CLS - ENG 22 23 XI - Che - Target 5 - Level 1 - Chapter 10 PDF

Step-1
Chapter 10
Hydrocarbons
Solutions
SECTION - A
1. Answer (1)
I > II > III
2. Answer (1)
Free radical
3. Answer (4)
COOH
KMnO4
OH–, 
COOH
4. Answer (1)
4 3
5 1
2
6
Major product
5. Answer (4)
Cl
Cl
6. Answer (4)
Correct IUPAC name is 3, 3-Dimethylbut-1-yne.
7. Answer (2)
1
Boiling point 
Branching (isomeric alkane)
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2 Hydrocarbons Solutions of Assignment (Step-1)
8. Answer (1)
CH3 CH3
HBr
CH3 – C = CH 2 CH3 – C – CH 3
Br
9. Answer (3)
Acidic behaviour
HC { CH > CH3 – C { CH > CH3 – C { C – CH3
10. Answer (4)
–NH2 activating and o/p-directing
11. Answer (4)
NHCOCH3
Most reactive towards ESR.

12. Answer (1)
C  C – CH 2CH3 C – CH2 – CH2CH3

Hg2+ , H2O+
O
13. Answer (1)
CH3 (i) O 3
C = CH 2 CH3 – C – CH 3 + HCHO
(ii) Zn/H 2O
CH3
O
14. Answer (2)
CCl3
Br
SECTION - B
15. Answer (4)
16. Answer (1)
17. Answer (2)
18. Answer (1)
19. Answer (4)
20. Answer (2)
21. Answer (1)
22. Answer (1)
23. Answer (1)
24. Answer (3)
Solutions of Assignment (Step-1) Hydrocarbons 3
SECTION - C
25. Answer (1)
26. Answer (3)
SECTION - D
27. Those consecutive alkanes which differ by —CH2 group or by molecular mass 14 are known as homologus
series.
28. Sulphur trioxide acts as an electrophile.
COONa
29. (A) = (B) =
30. cis-isomer has a greater boiling point than the trans-isomer due to greater polarity and consequent stronger
interparticle forces.
OH
NaNH2 C2H5Br H2SO4
31. HC CH HC C.Na HC C CH2CH3 H2O, HgSO4
H2C C CH2 CH3
–NH3 –NaBr
O
Rearrangement
H3C C CH2 CH3
Butan-2-one
32. As a generalised rule, the more is the s-character in the hybrid orbitals used by an atom, the closer are the
bonding electrons to the atom, and the shorter and stronger is the sigma bonds. The decreasing order of
C—H bond length is
sp3 > sp2 > sp
The decreasing order of bond enthalpies is,
H
H
C H C C H
H
H
sp sp2 sp3
h
33. (i) CH4 + Cl2   CH3Cl + HCl
CH3Cl + 2Na + ClCH3  CH3 – CH3 + 2NaCl

Ethane
(ii) CH3COOH + NaOH o CH3COO–Na+ + H2O
Electrolysis
2CH3 COO Na 
H O
 CH3 – CH3  2CO2   2NaOH  H2 
2
Ethane
34. Markovnikov rule states that the negative part of the adding molecule adds to that carbon atom which contains
less number of hydrogen atoms.
+ 
H
CH3 CH CH2 + HBr CH3 CH CH3
Contains less number

of hydrogen atoms
+
CH3 CH CH3 + Br– CH3 CH CH3
(Negative part
of the molecule) Br
CH3 CH3
h
35. (i) H3C C CH3 + Cl2 Cl CH2 C CH3
CH3 CH3
Only one product 2,2-Dimethylchloropropane can be obtained by monochlorination of neopentane.
Cl
(ii) H3 C — CH2 — CH2 — CH2 — CH3 
2
h

Three products or three monochloro isomeric n-pentane can be obtained i.e.,

(a) Cl—CH2 —CH2 —CH2 —CH2 —CH3; 1-chloropentane
(b) H 3C CH CH2 CH2 CH3; 2-chloropentane
Cl
(c) H 3C CH 2 CH CH2 CH3; 3-chloropentane
Cl
36. Saytzeff rule states that greater is the number of attached alkyl groups, greater is the alkene stability. It shows
greater number of hyperconjugative structures raising its stability. Example, the stability order of the alkenes
can be given as follows :
CH3 H CH3 H CH3 CH3 CH3 CH3
CH2 CH2 C C C C C C C C
H H CH3 H CH3 H CH3 CH3
Increasing hyperconjugative structures, hence, higher stability

37. Structural isomers are the isomers having same molecular formula but different structures i.e., different
arrangement of atom or groups of atoms within the molecule. The structure differs due to difference in the
attachment positions. This is the reason they are also known as constitutional isomers.
Stereo isomers are the molecules which have same structural formula but have different relative arrangement
of atoms or groups of atoms in space. They have the same atomic connectivity but different orientation of
atoms or groups in space.

Step-2
Chapter 10
Hydrocarbons
Solutions
 Alkanes (Nomenclature, Classification, Preparation, Properties)
1. Answer (3)
Butane can form n-butane and isobutane.
2. Answer (3)
Due to largest surface area.
Compound Boiling point
2,2-dimethyl butane 50°C

2,3-dimethyl butane 58°C
3-methyl pentane 63°C
2-methyl pentane 60°C
3. Answer (2)
The reaction proceeds in a direction to give most stable free radical as reaction intermediate.
4. Answer (3)
3n  1
CnH2n 2  O2  nCO2  nH2O (Eudiometric equation)
2
5. Answer (1)
(CH3)3 CMgCl + D2O o (CH3)3CD + MgODCl
6. Answer (3)
HIO3 and HNO3 being oxidants oxidize HI and prevent the backward reduction of RI.
7. Answer (4)
It is Wolff-Kishner reduction.
 Alkenes (Nomenclature, Classification, Preparation, Properties)

8. Answer (2)
CH3 CH3
C= C
CH3 CH3
It contains only primary hydrogen.

9. Answer (1)
CH3  CH2  CH2  CH  CH2 CH3 – CH  CH – CH2 –CH3

monosubstituted disubstituted
CH3 — C CH — CH3
CH 3
Trisubstituted
with respect to presence of alkyl groups.

10. Answer (2)
The alkene which has least number of hyperconjugable H's is least stable.
11. Answer (2)
C4H8  Br2  C4H8Br2

2.8 gram 8 gram 10.8 gram
∵ 8 g Br2 reacts with 2.8 g alkene
2.8  160 g
? 160 g Br2 reacts with = g alkene = 56 g alkene
8
Hence alkene is C4H8
12. Answer (4)
HBr (CH3)3COK
Peroxide Br
13. Answer (2)
CH2 HOCl
CH2OH
CH2 CH2Cl
14. Answer (1)
Due to formation of most stable carbocation.
15. Answer (4)
MeO CH CH 2 MeO CH CH 3
H Br
Br
MeO CH CH 3
Br
16. Answer (1)
O
CH CH—C—OH
It is an unsaturated acid hence shows addition with bromine.
17. Answer (3)

Br
CH 2 CH CH CH2
Br
Zn
CH2 CH CH CH2 + ZnBr 2
18. Answer (1)
Conjugated diene is more stable than isolated or cumulated dienes.
19. Answer (2)
As HCl does not give peroxide effect the reaction of HCl even under the presence of peroxide proceeds through
ionic mechanism.
Cl
Cl
CH3 – CH = CH2 CH3 – CH – CH3 CH3 – CH – CH3
H – Cl reactive
intermediate
20. Answer (1)
H H
H O OH
H O H –H
H3C C CH2 H3C C CH3 H3C C CH3 H3C C CH3
CH3 CH3 CH3 CH3

21. Answer (1)
Cl2/H2O
CH3 – CH = CH2 CH3 – CH – Cl2
OH Cl
22. Answer (4)
H3C H3C H
(i) O 3
C = CH2 (ii) Zn – H 2O
C = O+ O= C
H3C H
H3C
isobutylene (A)
KMnO4 ,

CH3
Give +ve test with
Baeyer's reagent HCOOH + O = C
CH3
23. Answer (3)
O3 COOH
2CH2
H2O2 COOH
24. Answer (2)
D D
O3
Zn – H2O
O
CHO
 Alkynes (Nomenclature, Classification, Preparation, Properties)

25. Answer (2)
Removal of Br and H from D & E carbon is called dehydrohalogenation
26. Answer (1)
HBr
CH2 = CH – C  CH CH2 = CH – C = CH2
Br
Conjugated diene
27. Answer (2)
R
R C C R C C
e R
(Radical anion) – a reactive intermediate
 Aromatic Hydrocarbons (Preparation, Properties)

28. Answer (1)


E E
most stable
benzyl carbocation
Other unsaturated compounds give less stable reactive intermediate when treated with electrophile.
29. Answer (1)
OCH3 CH3 CF3
> > >

+ M effect Hyperconjugation – I effect
30. Answer (2)

Friedel Crafts alkylation involve conversion of Arene into alkyl arene in the presence of acids (Lewis acid as
mineral acid). But in example (2), alkyl halide is obtained from alcohol.
31. Answer (01)
Only one isomer is possible.
32. Answer (10)
Cl2CH — CH — CH2CH3 CH3 — CH — CCl2 — CH3
CH3 CH3
CH3 — CH — CH2 — CHCl2 Cl — CH2 — CH — CH2CH3
CH3 CH2Cl
Cl — CH2 — C(Cl) — CH2CH3 Cl — CH2 — CH — CH(Cl) — CH3
CH3 CH3
Cl — CH2 — CH — CH2CH2Cl CH3 — C(Cl) — CHCl — CH3
CH3 CH3
CH3 — C(Cl) — CH2CH2Cl CH3 — CH — CH(Cl) — CH2Cl
CH3 CH3
33. Answer (05)
Possible isomers with molar formula C4H6
, , , ,
34. Answer (28)
COOK H H
Electrolysis
+ 2CO2
COOK H H
35. Answer (06)

C4H8  6O2  4CO2  4H2O
Moles of O2 available = 6
Volume = 6 × 22.4 = 134.4 litre
36. Answer (12)
Given molecule has 12 = 'CH2' groups that will give 12 HCHO molecules upon reductive ozonolysis.
37. Answer (05)
Reactions a, b, c, d, e are example of regioselective reactions.
38. Answer (10)
Naphthalene has 10S electrons.
39. Answer (06)
O
is electron withdrawing group and –NH– is electron donating in nature.
H
So, EAS will occur according to –NH– group.
40. Answer (12)
P= Q=
O O
a=6 b=6
Previous Years Questions

41. Answer (1)
OH O
CH3
+ O AlCl3
OH OH
CH3 CH3
O
AlCl3O O
42. Answer (4)
Contain 6Se– in complete conjugation and are aromatic.
is anti-aromatic as it has 4Se– in complete conjugation.
43. Answer (2)
MeO
CH2–Cl
AlCl3
MeO +
MeO
+
MeO
44. Answer (1)

h
CH3 – CH2 – CH  CH2  Br2 
 CH3 – CH– CH  CH2
|
Br
45. Answer (2)
N 
HNO3

| Conc. H SO
2 4
H
Activated Deactivated
ring ring
? Major product will be formed as per activating group.
? Product formed is O2N

O
N
|
H
46. Answer (1)
is aromatic as it has 2Se– in complete conjugation
and are antiaromatic.
is non aromatic
47. Answer (1)

Cl
HO HO
(1) HCl
AlCl3
HO +
HO
+ AlCl4–
(Major product)
Para attack will form major product because at ortho position steric crowding is applicable.
48. Answer (1)
In general, polarity increases the intermolecular force of attraction and as a result increases the melting point.
49. Answer (1)
50. Answer (3)

HBr
CH3O CH == CH — CH3
Excess
HO CH — CH2 — CH3
Br
51. Answer (3)
CH3
CH3
CH2
+
HCl C
CH3
–
Cl
CH3
C Cl
CH3
52. Answer (2)
O
Cl O
(i) AlCl3, Heat
C
+ O (ii) H2O
Cl C
O HO
O
53. Answer (1)
CF3 – CH = CH 2
H+
+ +
CF3 – CH – CH 3 + CF 3 – CH2 – CH 2
(More stable)
–I
(Less stable Cl –
due to –I effect
of –CF3) CF 3 – CH2 – CH 2 – Cl
anti-Markovnikov
54. Answer (4)
Polysubstitution is a major drawback in Friedel Craft’s alkylation.
55. Answer (1)
DCl
CH 3 – C  C – H CH3 – C = CH
1 eq
Cl D
DI
I D
CH3 – C – CH
Cl D
Both addition follow Markownikov’s rule.
56. Answer (2)
Alkaline KMnO4 converts R with a benzylic hydrogen into benzoic acid.
C2H 5 COOH
(ii) al ka line KMn O4

+
(ii) H 3O
57. Answer (2)
OCH 3 C H3 Cl CN
> > >
(+M) (+H) (–I > +M) (–M, –I)
58. Answer (4)
CH3 group when bonded to benzene increases the electron density of benzene by +I and hyper conjugation
effects and hence makes the compound more reactive towards EAS. Cl group decreases the electron density
of benzene by –I effect, and CH3CO group strongly decreases the electron density of benzene by –I and –R
effects. Therefore, correct increasing order the given compounds towards EAS is
COCH 3 Cl CH3
< <
(III) (I) (II)
59. Answer (1)
Angle strain is not present in acyclic compounds.
60. Answer (1)
O O
AlCl3
Cl :
61. Answer (4)
Cl 2
CH3 – CH = CH 2 CH 3 – CH — CH 2
H 2O
+
Cl
+
H2O, –H
CH 3 – CH – CH2
OH Cl
62. Answer (2)
KMnO 4
CH3 – CH = CH – CH 3 2CH3COOH
OH–, 
63. Answer (1)

EtOK /EtOH
Ph Ph (X)
Cl
(CH 3COO)2Hg + H2O + NaBH4
OMDM
OH
3
4 1 Ph Product
2
1-phenylbutanol
64. Answer (4)

H
H H29°
H
120°
H H
? Angle between Hc and Hcc = 120° + 29° = 149°
65. Answer (1)
Vinyl halide and aryl halide do not give Friedel Craft’s reaction. The reactions which are possible are :
Cl
Cl Cl
AlCl3
(b) + Cl2 (excess)
dark
Cl Cl
Cl
anhyd. AlCl3
(d) + CH2 = CH — CH2 — Cl

66. Answer (4)

Peroxide generates a radical that abstracts H-atom from the C-atom adjacent to CN group to give more stable
radical
CN Peroxide  CN

[A]
[A] attacks 1-pentene to give 2° radical that picks up H-atom to give [B]
+ CN CN
[B]
67. Answer (4)

O OH
+
+
H3O
CH3 CH3
Product is aromatic
68. Answer (4)
Aniline and phenol form complex with Lewis acid.
Cl
? Highest yield in Friedel Craft reaction among given species is for chlorobenzene i.e. .
69. Answer (4)
a b c
Trans config. Trans config. Cis config.
around both around one around both
double bond double bon d double bond
Order of stability : a > b > c
Order of heat of combustion : c > b > a
70. Answer (2)
Each carbon atom is sp2 hybrid
? 3 sp2 hybrid orbitals are formed by each carbon atom
Total sp2 orbitals = 6 × 3 = 18
71. Answer (3)
H 3C CH = CH 2 H3C CH – CH 3
+
H 3O
Rearrangement .
72. Answer (3)

LiNH2 /ether –
CH CH CH
Br
HgSO4
CH3 — CH — CH(CH3)2 H2SO 4
CH3 — CH — CH(CH3)2
O == C C
CH3 CH
NaBH4
conc. H2SO 4
CH3 — CH — CH(CH3)2 
CH — OH
CH3
C(CH3) 2
+
CH3 — C CH3 — C — CH(CH3 )2
C2 H5 CH2CH3
(after Hydride shift)
73. Answer (1)
O O
O: AlCl3
+ (A)
HO
O O
Zn – Hg/HCl
H3 PO 4
HO
O O
(B)
74. Answer (4)
CH3CH == CHCH(CH3)2
+
H
H
CH3
+
CH3CH2 – CH – C
CH
Hydride
shift
CH3
+
CH3– CH2 – CH2 – C
–
CH3
Br
Br
CH3
CH3– CH2CH2 – C
CH3
75. Answer (3)
CH 3 CH 3
t
KO Bu/ 
CH3 – CH – CH – CH 3 CH 3 – CH – CH = CH 2
(ii) O3/H 2O2
OSO2CH 3
(oxidative
ozonolysis)
CH 3
CH3 – CH – COOH + HCOOH
76. Answer (1)
CH3 CH3 CH3

Br Br
HBr HBr
Br
NO2 NO2 NO2
77. Answer (4)
2+ +
Hg /H
C C OCH3 H2 O
Hydration
of alkyne
O2N
OH
CH C OCH3
O 2N
Tautomerisation
O
O2N CH2 C OCH3
Ethers are least reactive and their cleavage takes place under drastic conditions.
78. Answer (3)
(C 6H5 CO) 2
+ HBr (A)
Br
+ HBr Br (B)
Br
+ HBr (C)
Boiling point decreases with branching.

? Order of B.P. is A > C > B
79. Answer (1)
NO2 NO2
HNO3 Br2
H2SO4 Fe Br 3
Br
Mg/ ether
NO2 NO2
CO2
H3O +
MgBr
HOOC
80. Answer (1)
+ Br2
h Br +
(T = 125°C)
Br
Excess Major Minor
Bromination is highly selective, reactivity order –
3° >> 2° > 1
81. Answer (2)

O O
Br2
AlBr3, ether
Br
Ketones are meta directors.
Br2 + AlBr3  AlBr4– + Br +
O O
+ Br+ +
Br H
Arenium ion
O AlBr 4–
Br
82. Answer (1)

Br
Br
(A) : CH3–CH = CH 2 H 2O CH3 –CH–CH2
2
OH
+
Br
Br2
(R) : CH3–CH = CH 2 CH3 –CH–CH2
..
H 2O
..
CH3–CH – CH 2–Br
OH
83. Answer (4)
NO 2
conc. HNO3
conc. H2SO4

(A)
Cl2
Anhyd. AlCl3
NH2 NO 2
Fe
HCl
Cl Cl
(C) (B)
84. Answer (4)
O + O AlCl
••
3
AlCl3
O O
O O
+ O AlCl
–
3
Cl3Al O
O
O O
O O
–
O AlCl 3
Zn/Hg
HCl
OH
O
(B)
85. Answer (3)
+
H+ +
CH3 CCl 4 CH3
Br
Br–
CH3
CH3
(A)
The reaction involves the formation of 2° carbocation followed by methanide shift to give 3° carbocation. Br–
ion attacks the 3° carbocation to give the major product.
86. Answer (4)
Carbocation B is more stable as it is secondary carbocation having more number of D-hydrogens and having
greater +I effect.
? Carbocation B formed at a faster rate than carbocation A.
87. Answer (2)
Alkanes having tertiary H can be oxidised to corresponding alcohols by KMnO4.
KMnO4
2-methyl butane OH
whereas ordinary alkanes resist oxidation.
88. Answer (2)
In presence of U.V. light, free radical substitution reaction occurs, at allylic position.
Cl
Cl2
U.V.
Cl
89. Answer (2)
Partially deactivated palladised charcoal is called as Lindlar’s catalyst.
90. Answer (1)
x Alc. KOH causes elimination
x Pd / BaSO4 – Lindlar’s catalyst
x BHC is obtained by the addition reaction of Cl2 with benzene in presence of U.V.
x Thin film of polyacetylene can be used as electrode in batteries.
91. Answer (1)
KMnO4 COOH
H2SO4,  COOH
(A)
OH
KMnO4
H2O, 273 K
OH
(B)
92. Answer (1)
In the nitration of benzene using nitrating mixture, HNO3 acts as a base and H2SO4 acts as an acid to generate
NO2+ ion.
H2SO4  H  HSO4
+ + +
HO N O + H H2O N O H2O + NO2
O O
NO2 NO2
+
+ –H
+ NO2
93. Answer (3)
(C 6H 5CO) 2O2, HBr Br

kharasch effect
Br Br
CoF2
Br
94. Answer (1)
O
OH O +
+
H
H3C H3C OCH3
OCH3 –H 2O
O O
CH3 OCH 3 CH3 OCH3

Br
– +
Br
(Major)
95. Answer (2)

+
KM nO4/ H
O
2-methylpropene (A) (B)
Ozonolysis
O
2-methylpropene (A) (B)
96. Answer (4)

CH3 – CH2 – CHO (Propanaldehyde) cannot be prepared by addition of water on alkyne in the presence of
HgSO4 and H2SO4.
O
H2O
C  CH 2+ +
C CH3
Hg , H
H2O
HC  CH 2+ +
CH3 – CHO
Hg , H
O
H2O
CH3 – C  CH 2+ +
CH3 – C – CH3
Hg , H
97. Answer (1)
+
H
1, 2 methyl
shift
–
I
I
98. Answer (2)

CH3
CH2 CH3 CH3

Mo2O3
773 K, 10-20 atm
CH2 CH (Aromatisation)
CH2 CH3 (A)
99. Answer (2)

NO 2 NO 2
H 2SO 4
NO 2 NO 2
+ H


NO 2
(Major)
100. Answer (2)
CH2  C  CH  CH3
sp2 sp sp2 sp3
Hybridization of carbon 1, 2, 3 and 4 respectively are sp2, sp, sp2 and sp3
101. Answer (4)
CH2 CH3
(1) Zn/HCl
(2) Cr 2 O3 , 773 K
O 10 - 20 atm
102. Answer (2)
(i) NaNH 2
CH3 – CH = CH – Br (ii) Red hot iron
tube, 873 K
CH3
H3 C CH 3
Mesitylene
So, the correct option should be (2).

103. Answer (3)
+
OH OH2
+
H 3PO4
120°C
OH
(BH 3)2
–
H 2O 2, OH
H 2O
(P) (A)
104. Answer (3)
HBr
.
(excess)
Br
(Major product)
105. Answer (13)
Red hot Cu tube

3 H–C C–H
(Lowest molecular
weight alkyne)
(B)
(A)
H H
H
H C
H CH3 Cl(1 eq.)
Anhyd AlCl3
H H
H
(C)
Number of atoms in one plane = 13
106. Answer (03)
Given mass
Mole =
Molar mass
Given volume (at STP in L)
=
22.4
1.53 448  103


Molar mass 22.4
1.53  22.4
Molar mass = = 76.5 g mol–1
448  103
There can not be more than one chlorine atom per molecule because molar mass 76.5. One of the possible
compounds is Cl – CH2 – CH = CH2.
(i) O
Cl – CH2 – CH  CH2  3
(ii) Zn/ ACOH
 ClCH2 – CHO  HCHO
107. Answer (02)

Br
H 3C H H3C H
C CCl 4 C
+ Br2
C C
H 3C H H 3C H
Br
(+ ) P
Addition of Br2 to alkene is anti addition.

Two stereoisomers are formed in the given reaction.
108. Answer (07)
(1) Red hot Fe tube

CH  CH
873 K
(2) CO, HCl, AlCl3
CHO
All the 7-carbon-atoms in product are sp2 hybridised.

Step-3
Chapter 10
Hydrocarbons
Solutions
SECTION - A
Objective Type Questions (One option is correct)
 Alkanes (Nomenclature, Classification, Preparation, Properties)
1. Answer (4)
Br CH3
0 C
 (CH3 )2 CuLi 
(C2H5 )2 O

2. Answer (4)
Br 2/CC l4
X
HBr
X
H2 /Ni
200° C
3. Answer (3)
–
Cl—Cl + FeCl3 Cl + [FeCl4]
Cl
Cl Cl
Cl
Cl
4. Answer (2)
H H
Br 2
Me Cl Me Cl (always an optically active compound will be formed)
h or 
R-2-Chloropentane Intermediate which will

abstract Br from both sides
 Equal mixture
5. Answer (2)
SO 2Cl 2 alc. KOH
C6H5CH2CH 3 
C6H5 — CH — CH 3 C 6H 5 — CH —
— CH 2
—
Cl
6. Answer (4)
–
1, 2, 3 substrate form stable carbocation after elimination of Br
7. Answer (1)
Cl Cl
—
Cl 2
CH3 — CH CH 2
E.A.R.
CH3 — CH —
— CH 2
Cl 2/500°C
CH2 — CH CH 2
F.R.S.R
—
Cl
8. Answer (2)
Diimide (N2H2) is a very mild selective reagent which does not reduce epoxide in the given condition.
9. Answer (4)
10. Answer (4)
CH2N2 CH2I2 + Zn

11. Answer (1)

CH3 CH3
—
(i) Hg(OAc)2, H 2O
CH3 — C — CH —
— CH 2 (ii) NaBH4
CH 3 — C — CH — CH 3
—
CH3 CH3 OH
CH 2CH 3 CH 2CH 3
1. B H3/THF
*Markovnikov addition (without rearrangement) – H
2. H2O 2/OH
OH
H
12. Answer (4)
Attack of E+ on D double bond will result into the formation of most stable carbocation.
13. Answer (4)
CH3
CH 3 (i) O3 CH 3
—
— O
(ii) Zn/H2O O
H—C
H O H
—
—
O
14. Answer (2)
Br
alc. KOH
followed by NaNH2
H H
Br
SECTION - B
Objective Type Questions (One or more than one option(s) is/are correct)
1. Answer (1, 2)
Sabatier-Sanderen’s reaction forms alkene to alkane with same number of C-atoms.
Clemmenson reduction is for aldehyde and ketone to form alkane with same number of C-atoms.
2. Answer (2, 3)
Steps where one free radical is converted to another free radical are known as propagation steps.
3. Answer (2, 3, 4)
Electrolysis
H3C – COOK + CH3 – CH 2 – COOK CH 3 – CH 3 + CH 3 – CH 2 – CH 3 + CH 3 – CH 2 – CH 2 – CH 3
4. Answer (3, 4)
H2O
R – COOK R–R
electrolysis
Na
R–X R–R
ether
5. Answer (1, 2, 4)
Only in neopentane all H’s are equivalent. Therefore, it will give only one monochloro derivative. Other alkane
will give more than one monochloro derivatives.
6. Answer (2, 3, 4)
CH2N2 cannot change unsaturation.
7. Answer (1, 4)
Both can absorb 3 mole H2 to form a straight alkanes.
8. Answer (1, 2)
Hydrogenation follows true radical mechanism.

9. Answer (2, 3)
HCN is weak acid and cannot attack to alkenes.

10. Answer (1, 2, 3)
R O /Zn–H2O R
C = CH – R 3 C = O + R – CHO
R R
O3/H2O R
C = O + R – COOH
R
O 3/Zn – H2O CHO

CHO CH2 = CH 2 2HCHO
,
O 3 / H2 O COOH 2HCOOH
COOH
11. Answer (2, 3, 4)
O3/H2O COOH
HC CH +
H COOH
KMnO4/O H /H2O(c old)
–
CHO
or CHO
SeO2
or
O3/Zn–H2 O
12. Answer (2, 3, 4)
No elimination is possible in
13. Answer (1, 3)

As MeO – group is ortho-para director the probable V-complexes in electrophilic substitution of anisole are
OMe
ortho attack
 
of E
OMe E
H
OMe
para attack
of electrophile

H
O2N
14. Answer (1, 3)
O
Ac2O and CH3 – C – Cl will generate acylcarbocation with Lewis acid and hence acyl carbocation will give
acetophenone with benzene.
15. Answer (2, 4)
+
Rearrangement 
CH2 = CH – CH2
SECTION - C
Linked Comprehension Type Questions
Comprehension-I
1. Answer (1)
CH3
CH3 – CH – CH3
9 1
%1º product =  100  64%
9 1 5
%3º Product = 100 – 64 = 36%
2. Answer (2)
Cl2/h
Its % formation is maximum
Cl
Br2/h
Br due to formation of most stable radical
3. Answer (1)
Br
Br2
h
Comprehension-II
1. Answer (2)
Farnesene has two stereocenters hence-four stereoisomers are possible.
2. Answer (1)
ICl  I  Cl , Cl– attacks on more stable carbocation.
3. Answer (1)
C=C are not hydrogenated under the presence of Ni2B or Lindlar’s catalyst.
Comprehension-III
1. Answer (3)
Oxymercuration-demercuration gives alcohol without rearrangement.
2. Answer (1)
Conjugate base of HBr is a strong nucleophile hence it interferes in the reaction.
3. Answer (1)
Ring expansion.
Comprehension-IV
1. Answer (4)
CH3
H OH
H = trans-2-methylcyclo pentanol
2. Answer (1)
Hydroboration step of the reaction proceeds through Markovnikov’s addition, but the overall reaction gives
anti-Markovnikov’s product.
3. Answer (1)
BH3 is a Lewis acid (electrophile) due to incomplete octet.
SECTION - D
Matrix-Match Type Questions
1. Answer A(r), B(r), C(s), D(p)
CH3
(1) CH3
CH3 CH3
(2)
CH3 — C — CH3
(3) , CH3 — CH — CH3 ,
(1) (2)
(4) CH3
(only 1)
2. Answer A(r), B(p), C(s), D(q)
Oxymercuration demercuration follow Markovnikov’s addition of H 2 O without forming carbocation
Alkoxymercuration forms ethers without forming carbocation.
Acidified hydrolysis follows carbocation mechanism hydroboration forms anti-Markovnikov's product.
3. Answer A(p, s, t), B(p, r, s, t), C(s, t), D(r, s, t)
In carbocations, rearrangements are possible to gain more stability. Optical isomerism is observed due to
presence of chirality.
4. Answer A(p, q, r), B(p, r, s), C(p, q), D(p, r, s)
In Cl, –I effect predomination over + R effect
–OCH3 is a group of +R and activating towards substitution electrophilic reaction
–NO2 is a group of –R effect and deactivating towards substitution electrophilic reaction
–OH is a group of +R effect and activating towards substitution electrophilic reaction
SECTION - E
Assertion-Reason Type Questions
1. Answer (1)
Surface area deceases with increase in branching
2. Answer (4)
Due to presence of electron withdrawing group vinyl chloride is less reactive than ethylene.
3. Answer (1)
Question is self explanatory.
4. Answer (4)
Alkynes are less reactive than alkenes towards electrophilic addition reactions.
5. Answer (2)
1st step is according to Markovnikov’s rule.
6. Answer (3)
Due to 50% s-character of triple bonded carbon hydrogen becomes acidic and C — H bond is formed by
sp-s linkage.
7. Answer (2)
Nitro group is highly deactivating group.
8. Answer (4)
Multiple alkylation is present in Friedel-Crafts alkylation not in acylation.
9. Answer (2)
10. Answer (2)
& are position isomers
SECTION - F
Integer Answer Type Questions
1. Answer (3)
2. Answer (8)
3. Answer (6)
Number of H in CnH2n  2  Number of H in compound  Number of x

U.F. 
2
4. Answer (4)
1-butene, isobutene & cis-trans -2-butene
5. Answer (5)
Reactions a, b, c, d, e are example of regioselective.
6. Answer (7)
CH 2 O
i. O3
+ H C H
ii . H 2O/Zn
O
M = 56
M
7
8
7. Answer (6)
8. Answer (3)
9. Answer (45)
O
—
—
B is CH 3 — C — CH 2CH 3
H H
—
C is O == C — C == O &
H
—
D is CH 3 — C == O
Total sum = 27 = (B + C + D)
CH3
Fe,  CH3Cl
HC  CH  
anhyd.AlCl3
R = 18
10. Answer (4)
Quinoline react slower than benzene.
SECTION - G
Previous Years Questions
1. Answer (B)
2. Answer (D)
Br
CH2—CH2—CH2—CH3
NH2
CH3—CH2—CC—H CH3—CH2—CC CH 3—CH2—CC—CH2—CH 2—CH2—CH 3
3-octyne
3. Answer (C)
COOH COOH
HNO3/H2SO4
HO HO
NO2
OCH3 HNO3/H2SO4 OCH3
H3C H3C NO2
O O NO2
C HNO3/H2SO4
C
O O
4. Answer (B)
H (sp) H
C=C=C
H H
(sp2) (sp2)
(Allene)
5. Answer (A)
Ozonolysis produces CH3CHO and CH3–CH(CHO)2.
6. Answer (B)
As branching increases boiling point decreases, so order of boiling point is III > II > I.
7. Answer (B)
It is a case of Birch reduction. Alkynes on reaction with alkali metal in liq. NH3 gives trans-alkene. But terminal
alkynes do not get reduced.
NaNH 2
Na
liq. NH3
8. Answer (B, D)
X H3C CH3
H3C CH3
X C
C
H H H HY
Y
When X = H & Y = C2H5
H3C CH3
H C
2
C C2H5
H 1 H
2, 2- dimethyl butane
When X = CH3 and Y = CH3
H3C CH3
C2
4CH3
C CH3
H 3 H 1
2, 2-dimethyl butane
9. Answer (D)
CH3
CH2 1 equiv. HBr
H2C H
+
H3C 
 Br
–
Br
(Major)
10. Answer (B, C, D)
Br
+
NaOEt
–
AlCl3 + 1, 2 H +
Shift
Cl
+
H +
BF3 1, 2 H– +
+
O–H Shift
H
11. Answer (B, D)

HC
3 H CH3 CH3
(i) C=C (ii) C=C
H CH 3
H Cis H
Trans
Br2
Br2 /CHCl3
CH3 CH3
CH CH
3 3
H Br Br H
H Br Br H +
Br H H Br
+
H Br Br H CH3 CH3
CH CH
3 3
O P
Meso (M and N) Pair of enantiomers
Cis anti Racemic
M and N are meso (identical)
O and P are pair of enantiomers
(B) Bromination proceeds through anti addition.
(D) (M and O) and (N and P) are two pairs of diastereomer.
12. Answer (B, D)
Br
EtO
(A) (Anti Aromatic)
H
Me
(i) Alc. KOH
(B) Br Br (ii) NaNH 2 Me — C º CH
Red hot Fe tube, 873 K
Cl
Cl Cl
UV
(C) + 3Cl2
500 K Cl Cl
Cl
H
(D) MeO
+ MeOH
13. Answer (B, C)

Me
Zn
(A) CH3—CH == CH2
Br Br
NaOH–CaO
(B) COOH 
Zn
(C) Cl +
H
2 Electrolysis
(D) COONa + 2H2O + 2CO2 + H2 + 2NaOH
14. Answer (B, C)
X Pd-C/Quinoline/H2
*
R
(P)
(ii) KMnO4/H2SO4/
* COOH
COOH
COOH
(Q)
15. Answer (D)

16. Answer (B)
Solution of Q. Nos. 15 and 16
O (i) NaBH4 OH
H3C 2+ + H3C H3C
Hg /H3O (ii) dil H
+
H3C C – C C–H H3C C – C H3C C – C – H

H3C H3C CH3 H3C CH3
H3C H H3C H 
–H   H
C – C – CH3 H3C C – C
H3C CH3 H3C CH3
(i) O3
H3C CH3 CH3
(ii) Zn–H2O
C C 2 C O
H3C CH3 CH3
17. Answer (A)
NaNH2 CH3 CH2 I
H C–Na+ C
+ – (1 eq) + –
HO Na O Na O
CH3 I
CH3
H2
CH3 O
O Lindlar's
H H catalyst
18. Answer (C)

1. NaNH2 (2 eq ) O
2. OH
Br
H +
3. H3O (mild)
4. H2, Pd/C
5. CrO3
19. Answer (C)
OH
Pd-BaSO4 i. B2H6
C8H6
H2 ii. H2O2, NaOH, H2O
X
20. Answer (D)
O
H2O
C8H6
HgSO4
H2SO4
i. Et MgBr, H2O
+
ii. H , Heat
21. Answer (A)
H – C H(CH3)2 HC – CH3
CH 3
H – C H2Ph CH2 – Ph
Benzyl radical
H – CH = CH2 o xCH = CH2

H – C { CH o xC { CH
Order of stability of free radical
Q>P>R>S
1
Stability of free radical v
Bond energy
? Order of bond energy :

S>R>P>Q
22. Answer (D)
(1) Cl2 o 2Clx (Initiation step) 'H = 58 kcal/mol
(2) CH4 + Clx o xCH3 + HCl 
xCH
 Propagation step
(3) 3 + Cl2 o CH3Cl + Clx 
Step (1) o Endothermic (bond breaking)
Step (2) o 'H = 105 – 103
= 2 kcal/mol (Endothermic)
Step (3) o 'H = 58 – 85
= –27 kcal/mol (Exothermic)
For complete reaction,
light
CH4 (g)  Cl2 (g)  CH3 Cl(g)  HCl(g)
'H = 58 + 105 – 85 – 103

= –25 kcal/mol
23. Answer (A)
NaOEt
(P) Cl
(Q) ONa + Et-Br OEt
(1) Hg(OAc)2 OH
(R)
(2) NaBH4
(1) BH3
(S) (2) H2O2/NaOH
OH
24. Answer (4)
Aqueous dilute
OH
+
H H KMnO4 (excess)
Heat
HO OH
HO
(P) OH
25. Answer (6)
(i) H2, Pd-BaSO4, quinoline
HO
(ii) dil. KMnO4 (excess)
OH
273 K
HO OH
OH
OH
26. Answer (12)
O O
O O
+ +
OH OH OH OH
N N N N
2. NH 2OH (–) (–)

(–) (–)
(excess)
N N N N
+ +
OH OH OH OH
(P)
The total number of atoms having sp2 hybridisation in the major product (P) = 12
This includes 4 C-atoms, 4 N-atoms and 4 O-atoms.


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Step-1

I > II > III

Correct IUPAC name is 3, 3-Dimethylbut-1-yne.

Most reactive towards ESR.

C  C – CH 2CH3 C – CH2 – CH2CH3

13. Answer (1)

26. Answer (3)

28. Sulphur trioxide acts as an electrophile.

29. (A) = (B) =

sp3 > sp2 > sp

The decreasing order of bond enthalpies is,

CH3Cl + 2Na + ClCH3  CH3 – CH3 + 2NaCl

(ii) CH3COOH + NaOH o CH3COO–Na+ + H2O

Contains less number

Three products or three monochloro isomeric n-pentane can be obtained i.e.,

Increasing hyperconjugative structures, hence, higher stability

 Alkanes (Nomenclature, Classification, Preparation, Properties)

Butane can form n-butane and isobutane.

Due to largest surface area.

Compound Boiling point

2,2-dimethyl butane 50°C

(CH3)3 CMgCl + D2O o (CH3)3CD + MgODCl

 Alkenes (Nomenclature, Classification, Preparation, Properties)

It contains only primary hydrogen.

CH3  CH2  CH2  CH  CH2 CH3 – CH  CH – CH2 –CH3

with respect to presence of alkyl groups.

C4H8  Br2  C4H8Br2

∵ 8 g Br2 reacts with 2.8 g alkene

13. Answer (2)

It is an unsaturated acid hence shows addition with bromine.

17. Answer (3)

CH3 CH3 CH3 CH3

23. Answer (3)

 Alkynes (Nomenclature, Classification, Preparation, Properties)

(Radical anion) – a reactive intermediate

 Aromatic Hydrocarbons (Preparation, Properties)

> > >

30. Answer (2)

CH3 — CH — CH2 — CHCl2 Cl — CH2 — CH — CH2CH3

Cl — CH2 — C(Cl) — CH2CH3 Cl — CH2 — CH — CH(Cl) — CH3

Cl — CH2 — CH — CH2CH2Cl CH3 — C(Cl) — CHCl — CH3

CH3 — C(Cl) — CH2CH2Cl CH3 — CH — CH(Cl) — CH2Cl

35. Answer (06)

Previous Years Questions

42. Answer (4)

Contain 6Se– in complete conjugation and are aromatic.

is anti-aromatic as it has 4Se– in complete conjugation.

43. Answer (2)

44. Answer (1)

? Major product will be formed as per activating group.

? Product formed is O2N

is aromatic as it has 2Se– in complete conjugation

and are antiaromatic.

47. Answer (1)

50. Answer (3)

Alkaline KMnO4 converts R with a benzylic hydrogen into benzoic acid.

(ii) al ka line KMn O4

57. Answer (2)

> > >

(+M) (+H) (–I > +M) (–M, –I)

58. Answer (4)

59. Answer (1)

Angle strain is not present in acyclic compounds.

(ii) CH3COOH + NaOH o CH3COO–Na+ + H2O