D)CH 2 =CH
2-chloropentane on halogenation with chlorine gives 2,3, dichloropentane. What will be the structure of
free radical species form in the reaction?
(A) Planar
(B) Trigonal planar
(C) Square planar
(D) Pyramidal
What will be maj or product, when 2-methyl butane undergoes bromination in presence of light?
(A) 1 -bromo-2-methyl butane
(B) 2-bromo-2-methyl butane
(C) 2-bromo-3-methyl butane
(D) 1 -bromo-3-methyl butane
The smallest compound, which on photochlorination produces diastereomers is
(A) 3-methyl, 3-chloro hexane
(B) 2-chloro butane
(C) 1 -bromo propane
(D) 1 -bromo-3-methyl butane
Q.6
Q.7
Q. 8
> 1116 ma or
J P roduct i s
Cl-v
(A)
Cl-\
HO
(B)
OEt
EtO
)
EtO
(C)
[\*
OH
OEt
(D)
Ph
J&
L>CH3
CT
H3O+
Phv.
(A)
Ph\
|
HOA^CHS
R
^Bansal
Classes
>?
(B)
Ph^
I
HO^YCHA
OH
(C)
|
R
OH
Halogen Derivatives
[2]
* /^v-OH
^0710 I J
(A)
(B)
(C)
OH
(D)
Q.12
a ) O O H
(iv)
conc.H 2 SQ 4
Br,
) X
170 a C
(A)
alc.KOH
> y
CC1-
> z
CH,
H,C3
( B ) H
C - ^
HO
Q.13
( C ) H
OH
C ^
( D ) H
C - ^
CH
CH2
O
(i)Na0Br
C6H5-CH-CH2-C-CH3
>product
(ii)H20/H+
(iii)A
product will be
OH
O
II
(C) C 6 H 5 - C - CH 3 , C0 2 and CHBr3
C1F2CX
tt/
/ F
c=C
OEt
C1F2CX
(A)
(l5
/=C
Ph
|\:H 3
O ^ S .
(A)
.OEt
(B)
F
CHs
H+
J>C
PhX
/ F
OEt
(C)
> - 9 Ph
I
p h
C1F2CX
(D)
OEt
/ F
>
<
X
C H
k X !
faBansal Classes
CIF2CV
CH3
(C)
Halogen Derivatives
CH3
(D)
0 H
^ A x
C H 3
[3]
-ex
Q.17
NaOBr
Product
The product is
<oc
o c ~ o .
CH,
nu
/OH
(A) V
JCH-
<&<
/OH
( O /OH~\
TA
(D)
OH
J?.f9
'OH
Which one of the following alcohol will undergo acid catalysed dehydration with greatest ease by E,
mechanism?
(A)CH2 = CH-OH
(B)!"]
(C)
T
OH
0C2O
(A) C 3 H 6 0
NaCN
(D)Me2CHOH
OH
> cyanohydrin of (A). Ifthe cyanohydrin is optically active, then the possible
H 2 SO 4
structure of (A) is
(A)
.
( B ) ^
(C)P>-OH
(D) |
sj^.22
LL
J)
ROH/H+
(B) CH3CHO
O
II
O
II
(q
(d)
^Bansal Classes
QH3
OR
Halogen Derivatives
0
[4]
Q.23
C1 3 -CH = CH2
H3CCH=CH2
(I)
(II)
(B) Br is at C2 in II and at C, in I
(D) Br is at C j in both cases
Q.25
1 equivalent Mg
ether
^Br
(A)\
> X
(B)\
(C) [ ^ B r "
>
Y; Y is
(C)\
How many number of optically active isomers are possible for 2,3-dibromo butane 1,4-dioic acid?
(A) 2
(B) 3
(C)4
(D)l
~<K Q-27
yN
and
n-^
(B) Position
(C) Metamerism
(D) functional
( ^ H ^ C / ^ ^ ^ v /
.CH,
H3C
CH3
(B).
H3CV
H3CV
(C)H3c^/CH
H3C
x &30
H3C
.CH,
(D)
H
(A)
A
H3C
(C)
/K/0**
V
HO
(B)
CH,
faBansal Classes
CH3
H3c
/ V C
OH
CH,
3
(D)
OH
CH
Halogen Derivatives
[5]
(A)
( B )
A
'OH
( O h , C ^
(D)
(a)
^CH
CH3SN/CH3
<b) f o J C H 3
fo)
C H
CH3XN/CH3
(c)
(o)
(D)
3 \
[ o
CH3
3 In which ofthe following molecule all the effect namely inductive, mesomeric & hyperconjugation operate
( A ) < ^ - C 1
) \ _ / "
C H
( C ) ( > C O C H 3
CH3
(D)<
CH,
+ C l e , AH
(II) O c ,
>
(III)
^)-CH2CL
(IV) { >
C 1
+ Cl , AH
>
^-CH
+ CI, AH3
> { ^ y + CI , AH
Jtr
(A)1>2>3
faBansal Classes
(B)2>1>3
(C) 2>3>1
(D)3>2>1
Halogen Derivatives
[6]
Q.36
One of the configuration of n-butane is drawn in the given figure. Anticlockwise rotation of C2 around
C 7 -C, bond by 120 will lead to
CH3
(A) gauche
(B) staggerred
t-
p.
(IV) Br
(III) N 3
Arrange decreasing order of reactivity of these compounds for nucleophilic substitution reaction
O
II
(I) CH3 - CH2 - O - S - CF3
o
(III) CH3 - CH - CH3
(IV) CH3 - CH - OH
OH
(A) III, IV, I, II
tBansal
Classes
C6H5
(B) III, IV, II, I
X^41
X 3 < H
(A)
HOv /
H
H 3 + O H
\ 7CH3
X^_y\H
(B)
'
H\
A i S
\ /CH3
(C)
Ph
Q.42
CH3
alc.KOH
CI.
A, A is
Ph
ch3^C6H5
(A)
CH3\ /C6H5
(B)
^C6H5
C6H5-
CfiH<
^C6H5
o<i
o c
s /
CI
46
OEt
EtOH
>
(C) IV<III<II< I
<-Qc
RateR
Rate R2
EtOH
EtOH
Oc.
R-OEt
vX5
RateR3
(C)R2>R,>R3
Among the foloowing pairs in which case the second compound has higher heat of hydrogenation.
(A) |
||, [ f ^ ]
(C)
faBansal Classes
(B) Cis-2-butene,trans-2-butene
Halogen Derivatives
[8]
Q A ^ (I)
-Br
Q.49
\^TC(CH3)3
CH3SNa
^0H > ?
OH
SCH3
(C) CH3SCH2CH-C(CH3)3
OH
OH
Q.50
(C)3<4<1<2
(D)3>4>1>2
y
J
f"
^ci
)CH
=CHCHCH
( I ) C H 3 C 2 CCH 3
CI
(A) I > II > III
^Bansal Classes
CI
(C> II > III > I
Halogen Derivatives
[9]
EXERCISE-II
(iChoose the correct option. One or more than one are correct)
O.l
/f
\ = /
which is/are incorrect statements?
P
Q
(A) P is cis- and Q is trans(B)PisZandQisE
(C) P is R and Q is S
(D) P and Q are having same structural formula
Q.2
Q.3
Q.4
(D) geometrical
(C) tautomerism
CHCOOH
(A)
(C)
m -
CH 3
(D)CH3-C-NH,
o
Q.5
CH 3
CH 3
A
V
CH 3
\ /
CH 3
I
II
I and II are not
(A) achiral-identical mirror images
(C) geometrical isomers of each other
Q.6
(B) chiral-enantiomers
(D) racemic mixture
(B) (
OH
(C) CH 3 - CH - CH 2 - COOH
(D) CH 3 -CHCOOH
OH
Q.7
\=0
S
PCH
CH 3
HOOC
CH 2 COOH
Q.8
Classes
Halogen Derivatives
[10]
Q.9
C5Hg04 (A)
Sodahme
C 4 H 8 0 2 (B)
> (C)
O
II
oc
Q-io
ch 3 -o^^CH-CH 3
3+ >
^ = 0 and 0=^
) are enantiomers
O .
CI
CH3
are enantiomers
H
CH2CH3
(C) Argol (sodium potassium tartarate) will show optical isomerism.
(D) CH3CHO on reaction with HCN gives racemic mixture.
Q.12 Which is/are less acidic than Benzoic acid?
(A)CH3COOH
(B)(0)"cooh
3
Q.13
(C)\O/-C00H
NO2
(D)H 2 0
Q.14
(B) CH3-CH2-NO2
( O V
^Bansal Classes
Halogen Derivatives
[11]
Q.15
The unshared electron on the oxygen atom of an ether (basic centre) account for all the following except:
(A) Combination
C2H5N.
> 6=
F
|
B- F
c,H 5
/ cr
Which ofthe following compounds yield most stable carbanion after rupture of (CJ-C2) bond:
0
II
II
1 2
1 2
II
1 2
Q.17
N
pyrrole (I)
pyridine (II)
which is/are correct statements ?
(A) I is more basic than II
(C) ID is more basic than II
Q.18
aniline (III)
(B) II is more basic than I and III
(D) all are aromatic bases
/OH
(D)CC13CH<"
^011
is unstable.
(A)<0)-Br
(B) <^0)-CH=CH-CH 2 Br
(C)|
(D)(>- B r
Or-
1
II
(A) I & III are antiaromatic
(C) II alone is aromatic
Q.21
III
Oiv
^Bansal Classes
(B)(0>-<OH
(D) NaNH2
Halogen Derivatives
[12]
Q.22
Q.23
Q.24
Q.25
The acid strength of substituted carboxylic acids is known to be dependent on the nature and position of
the substituent. In the following examples, an attempt has been made to arrange the acids in order of acid
strength, the strongest first. One of the series is incorrect-which one?
(A) CH3.CH2CH(Cl).COOH > CH3.CH(Cl).CH2COOH > CH3.CH2.CH2.COOH
(B) NO2.CH2.COOH > HOCH2.COOH > CH3.COOH
(C) Cl3C.COOH > BrCH2.COOH > FCH2.COOH
(D) CH3.COOH > CH3.CH2.COOH > (CH3)3C.COOH
Q.26
(A)BCI3
Q.27
(B) N H ;
(C)CH 3
(D)AlCi;
(D)C1C=CC1
Which of the following structures represent the less stable tautomeric form?
(A)ch3ch2cK
F^ 8^ o c h
.ch3
(B)
Qo
H
H
H(X
YH
(D)
C = C
o
Q.28
(A)
(B)
X I
H3CN
(C)
Q.29
Q.30
C/
H
C = 0
( D ) H 3 C
In tautomerism
(A) a proton is moved around the molecule
(C) no actual movement occurs
CH3
Q.31
ON
(B)O
(c)Cjn
(wt>
N9
6 Bansal
Classes
GOC
FXERC1SE-1II
Q. 1
Arrange the following compounds in decreasing order ofKeq for hydrate formation.
O
C 6 H 5 COCH 3
CI^O)-
(!)
C H
(2)
0
o
N02-<O>-^CH3
CH3^0>-C-CH3
(3)
^Q.2
>
f
I
Ph
<
1
CI
^ P h
Q
(II[)
aD
av)
(P)
an)
(b) Explain which of these reactions would have the faster rate?
CH3
(i) CH3CH2CH2 + CH 3 N:
CI
^J^A
(a)
>
or
(ii) CH3CH2CH2
+ CH 3 NH 2
>
C1
CH3
>
(b)
CH 3 -CH = N = N
Q. 5
Arrange the isomers of molecular formula C4H9C1 in order of decreasing rate of reaction with sodium
iodide in acetone.
>
Q. 6
I
(b)
(c)
CI
I
Q.7(i)Choose the member of the following pairs of unsaturated hydrocarbons that is more reactive towards
acid-catalysed hydration and predict the regiochemistry of the alcohols formedfromthi s compound.
(b)
(a)
(c)
(I)
I or
(n)
^ ^ ^ or
(I)
(II)
(ID
(ii) Predict on the basis of cabocation stability, which member of each of the following pairs hydrolyses at
the faster rate.
Jr
(a)
Br
Br
or I
(I)
Br
(ii)
Assuming that cation stability governs the barrier for protonation in H - X additions, predict which
compound in each ofthe pairs in parts (a) to (b) will be more rapidly hydrochlorinated in a polar solvent.
(I)
(II)
(a)
CH2 = CH2
or
Q .9
or
a)
(o[Q
Q. 8
(b)
(H)
<o>
(O
Select the member of each pair that shows faster rate of SN2 reaction with KI in acetone.
CH3-CH2-CH2-CH2-C1
or CH3 - CH - CH2 - CI
CH3
(I)
(II)
CH3 - CH2 - CH2 - CI or CH3 - CH2 - CH2 - CH2 - Br
(I)
(II)
CH,
J0T
CH3
(II)
(I)
Br
(d)
CH3-CH2-CH2-CH-CH3
^Bansal Classes
Br
or
CH3 - CH - C % CH - CH3
CH3
Halogen
(P)
Derivatives
[15]
Q.10 Select the member of each pair that undergoes SN1 solvoysis in aqueous ethanol more rapidly.
CH3
^iaf
or
CH 3 -C-C1
ch3
ch3
^Jcf
ch3
CH 3 -C-C1
or
CH3 - C - Br
ch3
ch3
r^YBT
.Br
(d)
Q T
or
Q.ll
(a)
(b)
(c)
(d)
(e)
(1)
Q.12
In each ofthe following indicate which reaction will occur faster. Explain your reasoning.
CH3CH2CH2CH2Br or CH3CH2CH2CH2I with sodium cyanide in dimethyl sulfoxide.
1 -chloro-2-methylbutane or 1 -chloropentane with sodium iodide in acetone.
Hexyl chloride or cyclohexyl chloride with sodium azide in DMF.
Solvolysis of 1 -bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol.
Reaction of 1 -chlorobutane with sodium acetate in acetic acid or with sodium methoxide in methanol.
Reaction of 1 -chlorobutane with sodiumagde or sodium p-toluenesulfonate in aqueous ethanol.
Classify each of the following species as electrophile or nucleophile & explain your choice.
(a)CH3C02-
(b)CH30-
(c)BF3
(d) CI
(e) CMe3
(g)SiF4
(h)Br
(i) :P(CH3)3
G)Me2CH
> H
0H
" > I
> J
Ca( H)2
)K
(f):CCl2
^Q.13
Propene
<x^Q:l 4
(a)
(b)
(c)
(d)
,(e)
(f)
(g)
- (h)
) L(glycerol)
l^/Q-1 5 Of the following statements which are true for SN1 reaction.
(a)
Tertiary alkyl halides react faster than secondary.
(b)
The absolute configuration of the product is opposite to that of the reactant when an optical active
substrate is used.
(c)
The reaction shows first order kinetics.
(d)
The rate ofreaction depends markedly on the nucleophilicity ofthe nucleophile.
(e)
The mechanism is two step.
(1)
Carbocations are intermediate.
(g)
Rate oc [Alkyl halides]
(h)
The rate of the reaction depends on the nature of the leaving group.
Halogen Derivatives
[16]
^Bansal Classes
x + CH 2 = CH 2
AH 2
X C H , - C H2
X C H 2 - C H 2 + H - X - > XCH 2 CH 3 + x
I
HQ
HBr
HI
All are in kJ mole '.
-67
-25.1
+46
+12.6
- 50.2
-117.1
Q.24 CHC1,F is found to react more slowly than CHC1, in alkaline hydrolysis with plausible mechanism.
Illustrate this phenomenon.
vaoA*-**Q.25 Formulate the reactions between but-l-ene in presence of small amount of benzoyl peroxide &
(i)CCl4
(ii)CBrCl3
Give your reasons.
Q.26 p-Amino benzaldehyde behaves like an amide as is evident by the fact that it is not readily attacked by
the nucleophile at the carbonyl carbon. Explain.
Q.27 When CH3MgBr react with 5-chloro-2-pentanone, cyclic ether is formed instead of alocohol. Explain.
Q.28 The dichlorocarbene reacts with electron rich species like phenol where as it doesn't reacts with benzene
explain.
tBansal
Classes
GOC
]l7J
Why is elimination preferred to hemiacetal formation in the acid catalysed cyclisation ofthis ketone ?
0
Q.31
-OCX
o
D1
'
^ o
( Cyclic ester)
*a
(lactone)
MeOH
Q.33
C X ^ y <
cone.
OH
H2SO4
> r
Y<f+H20
Q.34 The reaction of cyclopentyl bromide with sodium cyanide to give cyclopentyl cyanide
f y H
k / \ r
NaCN ) ,
ethanol-water
r \ H
Cyclopentyl bromide
Cyclopentyl cyanide
proceeds faster if a small amount of sodium iodide is added to the reaction mixture. Can you suggest a
reasonable mechanism to explain the catalytic function of sodium iodide?
Q.35 The reaction of 2,2-dimethyl-1 -propanol with HBr is veiy slow and gives 2-bromo-2-methyl-propane
as the major product.
CH,
CH3CCH2OH
CH3
Q.36
CH,
Br
1 -Bromobicyclo [2.2.1 ] heptane
Halogen Derivatives
^Bansal Classes
[18]
Cte ^ CC3
2,2-Dimethylcyclohexanol
O^to
CH3
1,2-Dimethylcyclohexene
Isopropylidenecyclopentane
Q.3 8 When 2-bromo-2,3-dimethylbutane reacts with a base under E2 conditions, two alkenes (2,3-dimethyl1-butene and2,3-dimethyl-2-butene) are formed.
(a)
Which of the following bases would give the highest percentage of the 1 -alkene ?
(b)
Which would give the highest percentage ofthe 2-alkene"
CH3
CH2CH3
CH3CO~
CH3CH2CO~
CH3
CH3
CH3CH20_
CH3CH2CO~
CH2CH3
CH3
^Q.39 Dr. Don T. Doit wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion
and 2-chloro-2-methylpropane for his synthesis and ended up with very little ether. What was the
predominant product of his synthesis ? What reagent should he have used ?
Q .40 The following reaction takes place under second-order conditions (strong nucleophile), yet the structure
of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than
the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism
to explain the enhanced rate and rearragement observed in this unusual reaction. ("Et" is the abbreviation
for ethyl.)
Et2N:
:NEt2
H2C-CH-CH2CH3
"OH )
CI
OH
*Q.41 When ethyl bromide is added to potassium t-butoxide, the product is ethyl t-butyl ether.
CH3CH2 - Br + (CH3)3C - 0~ +K
> (CH3)3C - O - CH2CH3
ethyl bromide potassium t-butoxide ethyl t-butyl ether
(a)
What happens to the reaction rate if the concentration of ethyl bromide is doubled ?
(b)
What happens to the rate ifthe concentration ofpotassium t-butoxide id tripled and the concentration of
ethyl bromide is doubled ?
*
(c)
What happens to the rate if the temperature is raised ?
Q. 42 Give a mechanism to explain the two products formed in the following reaction.
Hx /CH 3
X
C = c XCH3
/
H
%
H\
3-methyl-l-butene
^Bansal Classes
Br
NBS,hv
H\
X
C-C
H/
\h
CH3
X
CH3 +
not rearranged
Halogen Derivatives
I ^ C " C H3
BrC-C
H
I
H
rearranged
X
[19]
Q.4 3 Give the structures of all possible products when 2-chloro-2-methylbutane reacts by the El mechanism.
Q .44 Solvolysis of 1,2-dimethylpropyl p-toluenesulfonate in acetic acid (75C) yieldsfivedifferent products:
three are alkenes and two are substitution products. Suggest reasonable structures for thesefiveproducts.
Q.45 Solution A was prepared by dissolving potassium acetate in methanol Solution B was prepared by
adding potassium methoxide to acetic acid. Reaction of methyl iodide either with solution A or with
solution B gave the same major product. Why ? What was this product?
Q .46 Solvolysis of2-bromo-2-methylbutane in acetic acid containing potassium acetate gave three products.
Identify them.
Q.47
(a)
Write the structures or build molecular models of all the isomeric alkyl bromides having the molecular
formula C5HnBr.
(b)
Which one undergoes E1 elimination at the fastest rate ?
(c)
Which one is incapable of reacting by the E2 mechanism ?
(d)
Which one can yield only a single alkene on E2 elimination ?
(e)
For which isomers does E2 elimination give two alkenes that are not constitutional isomers ?
(f)
Which one yields the mobt complex mixture of alkenes on E2 elimination ?
Q.48 Evidence has been reported in the chemical literature that the reaction
(CH3CH2)2CHCH2Br + KNH2
> (CH,CH2)2C - CH2 + NH3 + KBr
proceeds by the E2 mechanism. Use curved arrow notation to represent the flow of electrons for this
process.
Q.49 The given compound give mixture of six products on treatment with CH3OH. Write structures of all five
products and give mechanism of the reaction.
Q.50 Comment on the selectivity, (that is, say what else might have happened & why it didn't) shown in this
grignard addition reaction used in the manufacture of an antihistamine drug, A.
CI
Q. 51 Outline an efficient synthesis of each of the following compoundsfromthe indicated starting material and
any necessary organic or inorganic reagents:
(a)
Cyclopentyl cyanidefromcyclopentane.
(b)
Cyclopentyl cyanidefromcyclopentene.
(c)
Cyclopentyl cyanidefromcyclopentanol.
(d)
Isobutyl iodidefromisobutyl chloride.
(e)
Isobutyl iodidefromtert-butyl chloride.
(f)
Isobutyl azidefromisopropyl alcohol
Q. 5 2 Select the combination of alkyl bromide and potassium alkoxide that would be the most effective in the
synthesis ofthe following ethers:
^Bansal Classes
Halogen Derivatives
[20]
ch
3'k/a >
CH3
CH3
(b)
CH3-CH2-CH2-C-N(CH3)3OH^->
CH3
CH3
(c)
(d)
>
(CH
3>3COK >
Q.54 Choose the compound of molecular formula C7H13Br that gives each alkene shown as the exclusive
product of E2 elimination.
(a) ( 3
(b)(^CH2
CH,
(d)
r A
(6)
k/cH3
L ^ C H = CH2
( c)<>CH3
/CH(CH3)2
(f)|Q
(g)J^C(CH3)3
^
Qx5 5 Select the alkyl halide and a nucleophile that will give each ofthe following products.
CH3 - CH2 - CH2 - NH2
t/(fT) CH3 - CH2 - O - CH2- CH3
(c)CH = C-CH 2 -CH 2 -CH 3
Jdf(CH3)2CHS(CH3)2
Je)C6H5-0-CH2-CH3
Q. 5 6 Identify the product in each of the following reactions:
(a) C1CH2CH2CHCH2CH3 - i ^ ! l - > C 5 H 1 0 C l I
CI
(b) BrCH,CH2Br + NaSCH2CH2SNa
> C4HgS2
(c) C1CH2CH2CH2CH2C1 + Na2S
C4H8S
Q. 5 7 Write the structure of the principal organic product to be expected from the reaction of 1 -bromopropane
with each ofthe following:
(a) Sodium iodide in acetone.
O
v (b)
GOC
12U
(e)
- ( C H
- C H
>
Jbf
- C I - ^ >
CI
(d)
Na0H
>
>
Q. 5 9 Draw each of the following reaction in a way that clearly show the stereoisomerism of the products.
H
(a)
CH3
me
CH3 - C - Br + CH3ONa
C H
- C H
01
>
(b)
NaSH
SN1
(c)
BrCCA
hv
CC14 hv
C
Give a mechanism for each of the reactions.
Q. 61 Complete the following reactions. Give all possible products in each case. Give mechanism ofthe reactions.
C H 3
(a)
(b)
Moist A g 2 Q )
CH 2 -CI
^CH2C1
HOWA
>
CH - CH, - CH,
Q.63
) (A)
alc
f H > (B)
(C) -
Peroxide
LlF
DMF
> (D)
CH3-CH2-Br
> (A)
CH3-CH2-Br^ (B)
ci2/hv
)+(
)+(
( c ^ c S f
>
( F ) + ( G ) + ( H )
(0I2/NaOH/A
(ii) H
> ( A ) +
( B )
o
(b) r v
\
c
/
c h
(i)Br2/ a H
(ii) H
(c)| > - C H O H - C H 3
>(Q+(D)
(i) CaOCl^/HOH
>
( E )
( F )
(ii) H
Na0H/F
^ >G +H
CI
faBansal Classes
Halogen
Derivatives
[22]
Q.65
(a)
C 6 H 5 - CH - CH 3 + NaCl + HOH
Electrolysis
Br
XI
(b)
C6H5-CH
aq.NaOH
-CI
(b)
>A
H3C
/c
= c
\N
+HI
>B
+ HC1
>D
CH,
(c) l ^ J
Peroxide
+ HBr
>C
(d)
CH2CH3
PhC 5= CH + Br2
CH3
Br,
(c)
Q.67
H-tO
(b)
w
CH33 CH,CH
= CH,
2
2
(A\
VC =- nCH
u2
K )
H3C
H?0
Br
>
Na0H
2 v>
"2
v>
(i)EtMgBr
(ii)ph2C0
CI
A
(b)
ale.KOI 1 ^
S02C12
(i)PhLi
(ii)C02 ,(iii)H /H 2 0
(iii) NH4C1
Mg/Et2Q
Q.68
CH3CH2CH2C1
Q.69
CLC - <!! - OH + Na
Q. 70
O
II
(i)CH3-C-CH3
) p
-B
H2SQ4/A
(ii)aq.NH4Cl
'
<
MeOCHjCl
BuLi
>A
CHBft
BuOK
CHt-CHO
->9
N^CO.E.
Ph - CH = CH
ABansal Classes
GOC
[23]
EXERCISE-IV (A)
^pd
Reaction of R-CO-NH2 with a mixture of Br2 and KOH gives R-NH2 as the main product. The
[JEE 1992]
intemediates involved in this reaction are:
(A) R-CO-NHBr
(B)RNHBr
(C) R-N=C=0
(D) R.CO.NBr2
[JEE 1993]
Which one of the following has the smallest heat of hydrogenation per mole?
(B) trans-2-Butene
(A) 1-Butene
(D) 1,3-Butadiene
(C) cis-2-Butene
In the following compounds:
[JEE 1996]
OH
OH
NO,
(HI)
(I)
v^4
Q.7
[JEE 1998]
(B)CH H CHBr
O
O OH
(D) CH CH CHBr -TV.
^~Br
(C) CHXHBrCH.
o
A solution of (+) 1 -chloro-1 -phenylethane in toluene racemizes slowly in the presence of small amount
(A) CHXHBrCH
Q.5
[JEE 1999]
(D) carbocation
[JEE 1999]
[JEE 1999]
O
(B) C H 3 - C - C H 3
OH
OD
Q.9
^Bansal Classes
Halogen Derivatives
[24]
[JEE 2001]
NH2
(1)
(A) 2 > 1 > 3 > 4
Q.ll
CH3CNH
(3)
(C) 3 > 1 > 2 > 4
(4)
(D)L
Identify the correct order of reactivity in electrophilic substitution reaction of the following compounds:
(1)
(A)1>2>3>4
^12
(2)
(B) 1 > 3 > 2 > 4
(CH3)2NH
(2)
(B)4>3>2>1
(3)
(4)
(C)2>1>3>4
[JEE 2 0 0 3 1
(D) HOC-CH=CH 2
(D)CH3C1
[JEE 2003]
(C)CH2C12
COOH
Q.14
when X is made to react with 2 eq. of NaNH2 the product formed will be:
[JEE 2003]
(A)
(C)
fa Bansa!
Classes
GOC
[25]
Q.15
Order ofrate of reaction of following compound with phenyl magnesium bromide is:
Ph-C-Ph
Me-C-H
I!
O
II
o
(I)
Hs
Q.16
II
o
(II)
[JEE 2004]
Me-C-Me
(III)
(C)III>I>II
YVV53
[JEE 2004]
COOH
X
1 -Bromo-3-chloro cyclobutene on reaction with 2-equivalent of sodium in ether gives [JEE 2005]
<B
Cf
(A) j
.CI
(D)
(C)
JSO
O ,3H
H
f o l
Q.18
CH 3 COONa(excess)
[JEE 2005]
(absolution)
SO2COOCH3
(B)
(A)
Me
COONa
S0 3 Na
(C)(0)
+CH3COOH
(D)lOJ
Me
+H 2 S0 3
Me
[JEE 2005]
[JEE 2005]
CH,
CH,
(A)
(B)CH3-C-OPh
CH,
^Bansal Classes
OH
(C)
Halogen Derivatives
CH,
(D) CH3 - C - Ph
CH,
[26]
Q.21
For 1 -methoxy-1,3-butadiene, which of the following resonating structure is the least stable?
(A) H 7 C- CH- CH = CH - O - CH,
(B) H 2 C- CH = CH - CH = O - CH3
(C) H2C = C H - C H - C H - 0 - C H 3
CH3 H
Q.22
^5}"N02
MCO-^5^H
CH3
[JEE 2005]
CI CH3
(K) M e O ^ O ^ H
-<p)-
(A) K & L
Q.23
CH3 H
N0
(L)MeO-<g>
OH CH3
CH3 H
(M) MeO-^O)-
CH3
CH3
- ^ Q } -NO,
OH H
CH3
CH3
-(O)-^02
CH 3 OH
(B)only
(C)Monly
(D) K & M
When benzene sulfonic acid and p-nitrophenol are treated with NaHC03, the gases released respectively
are
[JEE 2006]
(A) S0 2 , N0 2
(B) S0 2 , NO
(C) S0 2 , C0 2
(D) CO2, CO2
CH3NH2 + CHC13 + KOH - Nitrogen containing compound + KC1 + H20. Nitrogen containing
compound is
[JEE 2006]
(A) CH3-C s N
^25
(B) CH3-NH-CH3
(C) CH3 - N = C
(D) CH3 N = C
fa Bansa! Classes
GOC
[27]
OM
(i)
H2N^Q-CI
(ii)
(iii)
< N H Q - C I
(vi)
(v)
(iv)
In this reaction, RCONHBr is formedfromwhich this reaction has derived its name. Electron donating
group at phenyl activates the reaction. Hofinann degradation reaction is an intramolecular reaction.
How can the conversion of(i) to (ii) be brought about?
(A)KBr
(B)KBr + CH3ONa (C) KBr + KOH
^27
Q.28
[JEE 2006]
(D) Br2 + KOH
\-NH2
(A) > = /
D
)=/
(i)
\-NH2
'\=/
(ii)
R V - NH,
N
(B) Q
> =- N
/ H 2 )' Q
W- M H 2
D
(C) i
(C)
\-NH 2 $
(D) ^ y - N H D ) ^ y
^Bansal
Classes
\-NH;
[JEE 2006]
Halogen Derivatives
[28]
EXERCISE-IV (B)
CH3CH2CHC12
Q.2
C 6 H 6 + (CH3)2CHCH2C1
Q.3
( O V C O O ^ O )
Q. 4
\ _ y
"1-KOH
[JEE 1991]
Q. 1
>
a1c1
[JEE 1992]
3 >?
[JEE 1993]
monomtration
[JEE 1994]
CNH<
_H
BR-
NaOH
>
SM2
CH,
Q. 5
Complete the following, giving the structures of the principal organic products:
[JEE 1997]
+ KNH 9
(a)
(b)
\\
(c)
Q. 6
C 6 H 5 CH(OH) C=CH
/ I + CHBr 3 +1 - BuOK
>B
H,0
>C
[JEE 1998]
> C 6 H 5 CH = CH-CHO
o c r ^ o a ,
Q.7
Each of the following reaction gives two products. Write the structure of the products.
(a)
C6H5CH2CHC1C6H5
(b)
CH 3 CONHC 6 H 5
Q.8
Out of anhydrous A1C13 and hydrous A1C13 which is more soluble in diethyl ether? Explain with reason.
[JEE 2003]
Q.9
AlcK0H A
'
Br
2.Fe
[JEE 2003]
Acid
3.3 x 10"5
(a)
(ii)
4.2 x 10"5
(b)
Me-^^-COOH
Cm)
6.3 xlO"5
(C)
C ^ C O O H
(iv)
6.4 x 10"5
(d)
MeO^COOH
(v)
30.6 x 10~5
(e)
COOH
fa Bansa! Classes
[JEE 1998]
>
<0)-COOH
GOC
[29]
Q.10
[JEE 2003]
V
OH
Q.ll
[JEE 2004]
.o.
Q.12
Predict whether the following molecules are iso structural or not. Justify your answer.
(i)NMe3
(ii)N(SiMe3)3
[JEE 2005]
Q.13
Give reasons:
[JEE 2005]
H,C
(a)
Br
(0
(ii) B
_ / " \ _ y
\ = /
(b)
c2H5OH(aq.)
^ acidic solution
CH,
(i)0,
C2H5OH(aq.)
) neutral
rCH,
Na H(aq)
^V
>F (liberated)
CH,
(ii)
NaOH(aq.) . p i s n o t liberated
H,C
H2N02
(c)
Conc.HNOg
(i)
Conc.H2S04
NO,
NO,
NO,
(ii) I
(d)
faBansal Classes
Conc.HNO
Conc.H2S04
NO,
Halogen Derivatives
[30]
Q.10
[JEE 2003]
V
OH
Q.ll
[JEE 2004]
NH 3
OJ
IC>
Q.12
Predict whether the following molecules are iso structural or not. Justify your answer.
(i)NMe3
(ii)N(SiMe3)3
[JEE 2005]
Q.13
Give
[JEE 2005]
reasons:
H3C
(a)
Br
CH3
CH
(ii)Br-7^W
\=j
rCH,
(b)
C2H5OH(aq.)
Na H(aq)
(Oo.N^V
>
neutral
> F (liberated)
CH,
(ii)
NaOH(aq.)
p is not liberated
H,C
CH 2 N0 2
.0
(c)
Conc.HNO,
(i)
Conc.H-.SO
2JU4
>
N02 +
|
NO,
NO,
NO,
(ii) I
(d)
faBansal Classes
Conc.HNQ3
Conc.H2S04
NO,
Halogen Derivatives
[30]
NaBr+Mn 2
Q.14
[JEE 2005]
H a . - I w
[JEE 2005]
where is the dipole moment of stable conformer and x{ is the fraction of that conformer.
Write stable conformer for Z - CH 2 - CH 2 - Z in Newman's projection. If psolutjon = 1.0 D and mole
fraction of anti form = 0.82, find
Write most stable meso conformer of CHD Y
I
CHDY
If (i) Y=CH 3 about C 2 - C 3 rotation and
(ii) Y=OH about Cl - C 2 rotation.
faBansal Classes
Halogen Derivatives
[31]
ANSWER KEY
Q.l
Q.8
Q.15
Q.22
Q.29
Q.36
Q.43
Q.50
D
D
C
A
A
A
A
D
Q.2
Q.9
Q.16
Q.23
Q.30
Q.37
Q.44
Q.51
Q.l
Q.5
Q.9
Q.13
Q.17
Q.21
Q.25
Q.29
C
B,C,D
C,D
A,C,D
B,D
A,B,C
C
A,D
C
A
A
C
C
A
A
D
EXERCISE-I
Q.4 B
Q.ll A '
Q.18 B
Q.25 D
Q.32 B
Q.39 B
Q.46 C
Q.53 C
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.52
B
B
B
C
B
C
A
C
Q.2
Q.6
Q.10
Q.14
Q.18
Q.22
Q.26
Q.30
EXERCISE-II
A,D
Q.3
A,B,D
Q.7
A,B
Q.ll
C,D
Q.15
D
Q.19
B,C
Q.23
A,C,D
Q.27
B
Q.31
Q.5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
B
C
C
A
C
D
C
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
A
C
A
D
B
B
C
A,B,C,D
A,B,D
A,B
D
B,D
A,B
A,B,C
D
Q.4
Q.8
Q.12
Q.16
Q.20
Q.24
Q.28
A,B,C,D
C
A,D
A
A,C
A,C
D
Q.7
Q.14
Q.21
Q.28
Q.35
Q.42
Q.49
A
C
D
C
B
A
A
EXERCISE-III
Q.l
3 >2> 1 >4
Q.2
IV>I>II>III
Q.3
Q.4
(a)
Q.5
Q.6
Q.7
(i) (a) II, (b) I, (c) II ; (ii) (a) II, (b) II, (c) I
Q.8
Q.9
Q .11
Q 2.1 I
Q.14 b,d,e,g,h
Q .15 a,c,e,f,g,h
Q.45 MeCOOMe
OAC
Q.46
C - C - C - C , C-C = C-C, C - C - C - C
C
C
c
c
c
(f)
Br
C-C-C-C-C
faBansal Classes
Halogen Derivatives
[32]
Q.50
C
Q.53
( a ) C - C - C = C - C ; ( b ) c - C - C - C = C 5 (<0 C = C - C - C ; (d) C - C - C - C = C
C
Br
Q.54
(a)
(f)
CH,Br
; (b)
B r ^ '
; (c) B r - - ( ^ ) - C H 3
(d) L y ^ ; ( e ) Q > - C H 2 - C H 2 - B r
^[^-CMes
Q.55
Q.56
; (c)
CI
Q.57
(a)
; (b)
Q.58
(a) C 6 H 5 -CH 2 -CH 3 -CN, (b) <^>-SCH 3 , (c) CH 3 -<CH 2 ) 9 -I, (d) <ON-ch 3 I 0 , (e)
H
Q.59
; (<
; (d) / ^ C N ; (e)
Me
a)CH30-C-CH3;
(b)
Me
Et-C-OMe + MeO-C-Et,
Pr
CH 2 CH 3
; (f) ^ / S H ; (g)
(c)
Pr
SH
Q.60
(A)RCH 2 CH 2 SR
Q.62
CH 3 -CH 2 -CH 2 -F
Q.64
(a) CHI 3 +(CH 2 ) 4 (COOH) 2 , (b) CHBr 3 +Q-COOH, (c) CHCl 3 +[>-COOH, (d) CHF 3 + EtCOONa
Q.65
(a)CHCl 3 , (b)PhCHO
faBansal Classes
(B)RCHBrCH 2 CCl 3
(C) RCHC1CH2CC13
Halogen Derivatives
[33]
Q.66
(d) \
^
Et
Br
Et-CH-CH2-Cl,
(df)
OH
Q.67
Ph
ph
I
^k/COOH
(a) Ph - C = C - C - Ph; (b) f O j
Ph
Q.68
Me 2 C=CH-CH=CH 2
Q.69
A::CC1 2
Q.70
(i)
& Ql>-
A, C
B, C, D
C
D
C
D
Q.2
Q.7
Q.12
Q.17
Q.22
Q.27
B:
CI
CI
0 M e
; (ii) r h
A , COOEt
EXERCISE-IV
Q.l
Q.6
Q.ll
Q.16
Q.21
Q.26
Q.3
Q.8
Q.13
Q.18
Q.23
Q.28
D
D
A
C
A
D
EXERCISE-IV
C(CH3)3
Q.l
CH 3 CH 2 CHO
Q.2
[ Q
Q.3
CH,
Q.4
C6H5-C-CH3
(A)
Q.4
Q.9
Q.14
Q.19
Q.24
D
D
D
C
D
B
D
B
B
A
C
(B)
^COO-Q^
Br
Q.5
Q.5
Q.10
Q.15
Q.20
Q.25
B
D
C
A
D
, v(C)J
II /
Ph-C-CHCH,
CH,
faBansal Classes
Halogen Derivatives
[34]
Q.6
C6H5-CH-CeeCH
> C 6 H 5 - C H - C = C H 5 ^ - > C 6 H 5 - C H - C = CH
OH
OH
C 6 H 5 - CH = C = CH
+
C 6 H 5 - CH = C = CH
I
OH 2
H2
> C6H5 - C H = C = C H
OH 2
tautomerism
, C 6 H 5 ~CH=CH-CHO
"
-FT
o^ch
" - c r X:H 3
H
NHCOCH 3
Q.7
(a)
(Major)
(b)[
NHCOCH 3
+r
l^JJ
j
Br
Q. 8
Anhydrous A1C13 is more stable then hydrous A1C13 because it is having vacant 3p orbital ofA1 which can
accept lone pair of electrons from oxygen of diethylether.
Q.9
Q.10
compound.
Q.12
Not. NMe 3 is trigonal pyramidal while N(SiMe 3 ) 3 is trigonal planar due to back bonding.
faBansal
Classes
Halogen Derivatives
[35]
CH.3
Q.13 (a) (i) H5C6 - C - OC2H5 + HBr(acid); (ii) no reaction due to partial double bond character
CH,l3
(c) (i) due to presence of lone pair of nitrogen atom NO group is electron denating and ortho, para
directing
O2N>
-OH
H
CH3
faBansal Classes
GOC
[36]
[[organic c h e m i s t r y !
XII (ALL)
HALOGEN DERIVATIVES
CONTENTS
EXERCISE-I (A)
EXERCISE 1(B)
EXERCISE-II
EXRECISE-III
EXRECISE-IV(A)
EXERCISE IV(B)
ANSWER KEY
EXERCISE-I (A)
(Choose the correct option. Only one is correct)
Qlf Which one is liquid at room temperature:
^
(A)CH3C1
(B)C2H5C1
(C)CH3Br
^L
Q?f
Q.4
Q. 6
(D)C2H5Br
The correct order ofmelting and boiling points ofthe primary (1 ), secondary (2) and tertiary (3) alkyl
halidesis:
(A)P>S>T
(B)T> S>P
(C) S > T > P
(D)T>P>S
Pick up the correct statement about alkyl halides:
(A) They show H-bonding
(B) They are soluble in water
(C) They are soluble in organic solvent
(D) They do not contain any polar bond
What would be the product when neopentyl chloride reacts with sodium ethoxide:
(A) 2-Methyl-2-butanol
(B) Neo pentyl alcohol
(C) Both 1st & 2nd
(D) 2-Methyl-2-butene
Reduction of alkyl halide by LiAlH4 is the type of reaction:
(A) Nueleophilic substitution reaction
(B) Electrophilic substitution reaction
(C)Electrophilic Addition reaction
(D) None of these
2-methyl butanoic acid is formed by the reaction CHC13, NaOH and
(A) Propene
(B)Ethene
(C)l-Butene
(D)2-Butene
Q.7
o
Q.12 CH3MgBr + CH2 = CH - C - H
OH
(A) CH2 = C H - C - H
CH3
(C) CH3-CH2-CH2-CHO
faBansal Classes
OH
(D) None is correct
Halogen Derivatives
[2]
Q.31
n-CjgH^Br + HC =CNa
n BuLi
>A
> B
H /Imc ar scat
Q.32
(i)
CHjCH^CHjOH
(ii)
CH3CH2CH2I
PBr
3 > (A)
Alc K0H
h+/h
> (B)
2 > (B)
HBf
socl
p6roxybenzoicacid
>F
NH
> (C)
? > (D)
2 > (C)
(D)
LiAlH4
(iii)
(iv)
CHgCH^MgBr
Alc K 0 H
Light
CH CHQ/H
> (B)
HBr
> (C)
AlcKOn
> (C)
> C^-CHj-CHj-Cl
(b) CHg-CHj-CHj-Cl
> CH3-CH-CH3
in single step
CI
CH Br
(c)(^J
C1
(d) ^ J j
> j^j
/"\^ C H 2 C 1
> [^J
O
I!
(e) Ph - CH2 - C - CI
Ph - CH^ - CI
O
(QPh-CHj-Cl
(!Bansal Classes
> Ph - CH2 - C - CI
Halogen Derivatives
[19]
EXERCISE-III
Q.l
A primary alkyl halide (X) C4H4Br reacted with alcoholic KOH to give (Y). (Y) reacts with HBr to give
(Z) an isomer of (X). On reacting with alkali metal such as sodium/dry ether gives (S) CgHj8 which was
differentfromthe compound produced when n-butylbromide was treated with Na. What (X), (Y), (Z)
and (S).
Q.2
On electrolysis an aqueous ethanoilc solution of so dium chloride gives sweet smelling liquid (X). (X)
gives isocyanide test and condenses with acetone tofromhypnotic (Y). What are (X) and (Y)?
Q.3
The alkyl halide C4H9Br (A) reacts with alcoholic KOH and gives an alkene (B), which reacts with
bromide to give dibromide (C). (C) is transformed with KOH & sodamide to gas (D) which forms a
precipitate when passed through an ammonical silver nitrate solution. Give the structure formulae of the
compounds (A), (B), (C) and (D) and explain reactions involved.
Q.4
An unsaturated hydrocarbon (A) C6H10 readily gives (B) on treatment with NaNH2 in liquid NH3.
When (B) is allowed to react with 1 -chloropropane, a compound (C) is obtained. On partial hydrogenation
in the presence of Lindlar catalyst, (C) gives (D), C9H18. On ozonolysis (D) gives 2,2-dimethylpropanal
and 1 -butanal. Give structures of (A), (B), (C) and (D) with proper reasoning.
Q. 5
One mole of each bromoderivative (A) and NH3 react to give one mole of an organic compound (B).
(B) reacts with CH3I to give (C). Both (B) and (C) react with HN02 to give compounds (D) and (E),
respectively. (D) on oxidation and subsequent decarboxylation gives 2 -methoxy-2-methylpropane.
Give structures of (A) to (E) with proper reasoning.
Q.6
A chloro derivative (A) on treatment with zinc-copper couple gives a hydrcarbon withfivecarbon
atoms. When 'A' is dissolved in either and treated with sodium, 2,2,5,5-tetramethylhexane is obtained.
What is the original compound A?
Q.7
A primary alkyl halide (A) C4HjBr reacted with alcoholic KOH to give (B). (B) reacts with HBr to give
(C) an isomers of (A). (A) on reacting with sodium gives (D) CgHlg which was differentfromthe
compound produced when n-butylbromide was treated with Na. What are (A), (B), (C) and (D).
Q. 8
One mole of a hydro carbon (A) reacts with 1 mole of bromine giving a dibromo compound C5HJ0Br2.
(A) on treatment with cold dilute alkaline KMn04 solution forms a compound C5H1202. on ozonolysis
(A) gives edquimolar quantities of propanone and ethanal. Deduce structure of (A).
Q.9
A hydrocarbon (A) was found to contain 85.7% carbon and 14.3% H. This compound consumes 1
molar equivalent of hydrogen to give a saturated hydrocarbon. 1 g of (A) just decolourised 3 8.05 of 5 %
solution by weight of Br2 in CC14. Compound (A) on oxidation with conc. KMn04 gave a compound
(C), C4HgO and (B) acetic acid. Compound (C) can easily be prepared by the action of acidic aqueous
mercuric sulphate on 2-butyne. Deduce (A), (B) and (C).
Q. 10 When a hydrocarbon (A) is treated with excess of hydrogen chloride, a dihalogen derivative (B) is
obtained. The compound (B) is treated separately with aqueous and alcoholic KOH to give compounds
(C) and (A) respectively both having three carbon atoms. Compound (C) does not reduce Tollen's
reagent and compound (A) give white precipitate with ammonical silver nitrate. Assign structures to
compounds (A) to (C).
^Bansal Classes
Halogen Derivatives
[20]
Q.ll
An organic compound (A) C7H)5C1 on treatment with alcoholic caustic potash gives a hydrocarbon (B)
C7H14. (B) on treatment with ozone and subsequent hydrolysis gives acetone and butyraldehyde. What
are (A) and (B). Explain reactions.
Q.12 A dihalogen derivative (A) of a hydrocarbon having two carbon atoms react with alcoholic potash and
forms another hydrocarbon which gives a red precipitate with ammonical cuprous chloride. Compound
(A) gives an aldehyde when treated with KOH (aq). What is (A)?
Q.13 A white precipitate was formed slowly when AgN03 was added to a compound (A) with molecular
formula C6H13C1. Compound (A) on treatment with hot alcoholic KOH gave a mixture of two isomeric
alkenes (B) and (C) having formula C6H,2. The mixture of (B) and (C) on ozonolysis furnished four
compounds (i) CH3CHO, (ii) C2H5CH0, (iii) CH3COCH3, (iv) (CH3)2CH. CHO
What are (A), (B) and(C).
Q.14 0.369 g of a bromo derivative of a hydrocarbon (A) when vaporized occupied 67.2 mL at NTP. (A) on
reaction with aqueous NaOH gives (B). (B) when passed over alumina at 250 C gives a neutral compound
(C) while at 3 50C it gives a hydrocarbon (D). (D) when heated with HBr gives an isomer of (A). When
(D) is treated with dil. F^SO^j, (E) is obtained. Identify (A) to (E) and explain the reactions.
Q.15 An organic compound (X) on analysis gives 24.24 % C, 4.04% H. Further sodium extract of 1.0 g of
(X) gives 2.90 g ofAgCl with acidified AgN03 solution. The compound (X) may be represent by two
isomeric structures (Y) and (Z). (Y) on treatment with aqueous KOH solution gives a dihydroxy compound,
while (Z) on similar treatment gives ethanal. Find out (X), (Y) and (Z).
Q.16
0)
(ii)
(Hi)
(iv)
(I%Bansal Classes
Halogen Derivatives
[21]
EXERCISE-IV (A)
Q.l
, Qrf
^
Chlorination oftoluene in the presence of light and heat followed by treatment with aqueous NaOH gives
(A)o-cresol
(B)p-cresol
(C) 2,4-dihydroxytoluene
(D) Benzoic acid
[IIT 1990]
Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to
(A) The formation ofless stable carbonium ion (B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbon attached to the halogen
[IIT 1990]
1-Chlorobutane on reaction with alcoholic potash gives:
(A) 1-butene
(B) 1-butanol
(C)2-butene
(D)2-butanol [ITT 1991]
The products of reaction of alcoholic AgN02 with ethyl bromide are
(A) Ethane
(B) Ethyl nitrite
(C) Nitroethane
Q.5
Q.7
<^8
Q.9
[ITT 1991]
(D) Ethyl alcohol
When nitrobenzene is treated with Br2 in presence ofFeBr3 the major product formed is:
m-bromonitrobenzene. Statements which are related obtain the m-isomer are
(A) The electron density on meta carbon is more than on ortho and para position
(B) The intermediate carbonium ion formed after initial attack of Br+ at the meta position is least
destabilized.
(C) Loss of aromaticity when Br+ attacks at the ortho and para position and not at meta position
(D) Easier loss of H+ to regain aromaticityfromthe meta position thanfromotho and para positions.
[ITT 1992]
Arrange the following compounds in order ofincreasing dipole moment
Toluene
m-dichlorobenzene
o-dichlorobenzene
p-dichlorobenzene
I
II
III
IV
(A) I < IV < II < III (B) IV<I<II<III
(C) IV<I<III<II (D) IV<II<I<III
[IIT 1996]
In the reaction of p-chloro toluene with KNHj in liq. NH3, the major product is:
(A) o-toluidine
(B) m-toluidine
(C) p-toluidine
(D)p-chloraniline
[IIT 1997]
(CH3)3CMgCl reaction with D 2 0 produces:
(A) (CH3)3CD
(B)(CH3)3OD
(C)(CD3)3CD
(D) (CH3)3OD [IIT 1997]
Benzyl chloride (CgHjCH^C^canbe preparedfromtoluene by cMorinationwith:
(A) S02CI,
(B) SOClj
(C)C12
(D)NaOCl
[IIT 1998]
0.10
Toluene, when treated with Br2/ Fe, gives p-bromotoluene as the major product, because the CH3
group
[IIT 1999]
(A) is para directing
(B) is meta directing
(C) activates the ring by hyperconjugation
(D) deactivates the ring
0Cfl
The order ofreactivity ofthe following alkyl halides for a S ^ reaction is:
(A) RF > RC > R-Br > R-I
(B) R-F > R-Br > R-Cl > R-I
(C) R-Cl > R-Br > RF > RI
(D) R-I > RBr > R-Cl > R-F
^Bansal
Classes
Halogen Derivatives
[ITT 2000]
[22]
Identify the set of reagents / reaction conditions 'X' and 'Y in the following set of transformation:
CH3 - CH2 - CH2Br
>
Product
[IIT 2003]
CH,
CH2CH3
(A) HO-
[IIT 2002]
" CH2CH2CH3
(B) HO-
-CH 2 CH 3
CH2CH3
CH2CH3
CHjCH^
CH3
(C) HO-
(D) HOCH,
CH 3 '
CH,
Column II
(P) El reaction
(Q)E2 reaction
(R) El cb reaction
(S) First order reaction
EXERCISE-IV
Q.l
(a)
jvf
Q.2
(B)
[IIT 1992]
Amongst three isomers of nitrophenol, the one that is least soluble in wateris_
[IIT 1992]
[IIT 1993]
CI
CgHj CH2 CH - CH3
KOH A
->
(ii)
C6H5COOH + CH 3 MgI-
Q.3
An alkyl halide X of formula CfiH]3Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H12). Both alkenes on hydrogenation give 2,3-dimethylbutane. Predict the structures
ofX, YandZ.
[IIT 1996]
faBansal Classes
>9+ ?
Halogen Derivatives
[23]
Q. 4
Predict the structure of the intermediates/products in the following reaction sequence - [ET 1996]
Br
HMeOPh
Q.5
_AicohaiicKOH^
Heat
H1(excess)
(b)
(CH3)2CHOCH3
Q. 6
Heat
[IIT 1998]
[DT1998]
CH=CH2
Br2
(i)NaNH 2 (3equi.)
(II)CH 3 I
Q.7
[IIT 2000]
CH,
CH 3 -C-CHBr
CH3
"
c H OH
2 5
>9
Q. 8
How would you synthesis 4 methoxyphenol from bromobenzene in NOT more thanfivesteps? State
clearly the reagents used in each step and show the structures of the intermediate compounds in your
synthetic scheme.
[IIT 2001]
Q.9
An alkene A (C16H16) on ozonolysis give only one product B (C8HgO). Compound B onreaction with
NaOH/I2 yields sodium benzoate. Compound B reacts with KOH/NT^NF^ yielding a hydrocarbon C
(CgHj Q). Write the structure of compound B and C. Based on this information two isomeric structures
can be prepared for alkene A. Write their structures and identify the isomer which on catalytic
hydrogenation (t^/Pd-C) gives a racemic mixture.
[IIT 2001]
Q.10
[IIT 2004]
CH2-C1
K C N
DMF
^Bansal
Classes
> / a\
( A )
(i)NaOEt/EtOH
r m
(ii)PhCHO/A
>
( B )
H3Oe
.
'
c(i)SOCl2 I
V^v (ii)CH3NH2
Halogen Derivatives
[24]
ANSWER KEY
EXERCISE-I
Q.l
Q.8
Q.15
Q.22
Q.29
Q. 36
Q.43
Q.50
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
D
B
C
C
B
A
A
B
Q.2
Q9
Q.16
Q.23
Q.30
Q.37
Q.44
A
C
B
D
C
C
B
Q.l
Q5
Q9
Q.13
Q.17
Q.21
Q.25
Q.27
Q.29
D
Q.2
A,C
Q.6
A,C,D
A,B,C, P
B,C,D
Q.10 B,D
A,C,D
Q.14 A,C,D
A,B
Q.18 A,B,C
A,C
Q.22 B,C
A
3, B
2 ,C
1,D > 2
A>2, B>!, C>4, D - 3
( A ) - Q ; ( B ) - S ; ( C ) - R; (D) - P
C
C
A
C
B
C
A
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
D
C
D
D
B
A
D
EXERCISE-I
Q.3
Q.7
Q.ll
Q.15
Q.19
Q.23
Q.26
Q.28
Q.30
(A)
Q.5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
A
C
C
B
C
B
B
Q6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
D
A
D
B
C
A
A
Q7
Q.14
Q.21
Q.28
Q.35
Q.42
Q 49
A
D
B
A
A
A
C
(B)
B,C
Q.4
A,B
B
Q.8
A,B,D
A,D
Q.12 A,C,D
B,D
Q.16 A,B,C,D
A,B
Q.20 A,B,C
A,B,C,D
Q.24 B,C,D
A -> 4, B
3,4, C - > 3, D -> 1,2
( A ) - S ; ( B ) - -Q; ( C ) - R ; ( D ) - P
(A)-Q;(B)-- R ; ( C ) - P ; ( D ) - Q
EXERCISE-II
Q.l
(i) CH 3 - CH - CH,,
OH
Q.4
(ii)
Q-5
(A)\TSJ
H
Me
Me
Me
I
I
I
(c) (A) Me - C = CH - Me, (B) Me-C-CH 2 -Me, (C) Me-C-CH 2 Me
OEt
(d)(A) n
1
Me
faBansal Classes
, (B) | 0 | ,(c) | O j
1
OTs
Me
Me
Br
Halogen Derivatives
[25]
Q.6
OH
OH
Et
(b) Ph-C-<^>
(c) Et-CH-Et
^CH2-CH2-OH
o
(e)
Q.7
(d)
Q.9
A=
Q.8
O L - C H - C H = CH9
Bs
C - C - C = C-C1
CH3
Conversion
(l)NaNH2
(a)AsEt-I
(b) B = CH3 - CH - OH
(c) Me2C=CH2
OH
(d) Me2C=CH2
C1CH2CH2CH2CN
(ii)
PhCHF2
(iii)
FCH2CH = CHC02Me
(iv)
Efl
(v)
no reaction
Q.13 (i) Chloroform responds carbylamine test while ethyl alcohol does not. Carbylamine test- The compound
is heated with aniline and alcoholic caustic potash-an obnoxious smell of phenyl isocyanide (C6H5NC)
is produced.
(ii)
Chlorine atoms of chloroform can be easily replaced by - OH group s on treatment with NaOH. Hence
chlorine atoms come in the form of sodium chloride. The solution thus when treated with silver nitrate
solution gives white precipitate of silver chloride. Chlorine atom in vinyl chloride is not readily replaced
by NaOH, hence it does not give precipiatet with AgN03 solution.
(iii)
The two compounds are hydrolysed with aqueous NaOH when 1,1 -dibromoethane form acetaldehyde
while 1,2-dibromoethane gives glycol.
(iv)
Chlorine atom in chlorobenzene is very less reactive, while chlorine in cyclohexyl chloride is very reactive.
Hence the two can be differentiated as above in (ii)
(v)
Apply test (ii) as above; when benzyl chloride gives white precipitate with AgN03 solution, while O
chlorotoluene does not give precipitate. Alternately, the compounds are oxidised when o chlorotoluene
give o-chlorobenzoic acid when benzyl chloride gives benzoic acid (having non chlorine.)
(vi)
n - Hexane does not respond CI" ion test even after fusion with Na and treatment with acidic AgN03.
the remaining three compounds are distinguished by their reactivity with alcoholic AgN03 solution.
^Bansal Classes
Halogen Derivatives
[26]
(a)
(b)
(c)
CH3 -CH=CHC1 (a
CH, = CHCHjCl (an
cHravcivci
H3C-CH-CH-CH3
CH3 CI
CH3
ch3
shydrogenated carbon.
faBansalClasse
Q.22 The strong -1. E offluorineatom in F3C - C < produces partial +ve charge on C atom of CF3 which
ultimately increases+ve charge on 2nd carbon atom to destabilize it
F
+5
i
F
In F3C+, the unshared pair of electrons in the p orbitals of each of thefluorineatom are shifted to C+ via
p-p orbital overlapping and thus stablizing F3C+ ion
Q.23 Dry gaseous hydro halogen acids are better electrophile. Also in aqueous solution F^O acting as nucleophile
may produce alcohol.
Q.24 KI reacts with RC1 to form RI. This RI molecule now hydrolysed easily to give ROH because alkyl
iodide are more reactive than alkyl chloride.
RC1 + KI - RI
H0H
Q.25 The more pronounced the nucleophilic activity ofthe attacking reagent, then the more the SN2mechasnism
will be favoured. Since in SN1 mechanism the raegent doesnot enter into the rate determining step of
ionisation How ever it can also be expected that as the nucleophilic activtiy is so slow that the mechanism
will changefromSN2 to SN1
Q.26 The dielectric constant of water is greater than that of aqueous acetone, and so ionisation of benzyl
chloride is facilitated.
Q.27 On movingfrom3 to 1 alcohol rate of ^ 2 reaction decreases and reaches to minimum and mechanesm
changesfromSN2 to SN1, Then rate of SN1 rate of reaction increases.
Q.28 Anhydrous A1C13 is used as a catalyst infriedelcrafts alkylation.
Q.29 tert-Butyl chloride, sec butyl chloride and CC14 with ale. silver nitrate
Me3C - CI >
">CHC1>CC1 4
c2H^
Br
Q.30
(a)As Q
-10
1=
C ^
CuLi
2
j]
D.
Q f
Hs
faBansal Classes
[28]
Me
Me
Pr, (B) Pr
H
Q.31
EtO
H
e
B e C10H21-C^CLi
A = CjqHjj-C^CH
D = C 1Q H 21 - C = C - (CH 2 ) 4 - CH - CH 3
C-C-C-C-C-C-Br
C
E e C1qH21 - C = C - ( C H 2 ) 4 - C H - C H .
H
CH
CH
CH
F-C10H21-C-C-(CH2)4-CH-CH3
H 0
Q.32
(ii)
(iii)
(iv)
(i)A,CH 3 CH 2 CH 2 Br;B, CH 3 CH = CH 2 ;
C, CH 3 CHBrCH 3 ;
D, CHgCHNE^CHg
A, CH 3 CH = CH^
B, CH 3 CHOHCH 3 ;
C, CH3CHC1CH3;
D, CH 3 CH 2 CH 2
A, CH 3 CHBrCH = CIi 2 ; B, CH2=CH-CH=CH2; C, CH 3 CHBrCH=CH 2 & CH 3 CH = C H - C ^ B r
A, CH 3 Clr^CHOHCH 3 ; B, CH 3 CH 2 CHBrCH 3 ; C, CH 3 CH = CH - CH 3
EXER
CISE-III
Br
Q.L
CH3-CH-CH2-CI
CH 3 - C = CH 2
CH.
(X)
CH3-C-CH
CH 3
2 - Bromo - 2 - methyl propane
(Z) (isomer of X)
Q.2
(Y)
Chloretone (Hypnotic)
Q.3
CH 3 CH 2 CH 2 CH 2 Br
CH 3 CH 2 CH = CH,
(A)
Br
(C)
(B)
CH 3 - CH2- C = CH
<P)
<!SBansal
Classes
Halogen
Derivatives
[29]
Q.4
(CH 3 ) 3 C - C =C"Na+
(CH 3 ) 3 C - C 3 CH
(A)
(CH3)3C-C = C H ^ ^ C T ^
(b)
(C)
OCH 3
Q.5
CH 3 - C(CH 3 ) - CH 2 - CH 2 NH 2
CH3-C(CH3)-CH2-CH2-Br
(B)
(A)
OCH 3
OCH 3
CH 3 - C(CH 3 ) - CH 2 CH 2 - OH
CH 3 - C(CH 3 ) - CH 2 CH 2 - NHCH 3
(D)
(C)
OCH,
CH3-CH-CH2-CH2-N-N = O
CH,
(E)
Q.6
(CH 3 ) 3 C - C ^ C L
Q.7
CH,
CH,
CH 3
C H 3 - C = CH
H 3 C C CH 3
Br
CH3-CH-CH2Br
(B)
(Q
CH,
(A)
CH,
CH 3 - CH - CH 2 CH 2 - CH - CH 3
(D)
Q.8
CH,
^CH,
C=C
"H
CH,
(A)
CH3 CH 2
Q.9
CH3X
CH^ CH2
CH 3 -COOH
C = CH - CH,
(B)
(A)
<!SBansal Classes
Halogen
Derivatives
CH,
(Q
;c = o
[30]
CI
Q.10 CH3- C = CH
CI
(A)
Q.ll
(B)
CH 3 -(CH 2 ) 3 C-C1
I
CH3
(C)
CH3(CH2)2CH = C(CH3)3
(A)
(B)
CH3.
Q.13
(CH3)2CH-CHCH2CH3
(CH3)2CH CH = CH CH3
(A)
(B)
.C2H5
^ C =C
(C)
Q.4
Q.ll
C
D
EXERCISE-IV
(A)
Q.5 A,B
Q.12 B
Q.6 B
Q.13 D
Q.7
(B)
Q.l
Q.2
Br
(ii) C6H5COOMgI + CH4
^Bansal Classes
Halogen Derivatives
[31]
ch3 ch3
Q.3
ch3
ch3
CI
HQ.4
-Ph
MeOPh
CH 3
Q.5
Q.6
(A)fQ
G=CCH3
C=CNa
,CH-CH 2 Br
CH-J
NaNH,(liq.)
*(B)
CH,
Q.7
CH 3 -C-CH 2 CH 3
oc2h5
ONa
Br
OMe
I C 3 J A high pressure^ [ o )
MejSO^ [ o ]
'
OMe
OMe
OMe
NaOH
conc.H,SOd
NaOH
SO,H
-Co)-
->(0)
ONa
OH
OMe
OMe
Alternative rout
Br
Br
Br
Br
naoh
o j - ^ ^ i o j
> [ q j ^ l o j - . .
OMe
ONa
SOiH
n a o h
> [ o j - ^ l q .
OH
ONa
Q.9
(A) PhC(Me)=C(Me)Ph
KOH
KU
NH3-NH3
CN
Q.10 (A)
mBansal Classes
COOH
CONHCH,
!
CH = C
(D)[OJLOj
Halogen Derivatives
[32]
Q.13
Q.14
->is:
Br
Br
(A)
Br
(C)
(D)
Me
f5
Me
HO|H
Me
H|CI
11
Et
-OH
-> H1
Et
B
Steps I and II are
(A) both SN1
Br
Et
A
(B) both SN2
.
J\.
(i)CH3CHO ^
f Jj
(ii)aq.NH4Cl
.^-Br
CHOHCH3
MgCl
(A)
Br
CI
*{S
V
MgCl
CI
(B)
MgBr
^-Br
&
CHOHCHi
MgCl
(C)f|
&
Br
^-CHOHCH3
H,0 +
> C4H10O
(alcohol)
(B)
Alcohol B reacts fastest with Lucas reagent. Hence A and B are
O
II
II
(C) C H 3 - C - 0 - C 2 H 5 , ( C H 3 ) 2 C H 0 H
faBansal Classes
NOMENCLATURE
(D) H - C - O - C 3 H 7 , ( C H 3 ) 3 C O H
OFORGANIC
COMPOUND
[3]
Mg
CI
ET,0
Qc
MgCi
(B)
(A)
\JX*
CI
MgBr
H
i
^CH3
H,C'
(A) SE2
1
B r
(B) SN1
V~V
.(CH2)5CH3
HO-C
X-Br
V^
(Q
C H 3
(D) SN2
(C) SN
OH-
H A _ A H
Ais:
HOV
,CH 3
h/LAH
(C) Both
(B)
(A)
H\/
\/
oh/V_AH
(D) None
CHCI3 + OH HCOO"
Intermediates ofthis reaction are
(A) :cci:
J&
(B) :CCL
(C) both
(D) None
(D)BothA&B
)CI
(B) ( O V - C I
(C) ( O / ~ c h 2 c i
The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(A) Alkyl chlorides are immscible with SOCl2
(B) The other products of the reaction are gaseous and escape out
(C) Alcohol and SOCI2 are soluble in water
(D) The reaction does not occurs via intermediate formation of an alkyl chloro sulphite
<!Bansal
Classes
Halogen Derivatives
[194]
CH,
Q.34
H-
H_
CH
c H O-
Br
> ? Major product is:
C2H5OH
h3Cx
/H
(A)
H3Cx
(C)
H3Cv
/CH 3
(B)
IK
<!Bansal Classes
^ch3
^D
>
H3Cx
(D)
Halogen Derivatives
<
^H
C = C
X
\
CH3
[5]
Q35
(A)
Q.36
u O
H - A CH 3
BRH
(A)
Q.39
(B)
LaJ
(B)
(D),
(C)
E2
JJ
S ) E ^ ^ n e 0 S 8 e n e ^EAylcWoTde
CH3 - C - CH3 - i s
il
tij
> (A)
Agp<nvder
> (B)
H s0
(A)]
(C)]
Q.40
(D)]
^r^Trrtiztir
Q.41
042
( A ) Q
CB)|)
( C ) ^
.(D) I
Q. 43 The appropriate naming for the second step in the haloform reaction is:
(A) Halogenation
(B) Dehydrohalogenation
(C) Reduction
(D) Dehydrogenation
Q. 44 Which product is obtained when bleaching powder is distilled with acetone:
(A) CC14
(B) CHClg
(C) CH2C12
(D) CH3C1
Q.45 What will be the reduction product of following reactions:
+2H
Zn/HCl (ale)
CHCI3-
+4H
Zn/HCJ (aq.)
+6H
Zn/H 2 0
(C) CHoCl
(D)CHC13
is converted into
/^Y3
I
by:
(A) (i) CH3~ Mgl, H30+ (ii) H2S04, A, (lii) HBr, R202
(B) (i) CH3- Mgl, H30+ (ii) H2S04, A, (iii) HBr
(C) (i) CH3-MgI, H30+ (ii) HBr
(D) (i) HBr, R ^ (ii) CH3-MgI, H30+
Q. 49 To form Malonic acid, by shortest possible route, we have to start a reaction from:
(A) Ethyledine chloride (B) Methyl chloride (C) Methylene chloride (D) Chloro ethan
Q. 5 0 Frankland reagent is:
(A) Dialkyl lithium
(B) Dialkyl Zinc
<!Bansal
Classes
Halogen Derivatives
[197]
EXERCISE-I
(B)
(Choose the correct option. One or more than one are correct)
Q.l
[X]is:
H
Br
(A)kXJ
(B)rN
(C)
(D)
Br
Br
Q.2
Q.3
A solution of (R)-2-iodobutane, [a] = -15.9 in acetone is treated with radioactive iodied, until 1.0% of
iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be
15.58, which statement is correct about above information.
(A) It has optical purity 96%
(B) % of R in solution is 99%
(C) Racemic mixture is 2%
(D) Final solution is dextrorotatory
Q. 4
. A
moistAg,U
2
>
CH 2 OH
CH,
CH 2 OH
Xchoh <&< 1
CH
(C)C >
(D)
OH
Q.5
t B
Br
(C)
&/
CH 3 CH 2 -CH-N
CH,
faBansal Classes
CH C
(B) CH 3 CH 2 - CH - CH 3
3 ^OK >
Br
CH 3
CH 3
oh
>
CH,
NOMENCLATURE
(D) CH CH C H - C H
S
011
>
S(CH3V
OFORGANIC
COMPOUND
[8]
Q.6
(i)Et2
A+B
> Alcohol
H2Cr 4
> Ketone
CH
(D) Ais isopropyl magnesium iodide
(C)Bis CH3-CHCOCI
H
CH
Q.7
I
H
CH3
CH 3
(A) C H 3 - C H - C H 2 B r
(C) CH3CH2CH2Br
Q. 8
(D) C H 3 - C H - C H33
Q. 9
^Bansal Classes
Halogen Derivatives
(D)R-Br
[9]
H-C-OTS
NaCN
CH3CH2CH-CN
Benzoyl chloride is less reactive than acetyl chloride for nucleophilic acyl substitution reaction because
0
(A) - C - group ofbenzoyl chloride is in conjugation with benzene ring. This makes benzoyl chloride
more stable than acylchloride.
(B) CH3- group of acetyl chloride make C-Cl bond stronger due to the +1 effect.
(C) C6H5- group ofbenzoyl chloride make C-Cl bond weaker due to +R effect.
(D) Carbonyl carbon in benzoyl chloride is less electron deficient than acetyl chloride
(C)3
(B)5
(A)L
(D)4
(B) CH3CH2CH-CH3
CI
II
s
<!Bansal
Classes
CH3
Halogen Derivatives
[10]
(C) C H 3 - C H - C = O
Br
le0
(A)
CMe3
(B)
CMe,
CMe,
<P)
(C)
Br
Q.18 3-Phenyl-3-pentanol can be prepared from grignard reagent & other component which can be
(A) 3 -pentanone
(B) Ethylbenzoate
(C) Ethyl phenyl ketone (D) Propanoyl chloride
Q.19 In which of following reaction inverted product will obtained.
(A) SN1
(B)Sn2
(QSnNgp
(D)V
<!Bansal
Br
Br
(A)
(B)
Classes
(C)
0>
Halogen Derivatives
Br
"0
[11]
Q.21
Q.22
Q.23
Q.24
(D) H ^ C H - C I V C L
(C) Ph-Cl
(B)
CH 3 CI
NaOI
(D) Ph - C H - CH - CH 3
(Q
yellnw solid
G can be
(B) C H 3 - C - C H 2 - C " C H 3
(A)CH3-C-OCH3
II
O
(D)
(C) CD3COH
CCH3
o
Q.25
Match the List I (reaction) withList II (reaction intermediate) and select the correct answer using the
codes given below the Lists.
Listn
List I
(A) CF3-CHC12
alc.KOH/A
>
CF2 = CC12
(1)
Transition state
(2)
Carbocation
(3)
Carbanion
(4)
Free radical
CH3
(B) CH3 - C - OH
CH,
(C) CH3-CH2-Br
> CH 2 -CH 2
Br
(D) C H 3 - C - C H 3
CH,
^Bansal Classes
aq.KOH/A
>
CH,
Halogen Derivatives
P2J
Q.26
Match the List I with List II and select the correct answer using the codes given below the Lists.
List I
Listn
(A)E1CB
(1)
Quaternery Amine oxide
(B) Saytzeff alkene as major product
(2)
Xanthate
CI
Q.27
(C)E2
(3)
CH3-CH2-CH-CH3
(D)E C
(4)
C6H5-CH2-CH-CH3
Match List I with List II and select the correct answer from the codes given below:
ListI
List II
(A)
CH 3 -O-SO 2 CH 3 + C 2 H 5 O
(1)
CH3CI^P H 2
(B)
CH 3 -CH2-I + PH 3
(2)
CH 3 -O-C 2 H 5
Q.28
(C)
HC = CNa + CH 3 -CH2-Br
(3)
CH 3 -O-CH 3
(D)
CH 3 -CI + CH 3 -O
(4)
CH=C-CH 2 -CH 3
Match List-I with List-II for given S n 2 reaction & select the correct answer from the codes given below
Z-CHJBR + CH 3 0
List-n
(P)0.1
List-I
(A)H(B) CH 3 (C)C 2 H S -
(0)3
(R)l
CH 3
(D)
\
CH
Q.29
Z-CH 2 -OCH 3 + Br
iftcdl'i
CH
(S)100
(C) R - M g X + C 0 2
n-carbon
(P) Ketone
Adduct
Adduct
faBansal Classes
H,O
> Adduct
(B)R-MgX + (CH2) 2 0
n-carbon
List-n
H3
Adduct
>
>
3 >
Halogen Derivatives
[13]
Q.30
List-n
List-I
/OCH
W-
-C>
(A)
CH,CH 2 Q
CH,0
CH,0
>
(P)E1
CH3O
0
II
c
CB)
CH
CH22CH2Br
W
33
CH 3 CH 2 O
(Q)E2
CH,CH,OD
(R)Elcb
(C)
Br
CD)
feBansal Classes
Br
ale. KOH
(S)Ec
Halogen Derivatives
[14]
EXERCISE-II
Q.l
(i)
(ii)
(iii)
(iv)
(a)
(b)
(v)
Although ethers are weakly polar, are used as solvent of choice for Grignard reagents.
(vii)
Treatment of either CH3-CH - CH-CHjBr or CH3-CH -CH - CH2 with aqueous HO~ gives the
O
same product. Also write down mechanism involved, & IUPAC name of product.
Q.2
(a)
(b)
(c)
(d)
(e)
On reaction between an alkyl halide and KOH in a mixture of water and ethanol, compare the two
mechanisms SNj and SN2:
relative rates of CH3X,C2H5X,iso-C3H7X&tert-C4H9X
relative rates for RC1, RBr and RI
effect on rate of a rise in temperature
effect on rate of increasing water content of the solvent.
effect on rate increasing alcohol content of the solvent.
Q.3
In the following reaction is carried out in the weakly ionizing solvent, acetone (CH3)2C=0. (Bsisbrosyl,
p-bromo benzene sulfonyl)
n-C4H9OBs + X >n-C4H9X + BsOThe order of reactivity of halide ions depends or the salt used on their source :
+
ifLi X~ isused,I^r-^Clif (n-C4H))4N+ X - is used C l - > B r - > I ~
How do you account for this contrast in behavior ?
Q.4
Which of the following is the correct method for synthesizing 4,4-dimethyl-pent-2-yne, using sodamide
in liquid NH3? Given reasons.
CH3
(i) CH3C=CH + CH3 - C - Br
CH3
>
CH3
Q.5
(a)
CH3
faBansal Classes
Halogen Derivatives
[15]
C2H5O
CH3
(b)
C 2 H 5 OH
CH3-C-CH2-Br
CH3
H
(C)
Nal
TsCl v *
A
Pyridine
NaBr
CH, OH
Q.6
(a)
H3 +
> A
O
MgCl
(b)
Ph-OCl +
(2 eq)
(c)
H - C -OEt + CHgCHjMgBr
h3o+
(2 eq)
(d) QCMgI +
(1 eq.)
CH2
HCl
(e)
H3C
> E
Ph
C2H5
Q.7
(a)
OH
<J)MgBr + (C2H5)2CO
(b)
C2H5MgBr +
^>C =0
H
(c)
H,0
C2HsMgBr + <j>-COOCH3
<!SBansal
>
5C2
Classes
z >
Halogen Derivatives
[16]
(d)
H2
<f>MgBr + C2H5COOCH3
>
I
H
Ci
Q9
Zn
.
Zndust' A n
I
CH3-CH-CH-C
CH
H 2, -- C
C 1I
--
convert?
CH3
Q.10
(a)
(b)
(c)
(d)
What is/are the limitation in the formation of Grignard reagent by RX+Mg dryether >
R should not contain any acidic group
R should not contain any electronegative group
Alkyl halide should not be vicinal dihalide
Alkyl halide can't be Tertiary.
Q.ll
(a)
CH^jCHjCl + 1 ~ - A
(b)
(c)
(d)
CH 3 -CH-CH 2 -OH
Conc NaUH
) E,
C l C ^ O ^ C H ^ r + KCN
(ii)
PhCHO
Oii)
BrCH2CH = CHC0 2 Me
(iv)
(v)
EtOH + HI
>D
EtOH + HCN
>E
>A
SF
* >B
^
>C
Q.13
C 2 H J O H f r o m CHC1 3
(ii)
(iii)
(iv)
(v)
(vi)
<!SBansal
Classes
Halogen Derivatives
[17]
[ > CH? - OH
^ q)Li a ^
(ii) CuF
+B
- ^ A - ^ B
J.IMID4
NBS
1 C
ale.KOH.
CH,
(b)
OH
CH3CH2CH2
H
(i)TsCl
kii)C2HsO"K+
(A)
Hi) K
kii)C2H5OTs
(B)
[18]
[ORGANIC CHEMISTRY
XII (ALL)
HYDROCARBON
GMP
(1)
H2,Ni
R-OCH
200~300C
or
R-CHCH,
Sabatier senderen^
reaction
(1)
X , , hv or UV light or 400 C
(2)
Nitration
Z n - C u + HCl
(2)
R-X
(3)
R-Mg-X
(3)
RedP-Hi,LiAlH4
(5)
(6)
R-N
Sulphonation H 2 S 2 0 7
+HOHorROH
+
S 0
orNH3 orRNH2
(4)
RX
Reed reaction^
G 1
2
R S Q
hv
RX
Wurtz reaction
A1CL/HC1
Zn
RX
Isomerisation
Frankland's reaction|
R - C - C l or ROH
Pyrolysis
RedP/Hi
0
or
R-C-R
Cr or Mo or V oxide
or
(7)
RCHO
+ A1 2 0 3 500C
R-C-R
(7)
R-C = O
(8)
(8)
step up reaction
Higher alkane
Z n - H g / C o n e . HCl
Clemension's reduction
CO. + H0
H 2 N-NH 2
Wolf / Kishner reductiori
Combustion
or
(RCH2CH2)3B
(9)
(10)
RCOONa
NaOH+CaO
RCOONa
feBansal Classes
HYDROCARBON
[2]
GMP
(1)
R-CH-CH-OH
(2)
R-CH-CH-X
GR
conc.H 2 S0 4
-H.,0
-HX
R-CH-CH<*
R - C H - C H .
(4)
X
(5) R - C
(6)
(7)
^
Ni,H,
^ ^ COOK
RCH-COOK
>R-CH-CH
200-300C
(3)
HX
R-CHX-CH3
>
(4)
HBr, Peroxide
(5)
HOCl
R-C-O-CH2-CH2-R
(7)
R - C H ( O H ) - C H CI
>
+ H 0
I/2Q 2
Pyrolysis
R-H
(10) C H =CHC1
R-CH2(0H)-CH3
.R-CH-CH?
Ag300C
O
R-CH-CH9
(8)
(10)
Pyrolysis
R - C H - C H Br
dil.H 7 S0 4
(6)
(9)
(C2H5)4N+OH
^R-CHX-CH2X
200-300C
O
(9)
R-CH=CH,
or
Cn H,2n
X
CH
H, Ni
(2)
ale. KOH
Zn dust
(3)
(1)
+ch
2N2
CHO
_J5^(RCH
CH
(11)
(12)
0 CS ov 4
-CH-CH3
CO
+H2
)
CO+H-,
HCO(CO)4>
o.
RD
CHO
R - C H - C H ,
OH
Bayer reagent
=
OH
R - CH 7
1 % alkalineKMnO.
CH,
strong oxidant
OH
(14)
>CO2 + H2O
CuR.
(13)
R - C H .2 - C H
+
'CHO
OH
OH
jj
o
Per acid
(15)
R-CH-CH2
o,+H,0
(16)
(17)
(18)
(19)
(20)
(21)
faBansal
Classes
Ozonolysis
200ChighP
Cl2
>
500C
Polyalkene
C^H
O
Substitution product
A1 2 (SQ 4 ) 3
200-300C
Isomerisation
acetic anhydride
R-CH =CH-COCH
;
t
2
3
ALKANE
HYDROCARBON
1) CH2Br-CH2Br
2) CH3-CHBr2
(1)
alc.KOH,NaNH2
(3)
4) CHBr-CHBr;
C2H2
Zn dust
(5)
Zn
CHBr
6) CH=CH-C1
7)
H,0
9) 2C + H2
(8)
N
(9)
HC-COONa
8) CaC2
(6)
(7)
alc.KOH,NaNH0
4 '
HBr
>CH,BrCH,Br
J
Peroxide
(4)
CHBr
5)
(2)
Ag powder
3) CHC13
Ni
'
HBr
[NoPeroxide
CH3-CHBr,
Hoci y, CI CHCHO
HCN jB a(CN) 2
CH,=CHCN
^CH3CH(OCOCH3)2
CH3COOH,Hg'T
-> CHCHO
(Kucherov's reaction)
.CH,CH(HSO,)2
Cone.H,SO,
AsCl,
10) CH3-CSCH
(i)Na (ii)R-X
10) CH-CsCH
(i)CH3Mg!(ii)R-X
(11)
>
HgS0 4
CO+HOH
(12)
(13)
CH?CHO
' CH =CH-COOH
Ni(CO) 4
CO + EtOH
Ni,160C
* CH=CH-COOEt
(14)
NaNH,
(15)
AgNO, +N114OH
,
,
(Tollen snRe agent)
.Na-CsC-Na
* Ag-CsC-Ag
b
Cu-C=C-Cu
2 + H,0
(16)
(17)
Combustion O2_C0
(18)
Bayer Re agent
CU 2 CI 2+ NH 4 OH
CHO
-> H C O O H
CHO
(19)
> H-C-C-H
I '
o o
Trimerisation
HCOOH
+H2Q
Ozonolysis
Trimerisation
(22)
Dimerisation
(23)
(24)
^Bansal
Classes
[Ni(CN) 2 ]
[Cu(NH3 ) 2 ] +
"^butenyne
CH-CH
II II
CH-CH
S
CH,OH
3
)
(BF 3 -HgO)
HYDROCARBON
CH(OCH3)2
CH-,
methylal
[41
EXERCISE-I
Q. 1
The reaction of E-2-butene with CH212 and Zn-Cu Couple in either medium leads to formation of
CH
(A)
Q. 2
(A)
CH,
H>
CH,
CH,
(B)
H/\
/\CH3
(C)
c n , y
yci-i?
(D)
CH3/
(C)
(A)
CI
Q3
Q. 4
(a)
Q. 5
(b>
GC
(c
CC
(d)
(x)L
(z)
(y)l
Q. 6
(D) 2,4-hexadiene
11
Me
DU
gQ
-> P reaction is
Me
p h
V _ /
C H 3
V
H,C
(C)
'/'C
HYDROCARBON
[5]
+Br2
Q 7
mixture of product. Among the following which product will formed minimum
amount.
Br
(B) \
Br
(A)
Q.8
H 2
ft
(C)
- M ^ P ( M a j o r ) -
(Major)
The structure of Q is
Br
Br
Br
(C)
(B)
(A)
CH3
Q9
Br
(D)
IS
[f
(i)CH,COOOH
hACH3-^^
CH,
"OH
-OH
(A)
Ph1 0
H,C-
(C)
CH,
CH,
-OH
-H
H"
(B)HO-
18
-CH3
-Ph
A"
* P(Alkene)
CH,
-OH
CH,
-OH
-OH
-OH
Br, .
Nal
Acetone
c h
CH,
CH,
CC1,
18
Q (Alkene)
OCOR
(A) Both
Phx
//CH3
yPh
(C) B o t h Ph-CH C^
Q.ll
(D) Both
faBan sal
Classes
CH,
l3
CH 2
CH3\
Ph
H,C
Ph
Me
/CH3
Ph
Ph
Ph
CH 3
Ph
HYDROCARBON
[6]
Q. 12
CH. - C = O
(Q
CH3-C = O
(B)
C H 3
_I
= 0 &
CH
-O-CHO
CH3-C = O
CHO
&
CH3-C = O
CHO
& CH3-C-CHO
(A) |
CHO
( D )
CHO
CH3-C = 0 '
C H
3 "
CHO
0 _ C H 0 &
CHO
COOCH,
0 S 0 4 (leg)
Q.13
-COOCH3
H 2 0/ Acetone
X.
Identify'X'.
COOCH,
,COOCH 3
OH
(A)
(B) OH
OH
COOCH,
COOCH,
COOCH3
OH
OH
COOCH,
HO
(C)
OH
HO
PdCL.HOH
OC2H5
Q.14
CuCi,,0,
^z.
OC2H5
OC 2 H 5
OC 2 H 5
0
CH, CH,
Q.15
'
CH, - C = C - CH 0 - CH = C H ,
CH3CH3
OH
0s04(lequiv.)
(Acetone/water)
A; Identify A
CH 3 CH 3
OH
(A) CH 3 - C = C - C H , - CH - CH 2
(B) CH 3 - C C - CH 2 - CH = CH,
I
OH
CH,
I
CH,
I
(C) C H 3 - C H C
I
OH
l & B a n s a l Classes
OH
CH 2 - C H - CH 3
OH
HYDROCARBON
[215]
Q, 16
(A)S[
Q.17
equi.)
+ CH 2 N 2 (1
Pb
(QAc)2
(B) I
)B;
identify B
(C)L/J
(D)
(B) CH3 - CH - CH = C - CH 2 CH 2 CH 3
CH3 CH3
(C) CH3CH - C
CH3
C - CH3
CH3
Q.19
CH3
CH 3
CH3
(D) CH 3 CH 2 CH 2 - C = CH 2
CH3
CH3
Br
Q.20
f^Jf^
alcoholic KOH
product
o
Q.21
( b ) o f
( c )
0 -
( d )
0 -
Number of required 0 2 mole for complete combustion of one mole of prop ane (A) 7
(B) 5
(C) 16
(D) 10
faBansal Classes
Q. 22 How much volume of air will be needed for complete combustion of 10 lit. of ethane (A) 135 lit.
(B) 35 lit.
(C) 175 lit.
(D) 205 lit.
Q.23
When n-butane is heated in the presence of A!Ci3/HCl it will be converted into (A) Ethane
(B) Propane
(C) Butene
(D) Isobutane
Q.24
(C) OK"
(D) RO
Q.25
The product of reaction between one mole of acetylene and two mole ofHCHO in the presence of
Cu2Cl2 (A) HOCH, - C = C - CH2OH
(B) H2C = CH - C s C - CH2OH
(C) HC = C - CH2OH
(D) None ofthese
Q.26
PMA polymer is formed by methyl acrylate, which is prepared as follows (A) R - C = CH _coB!L_>
( B ) HC 3 CH -
(C) HC = CH
'
Ni (CO ) 4
C +CH3 H
Ni(CO)4
>
Q.27
During the preparation of ethane by Kolbe's electrolytic method using inert electrodes the pH of the
electrolyte (A) Increases progressively as the reaction proceeds
(B) Decreases progressively as the reaction proceeds
(C) Remains constant throughout the reaction
(D) May decrease of the the concentration of the electrolyte is not very high
Q.28
Ethylene forms ethylene chlorohvdrin by the action of (A) Dry HCl gas
(B) Diy chlorine gas
(C) Solution of chlorine gas in water
(D) Dilute hydrochloric acid
Q.29
(D) Pent-2-ene
Q.30
Which alkene on heating with alkaline KMn04 solution gives acetone and a gas, which turns lime water
milky(A) 2-Methyl-2-butene
(B) Isobutylene
(C) 1-Butene
(D) 2-Butene
Q.31
Acetylene may be prepared using Kolbe's electrolytic method employing (A) Pot. acetate
(B) Pot. succinate
(C) Pot. fiimarate
(D) None of these
Q.32
<
Imflar
R-QC-R
Na/NH3
> A
HYDROCARBON
[9]
Q.35
An alkyne C 7 H 12 on reaction with alk. KMn0 4 and subsequent acidification with HCl yields a mixture
CH3-CHCOOH
of
+ C H , C H 2 C 0 0 H The alkyne is -
(A) 3-Hexyne
(C) 2-Methyl-2-hexyne
(B) 2~Methyl-3-hexyne
(D) 2-Methyl-2-hexene
Q. 3 6
A compound (C5Hg) reacts with ammonical AgN0 3 to give a white precipitate and reacts with excess of
KMn0 4 solution to give (CH 3 ) 2 CH-COOH. The compound is (A) CH 2 =H-CH=CH-CH 3 '
(B)(CH 3 ) 2 CH-CsCH
(C) CH 3 (CH 2 ) 2 C=CH
(D) (CH 3 ) 2 C=C=CH 2
Q. 3 7
Which ofthe following reagents cannot be used to locate the position of triple bona in CH 3 -C=C"CH 3
(A) Br2
(C) Cu 2 +
(B)03
(D) KMn0 4
Q.38
CH 3 -CH 2 -C=CH c
CH 3 C=C-CH 3
(C)
Q.40
B <
(B)Both^)x-CH3
C Hj OH, Q - C H ,
BH3
F
H2O2 OH"
CH3-CS;CH
(D) Q - C H ,
HgSo 4 /H 2 so 4
Q-CH3OH
A and B a r e O
II
II
(A) C H 3 C H 2 C H O , C H 3 - C - C H 3
(B) C H 3 - C - C H 3 C H 3 C H 2 C H O
(D) CH 3 - C - CH 3 (both)
o
HYDROCARBON
[10]
NaBD,
0 41
CH3CH=CH2
product X
Xis(A) CH 3 - CH - CH 2 D
(B) CH 3 - C H - C H 2 0 H
OH
(C) CH 3 - CH - CH 3
OD
Q. 42
CH 2 =CH-CH=CH 2
cc
(B) CH 2 = CH - CH - CH 2 - CC13
Br
(C) CH 2 = CH - CH - CH 2 - Br
CC13
Q.43
Mixture of one mole each of ethene and propyne on reaction with Na will form H 2 gas at S.T.P. (A) 22.4 L
(B) 11.2 L
(C)33.6L
(D) 44.8 L
Q.44
(A)
II
(B)
CH 3
CH 3
O
(C)
None of these
HYDROCARBON
[219]
NH4C1
Q.45
CH^CH
>
product
CH 3
Q. 46
(D) Cu-C^C-NH 4
CH 3
CH 3 - C = GH - C - CH 3
CH 3
O
il
II
Q.47
Alkene A
/H
2 )
A can be C(CH 3 ) 2
CHCH,
( A ) CH 3 -C-CH=C:
,CH3
I!
(B) CH 3 - C - CH = HC - CH 3
^CH,
Q.48
HO
reagent R,
OH
HO
OH
CH.
Q.49
H-C
II
HC
CH 3
(A) A is meso 1,2-butan-di-ol formed by syn addition
(B) A is meso 1, 2-butan-di-ol formed by anti addition
(C) A is a racemic mixture of d and /, 1,2-butan-di-ol formed by anti addition
(D) A is a racemic mixture of d and 11,2-butan-di-ol formed by syn addition
l&Bansal Classes
HYDROCARBON
[12]
Q.50
H30+
/O + C H : M g B r
^A
Con.H2S04
>
Q 3 /H 2 0/Zn
r.
A, B and C are A
HO
CH,
(A)
"HO
HO
CH,
CH 3
(B)
IHCHO
HO
(C)
CH,
CHj
HQ.
jCH,
CH,
i
CH,
g
CH,
(D)
Q S 1
OOH
'
(C)Et 3 N
(D)t-BuOK
BrCH 2 -CH 2 -CH 2 Br reacts with Na in the presence of ether at 100 C to produce C H 2 - CH2
(C) \
\
3
CH,3
(l)Hg(0Ac)2/H20/THF
(2)NaBH4 NaOH Ii 2 0
CH,
(A)/
( B ) y = y
n_ro
3OH
/
(E)
I
(B)C
(C
A.AlSOH
4-CH,
rr-OH
3\
( D ) ^ > =
(C)
HYDROCARBON
rr-CH,
(D)
[13]
Q. 55
An organic compound ofmolecular formula C4H6, (A), forms precipitates with ammoniacal silver nitrate
and ammoniacal cuprous chloride.' A' has an isomer 'B', one mol ofwhich reacts with one mol ofBr2 to
form 1,4-dibromo-2-butene. Another isomer ofA is ' C \ one mole of C reacts with only 1 mol. of Br,
to give vicinal dibromide. A, B & C are
(A) CH 3 -CH 2 -OCH and CH 2 =CH-CH=CH 2 ; f j |
(B) CH 3 -C=C-CH 3 and CH 3 -CH=C=CH 2 ; CH 3 -C=C-CH 3
CH2-CH
CH9\
(C) I ~ . O C H , and
; CH2 = CH-CH=CH 2
CH2-CH
CH,/
(D) C H 3 - C S C - C H 3 and C H 2
-CH.
|
CH2
; CH 2 = C H - C H = C H 2
^CH^
Q.56
Q. 5 7
CH 3 -CH=CH-CH 3
product is Y (non-resolvable) then X can be cis
(B) H C 0 3 H
(A) Br2 water
(D) all of the above
(C) Cold alkaline KMn0 4
Electrophilic addition reaction is not shown by
(A) CH2 = C - CH3 and Br2
CH 3
(C) CH 3 -CsCH and CH3MgBr
Q. 5 8
A mixture of CH4, C 2 H 4 and C 2 H 4 gaseous are passed through a Wolf bottle containing ammonical
cuprous chloride. The gas coming out is
(A) Methane
(B) Acetylene
(C) Mixture of methane and ethylene
(D) original mixture
Q. 5 9
In the presence of strong bases, triple bonds will migrate within carbon skeletons by the
(A) removal of protons
(B) addition of protons
(C) removal and readdition of protons
(D) addition and removal of protons.
Q.60
CH 2 =CH-CH=CH 2 +
CHCOOH
CHCOOH
COOH
COOH
Diels Alder
COOH
y^yCOOR
( Q l O i .
fa Ban sal
COOH
Diels Alder
Friedel-Crafts
(D)
COOH
COOH
Classes
Friedel-Crafts
COOH
HYDROCARBON
[14]
Q. 61
For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of
reactivity as measured by reaction rates:
(I)C1CH=CH2
(1I)(CH3)2.C=CH2
(in) OHC GH=CH2 ^V)<NC)2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C)III>II>IV>I
(D) II > I > III > IV
Q. 62
Q. 63
dibromo
CH3-C-NH2
/ > ~ B r - Mg/drycther^pQ
Q.64
^(Y)
V-MgBr
(C)X= < ^ ^ M g B r
(D) X - BrMg
faBansal
Classes
MgBr
Y=<
Y=
Y = HO-
HYDROCARBON
VoH
OH
115]
EXERCISE-I (B)
Q.l
HgS04/H2SQ4 ^
BH,/THF
H 2 O 2 /OH
(D)
(Q
Q.2
An alkene on ozonolysis yields only ethanal. There is an isomer of this which on ozonoly sis yields:
(A) propanone
(B) ethanal
(C)methanal
(D) only propanal
Q.3
CH 3 - CH = CH-CH, + CH 2 N 2 ~ > A
A can be
(A)
Q.4
(C)
Reagent R,
Re agent R2
Q.5
HO
HO
OH
R, and R 2 are:
(A) cold alkaline KMn0 4 , 0 s 0 4 / H 2 0 2
(B) 0 s 0 4 / N a H S 0 3 ; A g 0 2 , H 3 0
(C) cold alkaline KMn0 4 , C 6 H 5 C 0 3 H / H 3 0 (D) C 6 H 5 C 0 3 H ; 0 s 0 4 / NaHS0 3
Q.6
H2/Pt
(A) C 4 H 6
> (B) C 4 H g
-> CH 3 COOH
Hence A and B are
(A) CH 3 C = CCH 3 , CH 3 CH = CHCH 3
(B) CH 2 = CHCH 3 = CH 2 , CH 3 CH = CHCH 3
CH 3 CH = CHCH 3
(C)
Q. 7
Q.8
(D) None
(B) CaC 2 + H 2 0
> C2H2
(D) Me 3 C-H + a q . K O H ^ M e 3 C - O H
Ph-CH 2 -CH 3
A could be:
(A) NH 2 NH 2 , glycol/OH
(C) P/HI
(D) CH 2 - CH 2 ; Raney Ni - H ^
SH
HYDROCARBON
SH
[16]
Q.9
BuOK
>Product
-CH,
CH,
CH,
(C)
(D)
Q.10
C V
NBS
> A, A can be
(B) CH2=CHCH=CH-CH2Br
Br
(C) CH2 = CH CH2 CH = CHBr
Q.ll
Q.12
Ph-CH-CH 2 + BrCCl,
P^oxide
Product is:
H
H
(A) Ph-
-CH2CC13
- CH?Br
(B) Ph-
Br
CCI3
Br
CCI3
(C) Ph-
CH2CC13
(D) Ph-
CH2Br
HYDROCARBON
[17]
Q.13
Which of the following elimination reactions will occur to give but-1 -ene as the major product?
(A)
CH3.CHCl.CH2.CH3 + KOH
(B)
CHvCH,.CH.CH,+NaOEt
EtOH
NMe3
(C)
(D)
CH3.CH2.CHC1.CH3 + Me3CoK
CH3.CH2.CH(OH).CH3 + conc.H 2 S0 4
The above compound undergoes ready elimination on heating to yield which ofthe following products?
(A) O Cx h ,
Me-^
Me "
<B) O
Me^ ^Me
(C)
Me^ ^Me
(D)
Me^
^Me
Q.15
Which of the following will give same product with HBr in presence or absence of peroxide.
(A) Cyclohexene
(B) 1-methylcyclohexene
(C) 1,2-dimethylcyclohexene
(D) 1-butene
Q.16
The ionic addition of HCl to which of the following compounds will produces a compound having CI on
carbon next to terminal.
(A)CF3.(CH2)3.CH=CH2
(B)CH3.CH=CH2
(C) CF 3 .CHCH 2
(D) CH3.CH2CH=CH,.CH3
Q.17
Q.18
Which reagent is the most useful for distinguishing compound Ifromthe rest ofthe compounds
CH 3 CH 2 CSCH
CH 3 CSCCH 3
CH3CH2CH2CH3
CH3CH=CH2
1
(A) alk. KMn04
n
(B)Br2/CCl4
m
(C) Br2/CH3COOH
iv
(D) AmmonicalAgN03
faBansal Classes
HYDROCARBON
[18]
(B) HCsCH+CH^
> O^Cl-CHCl-CHG
HC^X
> II
N
HC
1-1
photo
haiogenation
(D) CHJ-C^C-CHJ-C^-CHJ
Q.23
J><CH2_CH2_CH3
List I
(A) n-Hexane
List II
Cr203-Ai203,A ^
(B) CH s CH
RedhotFetube
>
CH3
(C)CH3-C- X
I
CH3
> aq.
(3)Aromatisation
(D) CH3-CH2-X
(4) Cyclization
faBansal Classes
HYDROCARBON
[19]
Q.24
List I
List n
(I)B
% )
(1) CH 3 -CH2-CH=CH2
(ii)H 2 0 2 /0H
CH 3
^QAVHOH)
(B) CH 3 - C = CH 2
(2) CH 3 -CH=CH-CH 3
(ii)NaBH4
CHQ
CI
(C) CH 3 - CH 2 - CH - CH 3
CHJONA/A
(3) C H 3 - C H - C H 2 O H
CH.
OH
CI
(CH
(D) C H 3 - C H 9 - C H - C H ,
3)3CONA
(4) C H 3 - C - C H 3
CH.
Codes:
A
4
4
3
3
(a)
(b)
(c)
(d)
Q.25
C
1
2
2
1
D
2
1
1
2
Listn
List I
(A) Walden Inversion
(B) Racemic mixture
(C) Alkene
Baeyer
(D) Alkene
Codes:
>
(a)
(b)
(c)
(d)
Q.26
B
3
3
4
4
A
3
3
4
4
B
4
4
3.
3
C
2
1
1
2
D
1
2
2
1
List n
List I
(A) CH 3 -C=C- CH 3 c i s - 2 - b u t a n e
(1)Na/NH 3 (/)
(B) C H 3 - C = C - C H 3
(2)H 2 /Pd/BaS0 4
>trans-2-butane
(C) CH 3 C=C-CH 3
> 1-Butyne
(D) C H 3 - C H 3 - C = C H 2 - B u t y n e
A
B
Codes:
2
1
(a)
1
2
(b)
1
2
(c)
2
1
(d)
l&Bansal Classes
D
4
3
4
3
HYDROCARBON
[20]
Q.27
List n
List I
electrolysls
(A) RCOONa
(C)RCOOH
> R-R
Soda lime
(B) R-CH2-COOH
>R-CH 3
(i)AgNO,
(ii)CI2/A
R-Cl
> R-R'
A
B
2
3
1
3
4
2
2
4
D
1
2
2
3
Listn
ListI
Q.28
0
CH2-CH3
C CH,
(A)
o
II
C CH,
CH2-CH3
(2) Stephen's reduction
(B)
HO
(C)
(D)
Q. 29
(A) n-Hexane
(B) CH=CH
List I
Benzene
Benzene
(OCH^CH^CHj
(D) CH3-CH2-X
faBansal
Classes
List n
(1) Wurtz reaction
HYDROCARBON
[21]
Q.30
List I
Baeyer
(A) Alkene
List n
>?
(B)Alkene-^>?
(Q
=~
(D) Alkene
H 2 Pd. .
>9
BaSO.
PhC 3H
>?
followed
by H30
(E) C H , - C = C H 2
|
(i)Hg(OAc)2/HOH
(ii)NaBH4
CH,
(6) Racemic mixture in case of But-2-ene (cis)
(7) Meso compound in case of But-2-ene (cis)
HYDROCARBON
[22]
EXER CISE-II
Q.l
T
> V
.H
(b)COOH.
>
<
H
COOH
R ^ V ^ I
(a) f
W
THF
1.BD3.THF
3
2.D 2 0 2 ,D0
>
CH 3
Q-2
LlA1H
CH3-C-C1
* >
CH 3
Q. 3
Q.4
Q.5
2 H 5 \c
/
= c
/C2H5
,
\
2. H,OZH+
Na H
k M
ALC
D Y
H
Br
O
II
CH.
Q. 6
RF RN IT
3 3
> A+B.WhatareAandB?
O
II
.CH
^c=c ^
NO 2 -CH 2
CH
Q.7
j'
Q.8
Q. 9
0s04
F
'H2
(i) 0 3
(ii) Me2S
HYDROCARBON
(i) H 2 S0 4
(ii) A
C(Ct0H15Br)
[23]
Q.10
bromobutane
>D
'
CH3(CH;)3-CH(K
2, H,0+
KOII, ILO
RSO/.A
A
Na
fused KOH
followed bv NaNH,
Q.ll
= O + CH,CO,H
KMn04(hot)
C h, r L i n d l a x '' s C,,H
g Catalyst
optically
active
Li/EtNH
*.
4 ethyl 2, 4 dimethyl
2, 5 heptadiene
0,/H,o
CSH.04
+ e > C = 0 + CH3CO,H
optically inactive
C.
Q.12
(i)
(ii)
PhCHjCHjCHg + Br2
^ a
>D
u/nh,
- E
hot KMnQ4
^ Q
vOH
CH,
(Mi)
Me
(v)
Me
H3C OH OH
(iv)
OH
CF3 - CH = CH2
Me Me
(!lBansal
Classes
HYDROCARBON
[24]
(i)
('")
->
COjMe
Ph
o
l.NaNH2(3equiv.)NH3 ^ g
2. CH3I
Q 14 (i) Compare the reaction of CH2 = CH, & CF2 = CF2 with NaOEt in EtOH
(ii) CC1, = CC12 does not decolourise Br2 solution - explain.
Q.15
(i)
(ii)
Q.18
Conversion:
(i) C2H2
racemic 2, 3 dibromobutane
(ii) 2 butyne
(iii) Ethyne
Acetone
(iv) Methane
> n Butane
Conversion:
(i) C2H2
> ethylidene diacetate
(iii) C,H,
> m nitroaniline
> 2 pentyne
(v) Ethene
Q.19
Q.20
Q.21
fa Bansal
Classes
Propionic Acid
HYDROCARBON
[25]
Q.22
When citral is allowed to react in presence of dilute acid with olivetol, there is obtained a mixture of
products, one of which is drug marijuana. Reaction is as follows.
Me2C = CH - CH2-CH2-CMe=CH-CHO +
[ q !
O H ^ ^ Q H ,
(0/~C'H"
\
\ _
(marijuana)
Explain the mechanism.
Q.24
The following cyclisation has been observed in the oxymercuration & demercuration of this unsaturated
alcohol. Propose a mechanism for this reaction.
2. NaBH 4
Q.26
(a)
MeCH2-C=CBr + CH=CMe
Cu+
> A
CI
(b)
0H
CH 2 -CHC1 2
>B
OH
(c)
CH2 = C H - C H - C H = C H - C H , l e O H > C
(d)
\C=CH
(e)
C13C-CH=CH2
(0
/ - Y *
H2S04
H2SO4/H2O
OH
HQBr
rS
> F
>
3Z"20
>
HYDROCARBON
[26]
Q.27
Acetylene is acidic but it does not react with NaOH or KOH. Why?
Q.28
CH=C-CH 2 -CH=CH 2 , adds up HBr to give CH^C-CH 2 -CHBr-CH 3 while CH=C-CH=CH2 adds
up HBr to give CH2=C . Br . CH=CH2.
Q.29
Chlorination of ethane to ethyl chloride is more practicable than the chlorination of n-pentane to
1-chloropentane.
Q.30
Q. 1
EXERCISE-HI
0.37 gm of ROH was added to CH3MgI and the gas evolved measured 112 cc at STP. What is the
molecular wt. ofROH ? On dehydration ROH gives an alkene which on ozonolysis gives acetone as
one of the products ROH on oxidation easily gives an acid containing the same number of carbon
atoms. Gives the structures ofROH and the acid with proper reasoning.
Q.2
Q.3
There are six different alkene A, B, C, D, E and F. Each on addition of one mole ofhydrogen gives G
which has the lowest molecular wt hydrocarbon containing only one asymmetric carbon atom. None of
the above alkene give acetone as a product on ozonolysis. Give the structures of A to F. Identify the
alkenes that is likely to give a ketone containing more than five carbon atoms on treatment with a warm
conc, solution of alkaline KMn0 4 .
Q.4
3,3-dimethyl-1 -butene and HI react to give two products, C 6 H, 3 I. On reaction with ale, KOH one
isomer, (1) gives back 3,3-dimethyl-l-butene the other (J) gives an alkene that is reductively ozonized
to Me 2 C=0. Give the structures of (I) and (J) and explain the formation of the later.
Q. 5
Three isomeric alkenes A, B and C, C5HR) are hydrogenated to yield 2-methvlbutane A and B gave the
same 3 ROH on oxymercuration - demercuration. B and C give different 1 ROH's on hydroboration
-oxidation. Supply the structures of A, B & C.
Q.6
Two isomeric alkyl bromides A and B (C5H, ,Br) yield the following results in the laboratory. A on
treatment with alcoholic KOH gives C and D (C 5 H, 0 ). C on ozonolysis gives formaldehyde and
2 methyl propanal. B on treatment with alcoholic KOH gives only C (C 5 H ]0 ). Deduce the structures of
A, B, C andD. Ignore the possibility of geometrical and optical isomerism.
Q.7
(a)
(b)
(c)
Q.8
An alkylhalide, X, of formula C 6 H )3 Clon treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H,2). Both alkenes on hydrogenation gives 2,3-dimethylbutane predict the stmctures
ofX, YandZ.
Q.9
Identify a chiral compound C, C, 0 H. 4 , that is oxidized with hot KMn0 4 to Ph COOH, and an achiral
compound D, C lt ,H ]4 , inert to oxidation under the same conditions.
HYDROCARBON
[27]
Q.10
C7H14 (A) decolorises Br2 in CC14 and reacts with Hg(OAC)2 in THF. H 2 0 followed by
compound (C) obtained by oxidation of 3-hexanol with KMn0 4 . Identity A, B and C compound D,
and isomers of A reacts with BHV THF and then F I ^ / O H to give chiral E. Oxidation of E with
KMn0 4 or acid dichromate affords a chiral carboxylic acid F. Reductive Ozonolysis of D, gives the
4
F and G.
'
Q.ll
Q.13
A hydrocarbon A, ofthe formula CgH10, on ozonolysis gives compound B (C4H602) only. The compound
B can also be obtained from the alkylbromide (C3H5Br) upon treatment with magnesium in dry ether,
Q.14
An organic compound (A), C6H10 on reduction first gives (B), C6H12 and finally (C), C H [4 . (A)
h
Q.15
OF)'
"d fi d K M n O ^ ^ ^
'
V 6 S m
C2l 4
J ^
f E ) C
f f
0xidati
no^B)
Compound A (C6H]2) is treated withBr2 to form compound B (C6H12Br2). On treating B with alcoi
KOH followed by NaNH, the compound C (C6H10) is formed. C on treatment with H2/Pt fo
2-methylpentane. The compound ' C does not react with ammonical Cu2Cl2 or AgN0 3 . When
treated with cold KMn0 4 solution, a diol D is formed which gives two acids EandF when heatec
KMn04 solution. Compound E is found to be ethanoic acid. Deduce the structures fromAto F.
(A) give snoj>pt. with Ag(NH 3 V andgfves optimally inactive (CX C 8 H, 4 ^ t h Hjnpreser
Q.17 A
HYDROCARBON
Oxidation ofB wi
[28]
Q.20
6g sample of a natural gas consisting of methane (CH4) and ethylene (C2H4) was burned with excess of
oxygen and 17.2g of carbon dioxide and some water was obtained as products. What percent by
weight of the sample was ethylene.
Q. 1
Q.2
EXERCISE-IV
Q. 3
(A)
[IIT4 90]
[IIT'90]
(D) ethene
[IIT 491]
(D) 2-butanol
Q4
The hybridisation of carbon atoms in C-C single bond ofHCsC-CH=CH 2 is (A) sp3-sp3
(B)sp 2 -sp 3
(C) sp-sp2
(D) sp2-sp2
Q.5
The product(s) obtained via oxymercuation (HgS04 + H 2 S0 4 ) of 1-butyne would be (A) CH3 - CH2 - C - CH ,
[IIT '91]
II
o
Q. 6
Q.7
Q.8
Q. 9
Which one ofthe following alkenes will react fastest with H2 under catalytic hydrogenation condition [IIT '2000]
R
(A) ; > = (
H
yH
R
\
H
H
R
\
R
\
CD) /
R
[IIT4 99]
[IIT42000]
(D)AgN0 3 in ammonia
In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markovnikov
addition to alkene because [T1TS42001]
(A) both are highly ionic
(B) one is oxidising and the other is reducing
(C) one of the step is endothermic in both the cases
(D) All the steps are exothermic in both cases
HYDROCARBON
[29]
The reaction of
(A) H+
(C) OH
ia the addition of
(B) CR in first ste
(D)C1 and OH
I HOC! I
[IIT'2001]
[IIT'2001J
Q.14
Q.15
: MOW
H 3 C - C H - C H - C H 3 +Br - ' X ' + :
(A) H3C - CH - CH - C H 2
I>
(C) H 3 C - C - C H - C H 3
1,
(B) H 3 C - C H - C - C H 3
J, u
CH 3
(D) H 3 C ~ C H - C H - C H 3
Q.16
(A) bromine, CC14
(C) dilute H 2 S0 4 ,HgS0 4
Q 17
(B)H2J
C 6 H 5 -C=C-CH 3
( A ) N A @
(B)Y-<o)
HYDROCARBON
on
[30/
Q.18
OH
H+
" _H
(mixture)
|1IT'20031
(C) 4
(D) 5
[IIT' 2004]
(D) NaBH 4
Q.20
When Phenyl Magnesium Bromide reacts with tert. butanol, which of the following is formed?
(A) Tert. butyl methyl ether
(B) Benzene
(C) Tert. butyl benzene
(D) Phenol
[IIT '2005]
Q.21
1 -bromo-3 -chlorocyclobutane when treated with two equivalents ofNa, in the presence of ether which
ofthe following will be formed?
[IIT'2005]
/Br
/CI
(A)
Q. 22
(B)
( C ) [ J
(D)
Q.23
CH 3 -CHCH 2 + NOC1 - P
Identify the adduct.
[IIT 2006]
CH3-CH-CH,
(A)
I
CI
CH3-CH-CH2
!
NO
(B)
W
NO
J
,
C Hi33,
- C H 2, ~~- CH
(C)
,
(D)
CI
I
I
NO CI
NO
CI
CH,
Q.24
H.C^I
CH
Ci
2'hv
i&Bansal Classes
(B) 6, 4
fractional
(C) 4, 4
HYDROCARBON
distillation
M(isomeric products)
(D) 3, 3
[IIT 2006]
[31]
EXERCISE-IV
(B)
CI
Q.l
^
Q.2
C6H5CH2CHCH3
ale. KOH
>?
[IIT 1992!
HBr ^
[ I I T 19931
Br
Q. 3
Q. 4
C ( C 6 H j 2 ),
R-CEEC-R
Q. 5
[IIT 1994]
Ho
Lindlar catalyst
Write down the structures of the stereoisomers formed when cis-2-butene is reacted with bromine.
[ I I T 1995]
Q.6
An organic compound E(C 5 Hg) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis
gives formaldehyde and 2-ketopropanal. Deduce the structure of compound E.
[IIT 1995]
Q. 7
Give the structures of the major organic products from 3-ethyl-2-pentene under each of the following
reaction conditions.
[IIT 1996]
HBr in the presence of peroxide
(b) B^/F^O
Hg(0Ac) 2 /H 2 0;NaBH 4
(a)
(c)
Q.8
An alkyl halide, (X) offormula C6H13C1 on treatment with potassium tertiary butoxide gives two isomeric
alkenes (Y) and (Z) (C 6 H ]2 ). Both alkenes on hydrogenation give 2,3-dimethylbutane. Predict the
structures of (X), (Y) and (Z)
[ITT 1996]
Q.9
Q. 10
One mole of the compound A (molecular formula C8H12), incapable of showing stereoisomerism, reacts
with only one mole of H 2 on hydrogenation over Pd. A undergoes ozonolysis to give a symmetrical
diketone B (C 8 H 12 0 2 ). What are the structure ofA and B?
[IIT 1997]
Q. 11
Compound (A) C 6 H 12 gives a positive test with bromine in carbon tetrachloride. Reaction of (A) with
alkaline KMn0 4 yields only (B) which is the potassium salt of an acid. Write structure formulae and
IUPAC name of (A) and (B).
[UT 1997]
Q.12
The central carbon-carbon bond in 1,3-butadiene is shorter than that of n-butane. Why?
Q.13
[ I I T 1998]
C6H5CH(OH)CEECH
Q 14
->c6h5ch=chcho
fa Ban sal
Classes
[IIT 1998]
HYDROCARBON
[IIT 1998]
[32]
Q.15
Q.16
Discuss the hybridisation of carbon atoms in allene (C3H4) and show the 7i-orbital overlaps
[IIT 1999]
Complete the following [IIT 1999]
Q.17
[IIT 1999]
D
/
HO
/=c\
H,CC
H
3
/ \
H3C
CH,.
Q.18
c h
A . > H 33CC
/ N
CH 3 CH 3
Explain briefly the formation on the products giving the structures of the intermediates.
(i) H,C
C H
HCl
> H,C
OH
r,
+ I
2 \
/CH~CH
[IIT 1999]
- C l + etc.
But
CH 3
! 3
CH
(ii)
CH,
H
HCl
OH
H,C
H,C
C
Ho
CI
| HI' 1999]
Carry out the following transformation in not more than three steps.
O
[IIT 2000]
Q.21
[IIT 2000]
CH,
CH3-C-CH,Br
'
'
CH,
C2H5OH
(ii)
CH,
H,
Lindlar'sCatalyst
Q.22
On reaction with 4N alcoholic KOH at 175 C 1-pentyne is slowly converted into equilibrium mixture
of 1.3% 1-pentyne (A), 95.2% 2-pentyne (B) and 3.5% 1,2-pentadiene (C). Give the suitable
mechanism of formation ofA, B and C with all intermediates.
[IIT 2001]
Q.23
Identify X, Y and Z in the following synthetic scheme and write their structures. Is the compound Z
optically active? Justify your answer.
[IIT 2002]
CH3CH,C-=-C-H
fa Ban sal
Classes
(i) NaNH2 ^ ^
H2/Pd-BaSQ4 ^ y
alkaline KMnQ4 ^ j
(ii)CH3CH2Br
HYDROCARBON
[33]
Q.24
(a)
(b)
Q.25
A biologically active compound, Bombykol (C ]6 H 30 O) is obtained from a natural source. The structure
of the compound is determined by the following reactions.
On hydrogenation, Bombykol gives a compound A, C 1 6 H 3 4 0, which reacts with acetic anhydride to
give an ester.
Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis
( 0 3 / H 2 0 2 ) gives a mixture of butanoic acid, oxalic acid and 10-acetoxy decanoic acid.
Determine the number of double bonds in Bombykol. Write the structures of compound Aand Bombykol.
How many geometrical isomers are possible for Bombykol?
j LIT 2002J
If after complete ozonolysis of one mole of monomer of natural polymer gives two moles of CH2Q
andone mole of O = C - CH = 0 . Identify the monomer and draw the all-cis structure ofnatural polymer.
[IIT 2005]
[IIT 2005]
Identify X and Y.
^Bansal Classes
HYDROCARBON
[34]
ANSWER KEY
EXERCISE-I
Q.l
Q.8
Q.15
Q.22
Q.29
Q.36
Q.43
Q.50
Q.57
Q.64
B
C
B
C
B
B
B
A
C
C
Q.2
Q.9
Q.16
Q.23
Q.30
Q.37
Q.44
Q.51
Q.58
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.52
Q.59
A
C
B
D
B
A
B
A
C
A
C
D
A
C
A
B
C
C
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
Q.53
Q.60
(A)
Q.5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
Q.54
Q.61
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
Q.55
Q.62
A
B
B
A
A
B
B
A
A
Q.3
Q.7
Q.ll
Q.15
Q.19
A,B,C,D
A,B,C
A,B
A,C
A,D
Q.4
Q.8
Q.12
Q.16
Q.20
A,B,C,D
A,B,C,D
A,C
A,B,D
D
Q.24
Q.28
Q.30
Q.25 (c)
(c)
(A) 4; (B) 3; (C) 1; (D) 3,4
(A) 4,7;(B)5,6; (C)3,4; (D)5,6 ; (E)2
EXERCISE-I
Q.l
Q.5
Q.9
Q.13
Q.17
Q.21
Q.23
Q.26
Q.29
Q.2
A,C
A,C
Q.6
A,B
B,C
Q.10 A,B
A,C
Q.14 B,D
B,C
Q.18 B,C,D
A,C,D
Q.22 A,C,D
B,D
(A) 3,4 ; (B) 3,4 ; (C) 1,2;(D)2
Q.27 (a)
(d)
(A)5,7 ; (B) 4,5 ;(C) 3 ; (D) 1,2,6
Q.7
Q.14
Q.21
Q.28
Q.35
Q.42
Q.49
Q.56
Q.63
A
A
D
B
D
B
C
C
D
D
D
B
A
A
D
A
C
A
C
A
B
C
B
A
A
C
A
(B)
EXERCISE-II
coo w
coo
Q.l
(a)
(b)
H
BH,
-D
DO-
HO
-H
Q.3
CHL-C = CH?
C,HC
OH-
OH-
"H
O = CH
-H
H-
c2H5
H D
-OD
C,H<
-OH
Q.4
H-
O = CH
CH2-CH2-C-H
n_CH=i
CH=0
-H
COO
COO
CFL
Q.2
D-
-OH
C?H=
CH 7 NO 2
-CHO
Q.5
Q.6
-CHO
CH^NOt
l&Bansal
Classes
HYDROCARBON
[35]
Q.7
CH 2 = C H - C H 2 - C H 2 - C H 2 - N - C H 3
CH 3
c
Q.8
Q.9
a-pinene ->
(A) =
V ^ ^ B r , (B) =
Me
OH
Q.10
Br
(C) =
Me
^ / V ^ r
0 H
ONa
C-C-C-C-C-C-C-C-C,(F)C-C-C-C=C-C-C-C-C,
OH
Br
(G) C - C - C - C - C - C - C - C - CV(H) C - C - C - C s C - C - C - C - C
Br
C-C
Q.ll
C-C
C-C
(A) C - C = C - C - C = C - C , (B)cis C - C = C - C - C = C - C , ( C ) H O O C - C - C O O H ,
C
C-C
(D) H - C - C O O H
i
c
Q.12
Phv
c
H /
= c
/H
Ph-CH-Et
\ c H _ A r ,(D)
^
OH
OH
HYDROCARBON
[36]
Q.13
(i)
> (iv)noreaction
/ ^ L
Br
W(A)p
Q. 14
_l
C H 2
B r
,(B)Ph-C,C^H
Q.25
O-CH3
Q.26
Ii
(D) <^JyC-CH3
Br
I
C 1
CI
I - CH,
, ( Q CH 2 = CH - CH == CH - CH
OH
I
0
(G) A
/ \ / \ A0
EXERCISE-UI
H 13 C \
>
H3C/
Q.l
Q . 2 (A)
CH-CH,OH
CH,
(B)
I '
(D)
Q.3 (A)
CH^CHCH^ CH^
CH3
I
HjC-CH-C^CHjCl
(G)
CHXHXH,
(B)
(G)
CHg-CH-CH^ CFL
CHXHXH,
<F)
CH3
I
H3C-CH-CH-CH3
I
CI
CH3
I
H 3 C-C=CH-CH 3
CH 2 =C-CH ; CH 3
CH 2 -CH=CH 2
CH3
I
C1CH,- CH-CHXH,
I
CH--C-CHXH,
I
CI
(D)
(C)
CH3
CH3COCH3
CHCHXH,
(H)
(C)
I
CH3-CH-CHXH3
CHf-CCH^CH^
(E)
C^CHjCHj
I
CH3COOH
CH=CH-CH3
(F)
CH,-C=CH-CH 3
CHXH^CH^
I
CH 3 -CH-CH=CH 2
H 3 C-C-CH 2 CH,
i
H
fa Ban sal
Classes
HYDROCARBON
[37]
Q.4
(I)
CH3
(J)
CH3 CH3
I
I
Q.5
CH3-C- CH-CH3
CH3CH-C-CH3
I
CH3
I
I
(A) CH3-C=CH-CH3
(B)
(C)CH2=CHCH(CH3)2
CH2=CCH2CH3
I
CH,
I
CH,
Q.6
CH3
(A)
CH3-CH-CH
(B)
CH
(D)
CH^r-CH^-CH-CI^
(Q
CH2=CH-CH-CH3
CH3
CH,
CH3CH=C~CH3
I
CH3
Q.7
CH=CH2
(A)
CH3-CH=CH-CH3
Q.8
(X)
:c=c
(B)
CH3-CC1"CH-CH3 (Y)
I
CH^-C* -H
(Q
CH2=C CH-CH3
I
CK^CH^ ]
(Z)
CH3-C = C-CH3
CH3 CH3
Q.9
(A)PhCH(CH3)CH2CH3
CH3 CH3
(B)PhC(CH3)3
Q.10
OH
(D)
CH3
CH3-CH-C-CH2CH3
II
CH2
(E)
CH3
CH3
I
CH3CH-CH-CH2CH3
(F)
CH2OH
O
CHj
I
CHj-CH-CH-CHJ-C^
CO,H
(A) C^CH^CH^-CHCH,
CH3
I
(A) CH 3 -C-C^CH
I
CHj
CH,
(C) H 3 C-C-C=C^CH 2 CH 2 CH 3
CH,
faBansal Classes
(B) CH3CH,CsC-CH,
(C) Cvclopentene
CH3
I
(B) I^C-C-OC" Na+
I :
CH3
CHj
P ) H,C-C-C=CH-CH2CH2CH3
CH,
[38]
NOMENCLATURE OFORGANIC COMPOUND
Q.13
(A)[>-OC^j
(B)[>-COOH
Q.14
(C)[>-Br
CHO
Q.15
(C)
(B) CH 3 -CH-CH-CH-CH3
(A) CH 3 -CH=CH-CH-CH 3
CH 3 -C=C-CH-CH 3
I I I
Br Br CH,
CH3
CH3
(F)
(E) CH3COOH
(D) CH,-CH-CH - C H - C H ,
i
I I
OH OH CH,
H 3 C-CH-COOH
I
C^
H
l
Q.16
CH3-C = C - C - C = C-CH3
I I I
H
Q.17
Q.18
CH3
CH,CHXH= CHCH,CH3
(A) C H 3 - C H = C H - C H = C H - C H 3 ,
(B) C H 3 - C H 2 - C H = C H - C H 2 - C H 3 ,
(C) C H 3 - C H 2 - C H 2 - C H 2 ~ C H 2 - C H 3 ,
Q.19
CHO
(D)CH3CHO, (E) I
, (F) C H 3 C H 2 C O O H
CHO
Isomer are : C ^ C - C - C , C = C - C = C , C = C = C - C ,
Q.20 23.7
EXERCISE-IV
Q.l
Q.6
Q.ll
Q.16
Q.21
C
D
C
D
Q.2
Q.7
A,D
A,C
Q.12
Q.17
B
A
Q.22
Q.10
Q.15
D
B
Q.20
B
B
Q.19
Q.24
Q.23
Q.2
Q.5
Q.18
Q.8
CH 2 -CH-CH 3
CH, - C = C H - C H ,
C
A
A
Q.13
EXERCISE-IV
Q.l
(A)
Q.4
Q.9
Q.14
Q.3
(B)
ALC. KOH
CH=CH-CH,
Br
(L,H-CH9-CH3
* F O
CH3
H
Q.3
C H 3 - C H 2 - C - C H = CH2
Q.4
/R
,C = C
-H
I
CH3
(C6H12)
l&Bansal Classes
HYDROCARBON
[39]
Me
Q.5
Br-
CH 2 CH2
Me
"Br
Br-
-H
H-
-Br
"H
Me
Q.6
(E) CH, - C - CH
Me
OH
Br
Q.7
Q.8
CH 3 CH 3
CH 3 CH 3
CH 3 CH 3
C H 3 - C - C H - C H 3 ; ( Y ) C H 2 = C - C - C H 3 ; (Z) C H 3 - C = C - C H 3
CI
Q.10
(A)
Q.ll
(A)CH3-CH2-CH=CH-CH2-CH3
Q. 16
Q.17
Q. 19
Q.20
< B >o 0
(B) CH 3 CH 2 COOK
CH,
Q.21
(i) CH 3 - C - C H 2 - CH 3
(ii) I
-CH,
Et
Et
CH,
O-C2H6
Et
(Y)->H>C=C<H
(X) Et-CsC-Et
Q.24
Bombykol :- H O - C - C - C - C - C - C - C - C - C - C = C - C = C - C - C - C
(A): - HO-tCH^ 5CH3 4 geometrical isomers are possible
Q.25
)^
-OH
Q.23
CH 3
-OH
Et
(a) CH 2 = C - CH = CH 2
(b)
(CH2
Q.26
( X ) I ^ J ,(Y) C H 3 - C - ( C H 2 ) 4 ~ C H = 0
CH,
l&Bansal Classes
HYDROCARBON
[40]
<1
BANSAL CLASSES
CHEMISTRY
TARGET
IIT JEE
2007
XI(PQRS)
llllllllllilllllilllll li|i|||||!ill||ll|||il||i;;:,
..,:|||lllllllllllllllll
NOMENCLATURE
OF
ORGANIC COMPOUNDS
CONTENTS
EXERCISE-I
EXERCISE - II
ANSWER KEY
IUPAC
Nomenclature according to IUPAC system involves use offollowing terms:
(i)
(ii)
(iii)
Word root:
Prefix: The part of the name C appears before the word root is called prefix. Different prefixes are
used for dif categories of group as:
(a)
Alkyl groups:
CH3-CH2-CH2
> 1-propyl
CH3-CH-CH3
> 2-propyl
CHj-CH^CHj-CT^
> 1-Butyl
CH3-CH2-CH-CH3
> 2-Butyl
CH,
CH, - CH - CH,
(b)
2-Methyl-l-propyl
In IUPAC system,for nomenclature some groups are not considered as functional group but
treated as substituent. These functional group are always indicated by prefixes instead of
secondary suffixes.
-N02
Mtro
-OR
Alkoxy
-CI
Chloro
-Br
Bromo
-I
Iodo
-F
Fluoro
-N=0
Nitroso
-N02
Nitro
=N
Diazo
tBansal Classes
"[250]
(c)
In polyfunction^ compound, one ofthe functional group is treated as principal functional group
& indicated by secondary suffix while other functional groups are treated as substituents &
indicated by prefixes.
GF
R-OH
R-SH
R-NH 2
R-CHO
RCOR
RCOOH
Amides
Acid chloride
Ester
Nitriles
Suffix
ol
thiol
amine
al
one
-oic acid
amide
ayl Kc^de.
oate
nitriie
O.Co.
Alcohols
Thioalcohols
Amines
Aldehyde
Ketone
carboxylic acid
RCONH 2
RCOC1
RCOOR
R-C=N
IUPAC Name
alkanel
alkanethiol
alkanamii^o
alkanal
alkanone
alkanoic acid
alkanamide
alkanoyi chloride
alkylalkanoate
alkanenitrile
,
Arrangement:
-rn,
Prefix
Hydroxy
Mercapto
Amino
formyl
Keto or oxo
Carboxy
Carbamoyl
Chloroformyl
Carbalkoxy
Cyano
Methyl but an ol
CH 3
(i)
Rules:
For saturated compounds:
Selection of longest chain :
(a)
Longest continuous chain of carbon atoms is selected. This is called parent chain while all other
C atoms C are not included in parent chain is called side chain.
<
->6
C-C-C-C-C
c
(b)
If more than one set oflongest chains are possible, the chain C max. no. of substituant acts as
parent chain.
c-c-c-c-c-c
c-c
c
(ii)
%k
<5
C-C-C-C-C
(b)
CH,
If two different alkyl groups or substituents are at same position from opposite ends, lowest no.
is given in alphabetical order.
* 2 & 4 &
^
c-C-C-C-C-C-C
-4
jS
<-t
CH 3
faBansal Classes
C,H-
NOMENCLATURE
OF ORGANIC COMPOUND
JJ
(c)
If two different substituents are at same position from opp. ends, lowest no. is assigned in order
of their alphabets.
1
c-c-c-c
I I
I I
CI I
itvs H j o v v J ^
C4OYV6L VW r. a c
c-c-c-c
CI Br
If more than two substituents & side'chains are present, the sum oftheir numbers should be
lowest at the first preference irrespective of the nature of substituent or side chain. This is K/a
"VDOUU
S u t e S * ^
Jvaue, ^
Series ^
locamts
Z0
CcwkiiHirfy
C-C-C-C-C C-C
"c%at
CH, CH,
C H
C-C-C-C-C
CI I
CH,
3
Br
.
Jre^rm-s exc^e- *
In^asewheh starting loeant is lo^erfrom cfie sid, then lowest sum rule is n6t obeyed.
Cotv^oW,
-teawtyW,,
t-b-C-d-C-C-C-t-t-C
Sashes
(iii)
o c t e t s ;on. c^
sk.c&<ii4
VVO. C7T\
C C
1st
Arrangement of prefixes :
(a)
Side chain or substituent group are added as prefix C its loeant in alphabetical order.
CH3-CH-CH-CH,
CI
2-bromo, 3-chlorobutane
Br
H , C - C H - C H - C H 2 - CH 3
3 chloro, 2-methyl butane
CH3 CI
(b)
If more than one similar alkyl group or substituents are present terms, tri like are used.
CH 3
I
H,C C CH-,
|
CH 3
(c)
2,2-dimethyl propane
2;3-dimethyl
In case side chain is also branched, it is also numbered form carbon atom attached to main chain
& is generally written in brackets.
3
4
5
6
7
CH, - CH 2 CH CH 2 CH 2 CH 2 CH 3
2 CH-CH3
1 CH 3
tBansal
Classes
NOMENCLATURE
OF ORGANIC
COMPOUND
3-ethyl-2-methyl heptane
1
2
3
4
5
6
7
8
CH 3 - CH - CH2 - CH2 - CH - CH2 - CH2 - CH3
I
CH3
1 CH-CH3
2 CH3
c-c-d-c-c-c-c-c-c-c
-CP(CH3)#
(i)
- -
c-c-c-c-c-c
Ifl i
- .
(ii)
- -
(Si)
If double & triple bonds are at same position from either ends, lowest no is assigned to double bond
1 2
c=c-c-c=c
(iv)
If both alkene & alkyne group are present, the org. compound is named as derivative of alkyne rather
than alkene.
CH 3 -H=CH-C=CH
Pent-3-en-l-yne
In some cases all the double & triple bonds present in molecule can't be included in longest chain. In such
cases following prefixes.
CHJ =
CH3-CH=
Methylene
Ethylidene
CH=CEthynyl
faBansal Classes
CH 2 =CHEthenyl
[5]
(i)
OH
c
(ii)
The carbon atom of functional group is to be included in deciding the longest carbon chain.
C-C-CN
3 carbon chain
C-C-C-CHO
4 carbon chain
(lii)
The lowest no is assigned to functional group even if prior rules are violated.
O
|
CH3
CH,
4|
CH 3 -C-CH 2 -CH-CH 3
I
(iv)
CI
1
The order ofnumbering a carbon chain, thus follows the order:
(a)
Functional group
(b)
Unsaturation
(c)
Substituents & side chains
7
5 4
3 2
c=c-c-c-c-c-c
I
OH
1
3 4
5 6
c=c-c-c-c-c-c
I
OH
(v)
If more than 1 functional group; then choice ofprincipal functional group is made on the basis following
order of preference:
0
I!
II
II
II
II
faBansal Classes
NOMENCLATURE
OF ORGANIC
COMPOUND
[6]
EXERCISE - I
Q. 1
How many 10carbon atom will be present in a simplest hydrocarbon having two 3 and one 2 carbon
atom?
(A) 3
(B)4
(C)5
(D)6
Q.2
C 3 H 6 Br 2 can shows:
(A) Two gem dibromide
(C) Two tert. dibromo alkane
Q.3
^QA)
(D) 6-octyn-2,4-diene
t,
5
, ,
H~C =
(B) 3-formyl butanedial
(D) 1,1,3-ethane tricarbaldehyde
CN
(B) 2-formyl-3 -oxopentanenitrile
(D) 1,3-dioxo-2-cyanopentane
(A) 2-cyano-3-oxopentanal
(C) 2-cyano-l,3-pentanedioiifc
Q.6
Q.7
(Wet
^ o V ^ ^ ^ ^ ^
II
II
C=OO
CH 3
(B) 2,2 acetyl-1-methoxy ethanone
(D) None
faBansal
Classes
NOMENCLATURE
OF ORGANIC
COMPOUND
Q.9
Q.10
HO - C = O CH 3
I
I
The IUPAC name of compound CH3 - C = C C - H is:
I I
NH 2 CI
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid
(B) 3-amino-4-chloro-2-methyl-2-pentenoic acid
(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid
(D) All ofthe above
Q.LL
Q.12
Q .13
Q.14
Q.15
(C) Diketone
How many carbons are in simplest alkyne having two side chains?
(A) 5
(B)6
(C)7
(D) Diols
(D)8
CH3 - CH - COOH
I
OH
HO-CH-COOH
I
HO-CH-COOH
CH3C(CH3)2CHO
(C) Pyvaldehyde
CH,
I 3
(D) Iso-octane
faBansal Classes
I
I
CH 3 CH3
NOMENCLATURE
OF ORGANIC COMPOUND
[8]
Q.16 Which of the following pairs have absence of carbocyclic ring in both compounds?
(A) Pyridine, Benzene
(B) Benzene, Cyclohexane
(C) Cyclohexane, Furane
(D) Furane, Pyridine
Q.17 The commerical name of trichloroethene is:
(A) Westron
(B)Perclene
(C)Westrosol
(D)Orlone
CH2CH3
tBansal Classes
"[9]
CI
CH3
(C) CHXH2CH=CHCOCH3 ;
Hex-3-en-2-one
4-Methylpentanal
CH3
Q. 27 The IUPAC name ofthe given compound is:
HO ^
CH3
CH,
Q.29 The IUPAC name ofthe compound Br(Cl) CH. CF3 is:
(A) haloethane
(B) 1,1,1 -trifluoro-2-bromo-2-ch)oroethane
(C) 2-bromo-2-chloro-1,1,1 -trifluoroethane (D) 1 -bromo-1 -chloro-2,2,2-trifloro ethane
Q.30 The group ofhetrocylic compounds is:
(A) Phenol, Furane
(B) Furane, Thiophene (C) Thiophene, Phenol (D) Furane, Aniline
Q. 31 The correct IUPAC name of CH , - CH2 - C - COOH is:
JlOJ
q 34
c > @ '
c h 3
Number of secondary carbon atoms present in the above compounds are respectively:
(A) 6,4,5
(B) 4,5,6
(C) 5,4,6
(D) 6,2,1
Q. 3 5 The IUPAC name of acetyl acetone is:
(A) 2,5-Pentane dione (B) 2,4-Pentane dione (C) 2,4-Hexane dione (D) 2,4-butane dione
Q. 3 6 When vinyl & allyl are joined each other, we get
(A) Conjugated alkadiene
(B) comulative alkadiene
(C) Isolated alkadiene
(D)Allenes
Q.37 Glycerine is:
(A) Propane triol-1,2,3
(C) Propyl glycol
0H
and
(b)l^J
True statement for the above compounds is:
(A) (a) is phenol while (b) is alcohol
(B) Both (a) and (b) are primary alcohol
(C) (a) is primary and (b) is secondary alcohol (D) (a) is secondary and (b) is primary alcohol
Q.39 IUPAC name will be CH2 - CH - CH2
I
!
!
CN CN CN
(A) 1,2,3 -Tricyano propane
(C) 1,2,3-cyano propane
Q.40 A substance containing an equal number of primary, secondary and tertiary carbon atoms is:
(A) Mesityl Oxide
(B) Mesitylene
(C) Maleic acid
(D) Malonic acid
Q.41
or*
IUPAC name of
(A) But-2-ene-2,3-diol
(C) 2-methylbut-2-ene-2,3-diol
(B)Pent-2-ene-2,3-diol
(D) Pent-3-ene-3,4-diol
tBansal Classes
"[11]
Q.43
IUPAC name of
is:
Q.45
The molecular formula of the first member of the family of alkenynes and its name is given by the set
(A) C3H2, alkene
(B) C5H6, l-penten-3-yne
(C) C6Hg, l-hexen-5-yne
(D) C4H4, butenyne
0
CH 2 -C-OH
Q.46
Q.47
c < m
The IUPAC name of compound | xCOOH
CH2-COOH
(A) 1,2,3 -tricarboxy-2,1 -propane
(B) 3-Carbox-3-hydroxy-l,5-pentane dioic acid
(C) 3 -hydroxy-3 -Carboxy-1,5-pentane dioic acid (D) None
The IUPAC name of the compound:
(A) Propylene Oxide
(C) 1,2-Epoxy propane
\ qi_ch 3
(B) 1,2-Oxo propane
(D) 1,2-Propoxide
Q. 48
One among the following is the correct IUPAC name of the compound
H
I
N
(A) N-Formyl aminoethane
(B) N-Ethyl formyl amine
(C) N-Ethyl methanamide
(D) Ethylamino methanal
Q. 49
Q.50
<
OH
is
CH3
HC = CH ^
I
>S
HC = CH /
faBansal Classes
(B)
HC = COOH
I
HC = COOH
NOMENCLATURE
(C)
HC = C H ^
HC = CH
I
>CH2(D) I
HC = C H /
HC = CH
OF ORGANIC COMPOUND
C=0
[12]
Q. 52 The number of primary, secondary and tertiary amines possible with the molecular fomula C3HgN is:
(A) 1,2,2
(B) 1,2,1
(C) 2,1,1
(D) 3,0,1
Q. 53 The IUPAC name of C6H5CH=CH-COOHis:
(A) cinnamic acid
(B) 1 -phenyl-2-carboxy ethane
(C) 3 -phenyl prop-2-enoic acid
(D) dihydroxy-3 -phenyl propionic acid
Q.54 The IUPAC name o f i ^ V CH = CH - CHCH2CH is:
U
c k
(B) 3 -methyl-5-cyclohexyl-pent-ene
(D) 1 -cyclohexyl-3,4-dimethyl-but-1 -ene
II
O
NH
Q 56 The IUPAC name of 0,N
- \0)~
_ CHOis:
s
OCH3
(A) 2-methoxy-4-nitro benzaldehyde
(C) 3-methoxy-4-formyl nitro benzene
C - CH3 is:
Cll2
.C=C.
IK
(A) cis-cis-9,12-octadecan dienoic acid
(C) 9,10-octa decadienoic acid
(CH2)7COOH
,C=C.
is:
x
H W
H
(B) cis-trans-9,12-octadecan dienoic acid
(D) 9,14-octa decadienoic acid
Q. 5 9 The suffix of the principal group, the prefixes for the other groups and the name of the parent in the
structure
CH3
CI
JlOJ
Q. 60
CH, -CHO
I 2
The IUPAC name of OHC - CH2 - CH2 - CH - CH2 - CHO is:
Q. 61
I]
^COCL
is:
(B) C6H5-CH=CH-COOH
(C) CH,-CH=CH-COOH
(D) CH - COOH
II
CH-COOH
Q. 66
(B)H-C-0-CH2-CH3
II
I
O
CH3
(C) C H 3 - C - O - C H 2 - C H 2
II
I
O
CH3
(D)H-C-0-CH-CH3
II
I
O
CH3
CH = CH - CHCH2CH3 is:
Q.67
CH3
tBansal
Classes
"[14]
EXERCISE - II
Q.ll
Q.l
Q.12
Q.2
COOH
Q.13
Q.3
02N
Q.14
Q.4
Q.15
Q.16
q.5
Q
Q.17
CH2-CHCH3
\Q/
q.7
Q.19
Q.8
OH
CH2CH2CH2CH3
Q.20
Q.9
CH3^^CH(CH3)2
Q.21
Q.10
faBansal Classes
CH,
Q.22
|^YC2h5
JlOJ
BivjCH,
CH,
Q.34
Q.23
Q.24
CH3 O
C-CH 3
CH,
^k.C-OCH
Q.35
CH3.CH.
Q.25
CH,
Q.36
CH2CH2CH=CH2
Q.26
Q.37
Q.27
Q.38
C-CH2CH3
Q.28
ff
C-OC2H5
Q.29
0<1
Q.39
Q.40
Q.41
Q.30
Br
Q.42
CHO
Q.31
OH
/CI
Q.43
Q 32
A / C H O
c xBr
N
OH
Q.44
9H3
CHCH2CH3
Q.45
Q.33
NH7
faBansal Classes
-OH
COOC2H5
[16]
CH 3
Q.46
(b) H 3 C - N - C H - C H 2 C H 3
CH 3 CjHJ
Q.47
Q.56
.-OH
Q.48
Q.49
\CsCH
r>
Q.50
O \
Q.51
CI
II
I
CH- - C - CH- - CH - CH,
NH 2
OC 2 H 5
Q.54
CH=CH-CH-CH=CH 2
Me
(a)
faBansal Classes
Me
Me
Me = methyl group
NOMENCLATURE OF ORGANIC
COMPOUND
[17]
ANSWER
KEY
EXERCISE -1
A
C
D
C
B
A
C
A
A
D
Q.3
Q.10
Q.17
Q.24
Q.31
Q.38
Q.45
Q.52
Q.59
Q.66
Q.l
Q.8
Q15
Q.22
Q.29
Q.36
Q.43
Q.50
Q.57
Q.64
B
C
D
C
D
C
D
B
A
B
Q.L
CH, - CH - C - CH 2 - OH
!
CH2-CH3
Q2
Q.9
Q.16
Q.23
Q.30
Q.37
Q.44
Q.51
Q.58
Q.65
B
B
C
C
B
D
D
C
B
A
Q.4
Q.ll
Q.18
Q.25
Q.32
Q.39
Q.46
Q.53
Q.60
Q.67
C
C
D
B
B
A
B
C
D
A
Q5
Q.12
Q.19
Q.26
Q.33
Q.40
Q.47
Q.54
Q.61
B
D
C
B
A
B
C
A
D
Q.6
Q.13
Q.20
Q.27
Q.34
Q.41
Q.48
Q55
Q.62
B
A
D
C
A
B
C
D
C
Q.7
Q.14
Q.21
Q.28
Q.35
Q.42
Q.49
Q.56
Q.63
C
B
D
B
B
A
C
A
C
EXERCISE - II
Q.8
2-ethyl-2-butene-1 -ol
Q.2
CH
=CH-C-CH2
II I
O OH
1 -Hydroxy-3 -Butene-2-one
CH3-CH2-CH-CH2-CH2-CH2
CH
CH3-CH-CH3
Q.9
CH 3 - CH 2 - CH - CH - CH,
4-Ethyl octane
Q.3
3-Ethyl-2,4-dimethyl pentane
OH
NO,
3 -nitro-2-propene-1 -ol
Q.4
CH 3
CH = CH - CH,
Q.10
OH O
I
II
CH,2 = CH - CH - C - C = CH
6
CH 7 = C - CH, - CH - CH ,
2-isopropyl-4-methyl-1 -pentene
Q.ll
4-hydroxy-5-hexene- lyne-3-one
CH,-CH2
CH,
I
C=C-CH
l-Hexene-3-yne
iCN
Q.12
Q.7
CH,-C-CH2-C-CH3
II
II
o
o
Q.13
Cyclopropanecarboxylic acid
3 -methyl-1,4,6-Heptatriene
faBansal Classes
NOMENCLATURE
OF ORGANIC
COMPOUND
[18]
Q.15
1,3,5-cyclohexatriene
Q.16
1,3-cyclobutadiene
Q.17
1,2-epoxy propane
Q.18 2,2,6,7-tetramethylocatane
Q.43
Q.19 3-ethyl-4,6-dimethyloctane
Q.44 2-cyclepenten-l-ol
Q. 20 Butyl cyclohexane
Q.47
Q.24 Isopylidenecyclopentane
Q.25
1,3,4-dimethyl-1 -cyclobutene
Q.50
Q.26
Q. 51
1 -propyl-4-isopropyl-1 -cyclohexene
Q.27
1,2-diethenyl cyclohexene
Q.28
1-cyclohexyl-l-propanone
Q. 53 3-ethoxyl-1 (1 -nitrocyclohexyl)-hexe-4-one-1
Cyclohex-2-en-1,4-dione
Q.54
l,3-diphenyl-l,4-pentadiene
Q. 31 3-(l -hydroxyethyl)-5-methylheptanal
Q.56 Butane-1,4-dioic acid
Q.32 6-Bromo-2-oxocyclohexanecarbaldehyde
Q.33 3-amino-2-sec-butyl-5 -cyclohexen-1 -ol
Q.34 2-bromo-2-methyl cyclopentanone
Q.35 Methyl-2-methoxy-6-methyl-3- cyclohexene
carboxylate
Q.36 Bicylo(2.2. l)heptane
Q.37 9-methyl bicyclo(4.2.1) nonane
Q.38 spiro (2.5) octane
tBansal Classes
"[19]