ALKANE, ALKENE, ALKYNES & DIENES

Single answer type questions:

1. Which is incorrect product?

(A) H3C CH3

CH3  C  C  CH3 
Na / Liq.NH3
C C
H (cis) H
(B) H3C CH3
CH3  C  C  CH3 
 H2
Pd / BaSO4 C C
H (cis) H
(C) H CH3
CH3 CH3
H Br Br H

Br2
 
Br H H Br
H CH3
CH3 CH3
cis-But-2-ene
( ) -2, 3-Dibromobutane

(D) CH3
H CH3
H Br

Br2

H Br
H3C H
CH3
trans-But-2-ene
Meso -2, 3-dibromobutane

2. Addition of IBr to 2-methylbut-2-ene would form

(A) 2-Bromo-3-iodobutane (B)2-Bromo-2-iodobutane
(C)2-Bromo-3-iodo-2-methylbutane (D)2-Iodo-3-bromo-2-methylbutane

3. The major product of the following reaction would be

4. Identify the correct statement about the reaction;

OCOCH3
H Ph

H Ph
D

A) It is a syn elimination reaction and gives cis alkene

B) It is an anti elimination reaction and gives trans alkene
C) It is a syn elimination reaction and gives trans alkene

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 D) The product does not contain deuterium
5. Which of the following is having highest heat of
hydrogenation?
A) B) C) D)

6. CH3

Moist Ag 2O
+ CH3
N I Heat
CH3
Product, the main product is:
A) CH3 B) CH3

CH3 CH3
N N

CH3 CH3
C) D) CH2
CH3
CH3
N
CH3
N CH3

7. H3C COOK

The main product in the Kolbe’s electrolysis of H3C COOK is

A) B) C) D)

8. O
O C CH3

H Ph 
Products
H Ph 
 5000 C 
D

A) One of the products will give a racemic mixture with Br2 / CCl4

B) One of the products will give a meso product with Br2 / CCl4

C) Reaction is an example of anti-elimination

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 D) Entropy of reaction is negative
9. In which of the following sp, and hybridized carbon atoms are not in

1 : 2 : 3 ratio
A) 3-methyl-1,3-pentadiene B) 2-methyl-1,3-pentadiene
C) Both A and B D) 2-methyl-2,3-pentadiene
10 .

Product (P) and (Q) respectively

A) B)

C) D)

11.

A is
A)

B)

C)

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 D)

12. Which alkyne will not give 3-ethylhexane on catalytic hydrogenation

?
A)

B)

C)

D)

13. Which starting material should be used to produce the compound shown
below?

A) B)

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 C) D)

14. alc.KOH
CH3  CH 2  CH  CH3   X  major  
Br
  CCl  Product
2
| 4
Br
What is the final product of the reaction ?
A) Racemic mixture B) Meso compound
C) Diastereomers D) Optically active
15. Which of the species shown below is the most stable form of
the intermediate in the electrophilic addition of in water to
cyclohexene to form a halohydrin ?
A) B) C) D)

16. Cl ,5000 C
CH 2  CH  CH 3 
2 A . The product A is

A) B)

C) D)

17. The major product of the following reaction is

A) B) C) D)
Both (A) and
(B)

18. The major product in the dehydrohalogenation of 2-Bromo-3, 3-

dimethyl-butane is
A) 3, 3-dimethyl but-1-ene B) 2, 3-dimethylbut-1-ene
C) 2, 3-dimethyl but-2-ene D) 4-methylpent-2-ene
19.
Find the product X.

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 A) B) C) D)
Both B and C

20. 2- Hexyne gives trans 2- hexene on treatment with

A) B) C) D)
Li/ Pd/Ba Li
21. Electrophilic addition occurs on
A) B) C) D) Both A and B
22. Arrange reactivity of given compounds in decreasing order for electrophilic
additionreaction:
1) Ethene 2) 1-Butene 3) 2,3-Dimethyl-2-butene 4) 2-
Butene
A) 2,3,4,1 B) 3,4,2,1 C) 3,2,1,4 D) 4,3,2,1
23. Arrange the following halogenating agents in order of decreasing selectivity in
free radical reactions:
1) NBS 2) NCS 3) Cl2 4) F2
A) 4,3,2,1 B) 1,2,3,4 C) 2,1,3,4 D) 1,2,4,3
24.
Bromination of in presence of sun light gives the product
A) with retention of configuration B) with invertion of configuration
C) with a racemic mixture D) which has no chiral carbon
25.
The major product in these addition
A) B) C) D)

26. I Cl
CH3  CH  CH 2   The major product

A) B) C) D)

27. Which of the following reaction takes place by formation and rearrangement
of carbocation

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 (i) Hg(OAc)2, H2O (i) BH3
(A) R CH CH CH2 (B) R CH CH CH2
(ii) NaBH4 (ii) H2O2
CH3 CH3

(D) (i) HNO2

(C) CH3 C CH2 HX
(ii)
CH3 OH NH 2
2
Zn  Hg
28. CH  CH Hg
dil H 2 SO4
 A 
HCl
 B; B is
a) C2 H 4 b) C4 H 6 c) C2 H 6 d) C6 H 6
29. In the given reaction C6H5  CH  CH  CH3  ICl   A  A is

a) Cl b) C6 H5  CHI  CHCl  CH3

|
C6H5  CH  CHI  CH3
c) C6 H5  CHCl  CHCl  CH3 d) No reaction is possible
30. Identify the major product P in the in the following reaction.

d) All are formed in equal amount

31.

Indentify P.

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32. Consider the following reaction

X is :

Hg 2 , H 2 SO4
A
33. H 2O , A is
O
O
O

O
a) b) c) d)

HO  CH 2  CH 2  C  CH 
1eq NH
34. CH CH  X 
2
3 2
a) CH3  CH 2  O  CH 2  CH 2  C  CH b) HO  CH 2  CH 2  C  C  CH 2  CH 3

c) CH3  CH 2  OCH 2  CH 2  C  C  CH 2  CH3 d) O

Ph
CH -P Ph
Ph
CH3
O A
35. , then A is

a) b) c) d)

H Cl
H 2O 2
A Major
36. then A is
CH2 -Cl
Cl Cl

a) Cl b) c) d)

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37. C6 H5  CH  CH 2 
Br
 A 
2 Threeeqivalent
NaNH 2
 B 
CH I
 C Compound ‘C’ in the sequence is.
3

CH3 C  C  CH 3 C  CI CH  CH 2

a) b) c) d)

38. Which alkyne will give 3-ethylhexane on catalytic hydorgenaion?

a) b) c) d) All of these

39. Which of the following statements best explain the greater acidity of terminal
alkynes  RC  CH  compared with monosubstituted alkenes  RCH  CH 2  ?
a) The sp-hybridized carbon atoms of the alkynes are less electronegative than
the sp2 carbons of the alkene.
b) The two  bonds of the alkyne are better able to stabilize the negative
charge of the anion by resonance.
c) The sp-hybridized carbons of the alkyne are more electronegative than the
sp2 carbon of the alkene.
d) The question is incorrect - alkenes are more acidic than alkynes.
40

 
Re d hot
Iron tube X . X is

CH 3 CH 3
CH  CH  CH 2

a) b) c) d)
CH 3 CH3 CH 3 CH 3

 3
41. X 
1O
 2 H O / H 
2
 CH 3  CH 2  COOH  HOOC  CH 2  CH 2  COOH  HCOOH
a) CH3  CH2  C  C   CH 2 2  C  CH b) CH3  C  C   CH 2 3  C  CH
c) CH3  CH 2  C  C  CH 2  C  CH d) HC  C   CH 2 4  C  CH

Page No - 9 -
42.

dil H 2 SO4 / HgSO4
 X. Xis
OH

a) OH b)
O

c) d)

43. Acetylene reacts with Cl2 / NaOH to produce

a) 1, 2 – dicholo ethene b) 1, 1 – dibromo ethene
c)   choloro ethane d) dicholo ethyne
H CH3

44. In the given reaction C = C 

Br2 / CCl4
 X (X) will be

CH3 H

a) meso – 2, 3 – dibromobutane
b) d -2, 3 – dibromo butane
c) 1:1 mixture of d-and l-2, 3- dibromo butane
d) 2 :1 mixture of d- and l-2, 3- dibromo butane
45. What is the final product, C, of the following reaction sequence ?

H 
1. NaNH 2
2.CH 3CH 2 Br
A
3 
A  B
Na , NH liq .

B 
Br2
CH 2Cl2
C

Br
Br Br
a) b)

Br

Br Br

c) d)

NH2 Br

Page No - 10 -
46. An alkane with formula C6 H14 ( A) reacts with chlorine to yield three
compounds with the formula C6 H13Cl ; ‘B’, ‘C’ and ‘D’. Of these, only ‘C’ and ‘D’
undergoes dehydrohalogenation with NaOC2 H5 in C2 H 5OH to produce same
alkene ‘E’  C6 H12  . Hydrogenation of ‘E’ produce ‘A’. Treating ‘E’ with HCl
produce ‘F’ isomer of B,C and D. Treating ‘F’ with Zn & CH 3COOH gives
compound ‘G’ which is isomer of ‘A’. Then structures of A and G are
(a) n-hexane & isohexane (b) Isohexane & neohexane
(c) neohexane & 3-ethyl butane (d) neohexane & 2,3 –dimethyl butane
47. Compounds ‘I’ and ‘J’ both have same M.F. i.e. C7 H14 . Both are optically active
and both rotate the plane-polarized light in the same direction. On catalytic
hydrogenation ‘I’ and ‘J’ yields same compound ‘K’  C7 H16  which is optically
active. Then the structure of ‘K’ is
(a) 2,3 – dimethyl pentane (b) neo-heptane
(c) 3 – methyl hexane (d) isoheptane
48. Cyclopentane reacts with excess Cl2 at a high temperature, how many
dichloro cyclopentanes are formed
(A) 3 (B) 4 (C) 5 (D) 7
49.
CH 3  CH  CH 2  CH  CH 2  CH 2  CH 3  
Cr2O3 / Al2O3
8000 C
 X . Find the product 'X'

CH 3 CH 3
CH 3 CH 3 CH 3 CH 3

CH 3  C  C  CH 2  CH 3 CH 3  C  CH 2  C  CH 3
CH 3 CH 3 CH 3 CH 3
A) (B)
CH 3
CH 3
CH
CH 3
H 3C CH 3
(C) (D)


alcKOH  X major
CH2Br 
 
50. Find the product ‘X’.

CH 2

(A) (B)

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 (C) (D) Both B and C
51. An alkane of molecular formula C8 H18 , on monochlorination yields single
isomer with molecular formula C8 H17Cl. The structure of alkane is ---
CH 3 CH 3
C2 H 5
A) CH 3  CH  CH  CH 3 B) CH 3  C  CH 2  CH  CH 3
C2 H 5 CH 3

CH 3 CH 3 CH 3 CH 3
C) CH 3  C  C  CH 3 D) CH 3  CH  CH  CH  CH 3
CH 3 CH 3 CH 3
52. Which of the following cycloalkanes involve maximum torstonal strain?
a) cyclopropane b) cyclobutane c) cyclopentane d) cyclohexane
53. The intermediate during addition of HCl to propene in presence of H2O2 is
 
(A) CH3  C H  CH 2Cl (B) CH3  C H  CH 3


CH3  C H 2  C H 2
(C) CH3  C H 2  C H 2 (D) |

Cl
54. Identify ‘F’ in the following reaction sequence
C

Cl2
hv
A 
alc. KOH
 D 
NBS
 E  F
aq. NaOH

B 
Na
C
O
(A) (B)
Br

(C) (D) O
O

55.

The end product Y would be

Page No - 12 -
 CH3 CH2

(A) (B)

CH3

(C)
(D) none

56. A is

Me OH OH O
(a) C CH2 (b)
Me
Me OH
(c) CH CH (d)
Me OH

57. ‘Sulpholane’ is an industrial solvent. The reaction sequence of its preparation

is given below
1, 3-butadiene + SO2   Addition product   Sulpholane
o
100 C H / Ni 2

The structure of sulpholane is

(A) (B)
S S
O O O
(C) H2C CH CH2CH3 (D) H3C HC CH CH3
S S
O O O O

58. In the oxymercuration – demercuration of the following compound

CH3
H2C CH CH CH2CH2CH2OH 
(CH3COO)2 Hg
NaBH
 Pr oducts
4

The major product is expected to be

(A) H3C O (B) O CH3

H3 C
CH3
(C) O (D) H3C O CH3

H3C CH3

59. Which of the following reactions will produce acetaldehyde as one of the
products?

Page No - 13 -
 O /H O/Zn
(I) CH  CH  CH  CH 
2
3 2
2 2
O /H O/Zn
 CH  CH 
3 2
3
(II)
 2
H aq/Hg
(III) CH  CH  ...
OH
| 
H / O /H O/Zn
(IV) C H CH .CH  CH  .... 
6 5 2
3 2
3
....
(A) I, II, III (B) II, III, IV
(C) I, II, III, IV (D) I, II, III
60. Match the following reactions with the corresponding reaction intermediates
List I List II
alc.KOH /  1. Transition
(I) CF3  CHCl2 CF2  CCl2
state
(II) CH 2  CH  CH3 
SO2Cl2/ h
CH 2  CH  CH 2Cl 2. Carbocation
alc.KOH / 
(III) CH3  CH2 Br  CH 2  CH 2 3. Carbanion
alc.KOH / 
(IV) (CH3 )3 C  Br  (CH3 )2 C  CH 2 4. Free radical
(I) (II) (III) (IV)
(A) 3 2 1 4
(B) 3 4 1 1
(C) 2 4 3 1
(D) 3 4 1 2
61.
..
OH
.. H+/H2O
48. ? (X)
CH CH2
X is
..
(A) O CH CH2 CHO
.. (B) CH2

O
O
(C) (D)
CH3
62.

x is the Hoffmann product, y is the 1, 2 – shift product and z is the ring

expansion product.
The stability of these three alkenes follows.
(A) x  y  z (B) x  y  z (C) z  x  y (D) z  x  y

Page No - 14 -
63. Which of the following reaction has zero activation energy
  
(A) CH4 + Cl 
 CH 3 + HCl (B) Cl2 
 2 Cl
   
 CH3  CH3
(C) CH 3 + CH 3  (D) C H 3 + Cl  Cl 
 CH3  Cl + Cl

64. A is
O

(A) NO 2 C CH2 OCH 3

OH

(B) NO 2 C CH OCH 3

(C) NO 2 CH2 C OCH3

OH

(D) NO 2 CH CH OCH 3

65. The number of possible enantiomer pairs that can be produced during
monochlorination of 2-methylbutane is
(A) 2 (B) 3
(C) 4 (D) 1
66. cis-2- Butene 
HOBr

CH3 CH3
H OH H OH
(A) (B)
H Br Br H
CH3 CH3
CH3 CH3
H3C OH H3C Br
(C) (D)
Br H HO H
H H

67.

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 (B)
(A)
CH3

(C) (D) CH3

CH3

68. Which of the following compounds on hydrolysis gives propyne ?

(A) CaC2 (B) Mg2C3
(C) Al4C3 (D) Cu2Cl2
69. An isomer of C5H12 gives total six isomeric products on monochlorination.
Calculate the percentage yield of the primary monochloride which is chiral.
Consider the following relative reactivity of C – H bonds for chlorination.

Degree of C – 10 CH 20 30
H CH CH
Relative 1 3 5
reactivity for
chlorination
(A) 26.8% (B) 25%
(C) 30% (D) 50%
70. Alkanes are less reactive or unreactive because
(A) they have non polar bonds (B) they have gaseous state
(C) they have lower bond energy (D) their m.p. and b.p. are very high
71. In which case the reaction is most exothermic with H2/Ni

(A) (B)

(C) (D)

72.

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 Br Br
(A)
(B)
CH3
Br CH3
(C) (D) Br

73.
Identify the product ?
(A) C C
(B) H – C  C – H
(C)
(D) C C K

74. The product of the following I and II sequence are related as

(i) H2/Pd/CaCO3 (ii) Br2/CCl4
?
(I)
CH3 C C CH3
(II) (i) Br2(1 eq.)/ CCl4 (ii) H2 / Pd
?
(A) Diastereomers (B) Identical
(C) Enantiomers (D) Geometrical isomers

75.
Identify the product ?

(A) C C CH3 (B) HO C C CH3

HO OH OH
H O
OH

(C) C C CH3 (D) C C CH3

OH OH

Page No - 17 -
76. What is the number of Stereoisomer/s of major product formed in the
following reaction ?
Ph
CH3 Cl
CH3 H
alc. KOH (excess)
CH3 H (-2HCl)
CH3 Cl
Ph
(A) 1 (B) 2
(C) 3 (D) 4

77.
which statements is/are correct about photochemical chlorination of the
above compound
(A) The major product will have chiral carbon atom and therefore optically
active
(B) The intermediate free radical of the major product is resonance stabilized
(C) The intermediate free radical is tertiary for major product
(D) The intermediate free radical is planar, and stabilized by only
hyperconjugation.
78. In the reaction, CH3 – CH2 – CHX – CH3  CH3 – CH2 – CH = CH2
The percentage of 1-ene increases for given X in the order.

A) Br < SMe 2 < NMe 3 B) Br < N Me3 < SMe 2
C) SMe 2 < NMe 3 < Br D) SMe 2 < Br < NMe 3
79. For the given reaction the correct statement is
(x) (y) (z) (w)
X2/h
H3C CH2 CH2 CH3
Mono halogenation

Relative reactivity of Total number of Total number of

C–H Monochloro fractions obtained
isomers on distillation
A) x>y>z>w 6 6
B) y>x>z>w 4 4
C) z>y>w>x 4 6
D) y>z>x>w 6 4
80. CH3
I  Br
Cl CH2 CH CH C OMe  
Addition
 Addition product (P)
CH3
(trans-isomer)

where P is

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 (A) CH3
Cl CH2 CH CH C OMe (meso-form)
I Br CH3
(B) CH3
Cl CH2 CH CH C OMe (racemic mixture)
I Br CH3
(C) CH3
Cl CH2 CH CH C OMe (optically active mixture
of two diastereomers)
I CH3 Br
(D) CH3
Cl CH2 CH CH C OMe (optically active mixture
of two diastereomers)
Br CH3 I
81. Cis – stilbene   A 
MMPP
CH 2Cl2
  B  

PPh3
 C 
(I) (II)
Relation ship between (I) & (II) is
a) Enantiomers b) diastereomers
c) Meso compound d) Identical compounds
82. An Alkane with least boiling point is

a) b) c) d)

83. What is not correct about E1CB reaction?

(A) Mechanism is followed when substrate is having excessive acidic proton
while leaving group is a bad leaving group
(B) the rds is unimolecular and the intermediate is carbanionic
(C) the overall order of reaction is one
(D) the rate law of the reaction is as follows:
[S]2
Rate   , where S is the substrate and B– is the base
[B ]
84. The product from the reaction of 1- pentene with Cl2 in H2O is named :
a) 1 – chloro -2 – pentanol b) 2 – chloro - 2 – pentanol
c) 1 – chloro – 1 – pentanol d) 2 – chloro – 1 – pentanol

85. The reaction sequence will yield

a) A pair of products that are enantiomers

b) A single product that is optically active
c) A pair of products that are diasteromers
d) A pair of product which is meso

Page No - 19 -
 decay
86. CH3  C  C  T   A   B intermediate   C
spon tan eous decomposition C6 H 6

choose incorrect statement

a) Intermediate is a carbocation.
b) ‘C’ is phenyl allene
c) ‘C’ gives reaction with H2O, HgSO4 , H2SO4 at 60C
d) degrees of unsaturation in ‘C’ is ‘6’.
87. Consider the following reaction sequenes

The products A and B are respectively

a) PhCOCH3 and PhCH2CHO b) PhCH2CHO and PhCH2CHO
c) PhCH2CHO and PhCOCH3 d) PhCOCH3 and PhCOCH3

88.
O
(B) C CH3
(A) CH2 C H
O

(C) CH2COOH
(D) None of these

89. An organic compound C6H8 (molecular formula) on reductive ozonolysis given

2 moles of CHOCH2CHO. The possible structure will be

(A) (B)
CH3
CH2
(C) H3C (D)
H3C

90. An alkene on reductive ozonolysis produces glyoxal (CHO – CHO) and

methanal. The probable structure of alkene is
(A) CH3 – CH = CH – CH = CH2 (B) CH2 = CH – CH = CH2
(C) CH3 – C  C – CH3 (D) CH2 = CH – C  CH

Page No - 20 -
91. Tertiary amine oxide in which one of the alkyl group contains   hydrogen on
heating to 423-473 K eliminates a molecule of dimethyl hydroxylamine to give
an Alkene. This reaction is known as Cope-Elimination.
What is the major-product in the following reaction :
O
+ NMe
D 2

H
D
D D
D D
(A) (B)
D

(C)
(D) Both (A) and (B) in almost equal proportion
92. Find the product of the following reaction
R R

CH2
R O
A) R O B) R
and H3C CH2 R
R R
O R
C) R D) R
and H2C CHO R CH2
R R
R
O
93.

H (i) t-BuOK /  (i) (CF 3COO) 2Hg / H 2O
(A) -
(B)
(ii) D 2/Ni (1eq) (ii) NaBH 4, OH
Br

O 2N
A and B respectively are
18
OH H
O 2N C C ; O 2N C C
A)
D D D D

18
H HO

B) O 2N C C ; O 2N C C

D D D D

Page No - 21 -
 18
H HO

C) O 2N C C ; O 2N C C

D D D D
18
H HO

D) O 2N C C ; O 2N C C

D D D D

94.

The final product mixture contains

(A) CH3CHO + CH3COCH3 (B) 2CH3CHO + CH3COCH3 + HCHO
(C) 2CH3CHO + HCHO (D) CH3CHO + CH3COCH3 + 2HCHO
95. Which of the following reaction takes place by formation and rearrangement
of carbocation
(i) Hg(OAc)2, H2O (i) BH3
(A) R CH CH CH2 (B) R CH CH CH2
(ii) NaBH4 (ii) H2O2
CH3 CH3

(D) (i) HNO2

(C) CH3 C CH2 HX
(ii)
CH3 OH NH 2
96. The set of reagents that needed to carry out the following conversion are
CH3  CH 2  C  CH  CH3  CH 2  CH 2  CHO
A) H2O / HgSO4 / H2 SO4 B) B2 H 6 / THF , H 2O2 / OH 
C) H 2O / H  D) Hg (OAC)2 , H2O, NaBH4
97. 2-hexyne gives trans-2-hexene on treatment with
A) Li / NH3 B) Pd / BaSO4 C) LiAlH 4 D) Pt / H 2

98. The addition of HBr to predominantly gives

Br
CH CH3 CH CH2 CH2 CH2Br NO2
O2N NO2 O2N NO2 NO2 NO2

A) B) C) D)
Br O2N NO2
NO2 NO2 NO2
99.

Page No - 22 -
 X is
O
H Cl
(A) (B)
O O
Cl OH
O O

(C) (D)
O Cl O Cl

100. I-

Major Product

(A) (B)
D

(C) (D) H2C = CH2

D
H

101. The major product of the following reaction is

O
D NMe2
H3C H

 
D
D

(A) H3C D

(B) H3C D

(C) H3C

(D) Both (A) and (B) in almost equal proportions.

Page No - 23 -
 102. If chlorination of alkane is done at a velry high temperature,
then the relative rates of substitution of primary, secondary and
tertiary hydrogen atoms are
A) B) C) D)
103. When a compound (Z) is treated with a silver-ammonia complex, a white
precipitate
forms. Treatment of compound (Z) with ozone followed by dimethyl sulphate
and washing with water gives formic acid, 3-oxo butanoic acid and hexanoic
acid. “Z” is

a. H3C(H 2C) 4 CH C CH2 CH CH2 b. H3C(H 2C) 4 CH CH CH2 C CH2

CH3 CH3

c. H3C(H 2C) 4 CH C CH2 C CH d. HC C (CH 2)3CH C CH2 CH2 CH3

CH3 CH3

104.  CH3 2 C  CH2  2HCHO   X  , X is

H

 CH3 2 C CH 2
(a) O (b) CH 2 OH
O CH 2 OH

(c) O O (d)
O

105.
NaNH 2 1 chloro-3 bromo propane 1. Mg /dry ether
1 propyne (A) (B) +
(C)
O /H
2.
H H2 |Pd|
BaSO 4

CrO 3
(E) (D)
Identify (B) and (E)
(A) Cl (B) Br
OH O
(C) Br (D) Cl
O O

106. Correct relation between the products formed in the following reaction is
CH3
Br2/CCl4

(A) geometrical isomers (B) diastereomers

Page No - 24 -
 (C) meso compounds (D) enantiomers

107. The major product of the reaction given below is

CH3
D
Br2

h

H
CH3

CH3 CH3 CH3 CH3

Br D D Br D

A) B) C) D)
Br
H Br H H
CH3 CH3 CH3 CH3

108.

I.O 3 II. (CH 3)2S

A + B ( negative Fehlings test)

NO 2

-
- OH
A OH M B N ; Products M and N are respectively
A) B)
-
CHO - COO
COO
-
OH COO
OH and
CH 2OH and
CH 2OH

C) D) O
-
COO
OH and
-
COO
CH 2OH and
CH 2OH
NO 2 O
NO 2 OH

109. Which among the following compounds is/are not formed as the main
product in the given reaction?
+
H

Page No - 25 -
 Ph
A) B) C) D)
Ph

alcKOH .( E2 )
110. Trans-1-chloro-2 – methylcyclohexane  .Predominant product is
a) b) c) d)

111.

a) b) c) d)

112. Determine the structure of a compound having the composition C 10H10 that
has the following properties :
(i) it does not give precipitate with an ammonical solution of cuprous oxide,
(ii) when heated with dilute sulphuric acid in the presence of HgSO 4, it gives
C10H12O that reacts with hydroxylamine,
(iii) it is oxidized into isopthalic acid
C C H C C –C H 3
C C –C H 3
C C –C H 3
C H3

(a) (b) C H3 (c) CH3 (d) C H3

113. Arrange the following compounds in decreasing order of acidic character

I. Butane II. But-1-ene III. But-1-yne IV. Butan-1-ol
(A) I > II > III> IV (B) IV > II > III > I
(C) IV > III > II > I (D) I > III > II > IV
114.

Page No - 26 -
 CH2 O
C H
+ H3CO 2000C Product

H C OCH 3
CH2
O

Here, the product will be

O O
H
C OCH 3 C OCH 3

(A) (B)
C OCH 3 C OCH 3
H
O O

O
H
C OH

(C) Both (A) and (B) in equimolar raito (D) + CH3OH

C OH
H
O

115. and can be differenciated by which of the following chemical test ?

a) h (or ) then Na b) h (or ) then ammonical AgNo3

c) (or )h then Br2 / H 2O d) Cl2 / h then Br2 / H 2O

116. The correct stability order of following species is :

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

117.If the reactivity of 1°, 2° and 3° hydrogen atoms towards chlorination is 1:3:6,
the percentage of 2-chloropropane formed by monochlorination of propane is
(A) 45 % (B) 55 % (C)50 % (D) 60%
118.Addition of 1 equivalent of HCl to CH 2=C=CH2 gives

Page No - 27 -
 Cl
Cl H3 C Cl
H2C H2 C

Cl CH3 Cl Cl
(A) (B) (C) D)
119.hydrocarbon of molecular formula C10H16 incapable of showing
stereoisomerism gives C8H12O2 on ozonolysis. The hydrocarbon is

(A) (B)
CH3

CH3
(C) (D)
CH3
NOCl
H3C CH3
120.The product of the following reaction is
CH3 CH3
ON Cl
H3 C CH3 H3C CH3

(A) Cl (B) NO
CH3 CH3
H3C CH3 H3C CH3

(C) Cl (D) NO
121.Reduction of the following compound with Li/liquid NH3 gives
CH3

Li

Liquid NH3

CH3

CH3

(A) (B)

Page No - 28 -
 CH3 CH3

(C) (D)
122. Which of the following compound is not found when Br 2/H2O is added to
cyclohexene in presence of NaCl?
Br Br Br Cl

(A) OH (B) Br (C) Cl (D) Cl

123. Shown below is the final step in a synthesis of cis-jasmone, a perfume
extracted from the volatile portion of the oil from jasmine flowers. Which of the
following reagent(s) will be effective in carrying out this conversion?
CH3
CH3

CH3
O
O CH3
(A) H2/Ni
(B) H2/Pd-CaCO3 poisoned with Pb(OAc)2
(C)Na/liq.NH3
(D) Na/EtOH

124. In the following reaction, which statement is true?

CH3
H Br
X 
NaI/Acetone
A
H Br
CH3
CH3
H Br
Y 
NaI/Acetone
B
Br H
CH3
H3C CH3
Z C C  
HBr
C
H H

(A) X is optical inactive, B is cis alkene, C is a single optical active compound

(B) B is cis alkene, Y is optical active, C is a single optical active compound. A
is cis alkene too.

Page No - 29 -
 (C) A is trans alkene, B is cis alkene, C is mixture of optical active
compounds. X is optical inactive compound.
(D) Y is optcal active, B is trans alkene, C is mixture of optical active
compound, X is optical inactive compound.
125. Which of the following is having highest heat of hydrogenation?
A) B) C) D)

H PhN
126. CH3  C  C  CH3 
Ni B  X
2 3
2
Probable structure of X would be
H3C CH3
H3C CH3 C C
(A) C CH2 (B) H N
H
N
H Ph
Ph N
Ph
N
(C) CH3  CH2  CH2  CH3 (D)
H3C HC CH CH3
N N

127. CH3

Moist Ag 2O
+ CH3
N I Heat
CH3
Product, the main product is:
A) CH3 B) CH3

CH3 CH3
N N

CH3 CH3
C) D) CH2
CH3
CH3
CH3 N
N
CH3

128.

Page No - 30 -
 I.O 3 II. (CH 3)2S
A + B ( negative Fehlings test)

NO 2

-
- OH
A OH M B N ; Products M and N are respectively
1) 2)
-
CHO - COO
COO
-
OH COO
OH and
CH 2OH and
CH 2OH

3) 4) O
-
COO
OH and
-
COO
CH 2OH and
CH 2OH
NO 2 O
NO 2 OH
129.
NaNH 2 1 chloro-3 bromo propane 1. Mg /dry ether
1 propyne (A) (B) +
(C)
O /H
2.
H H2 |Pd|
BaSO 4

CrO 3
(E) (D)
Identify (B) and (E)
(A) Cl (B) Br
OH O
(C) Br (D) Cl
O O

130. H3C COOK

The main product in the Kolbe’s electrolysis of H3C COOK is

A) B) C) D)

131.

Page No - 31 -
132.

133. O
O C CH3

H Ph 
Products
H Ph 
 500 C 0

D

A) One of the products will give a racemic mixture with Br2 / CCl4

B) One of the products will give a meso product with Br2 / CCl4

C) Reaction is an example of anti-elimination

D) Entropy of reaction is negative

134. Which is incorrect product?

(A) H3C CH3

CH3  C  C  CH3 
Na / Liq.NH3
C C
H (cis) H
(B) H3C CH3
CH3  C  C  CH3 
 H2
Pd / BaSO4 C C
H (cis) H

Page No - 32 -
 (C) H CH3
CH3 CH3
H Br Br H

Br2
 
Br H H Br
H CH3
CH3 CH3
cis-But-2-ene
( ) -2, 3-Dibromobutane

(D) CH3
H CH3
H Br

Br2

H Br
H3C H
CH3
trans-But-2-ene
Meso -2, 3-dibromobutane

135. Addition of IBr to 2-methylbut-2-ene would form

(A) 2-Bromo-3-iodobutane (B) 2-Bromo-2-iodobutane
(C) 2-Bromo-3-iodo-2-methylbutane (D) 2-Iodo-3-bromo-2-methylbutane
Electrolysis
136. 1 mole HCOOH 
Na
salt  

Total moles of H2 gas produced in this entire process is

1
(A) (B) 1
2
3
(C) (D) 2
2

Page No - 33 -
ALKANE, ALKENE, ALKYNES & DIENES – KEY SHEET
Single Answers
1 A 2 C 3 B 4 C 5 D 6 D
7 C 8 A 9 C 10 B 11 C 12 D
13 B 14 B 15 D 16 B 17 B 18 C
19 B 20 A 21 D 22 B 23 B 24 C
25 B 26 A 27 D 28 C 29 A 30
31 32 33 A 34 A 35 C 36 C
37 B 38 D 39 C 40 B 41 A 42 C
43 D 44 A 45 A 46 D 47 C 48 D
49 C 50 B 51 C 52 A 53 B 54 D
55 B 56 A 57 B 58 B 59 B 60 B
61 C 62 B 63 C 64 C 65 A 66 B
67 D 68 B 69 C 70 A 71 B 72 D
73 D 74 B 75 A 76 D 77 B 78 A
79 D 80 B 81 B 82 D 83 D 84 A
85 C 86 B 87 C 88 A 89 A 90 B
91 D 92 D 93 C 94 D 95 D 96 B
97 A 98 C 99 C 100 D 101 A 102 B
103 C 104 C 105 D 106 D 107 B 108 D
109 ACD 110 A 111 D 112 D 113 C 114 B
115 C 116 C 117 C 118 B 119 C 120 C
121 D 122 D 123 B 124 C 125 D 126 B
127 D 128 4 129 D 130 C 131 D 132 B
133 A 134 A 135 C 136 C

ALKANE, ALKENE, ALKYNES & DIENES – SOLUTIONS

Single solutions
1. (A)
CH3  C  C  CH3 
Na /Liq.NH3
CH3CH  CHCH3
(Trans)
2. (C)

Page No - 34 -
 CH3 CH3 Br
I  Br 
CH3  C  CH  CH 3   CH3C CHCH3 
Br
CH3  C  CH  CH3
I CH3 I
+
3. Conceptual
4.

5. More is the substitution on isolated double bonds of diene more is the

stability and less is the  H hydrogenation .
6. Conceptual
7. Conceptual
8. A
9.

and
10. t- a stearically hindered base will give Hofmann elimination as major
product. Where as will give Saytzeffs product.

11. Conceptual

12.

In catalytic hydrogenation doubl bonds and triple bonds are reduced.

13. It has a six member ring and the five member ring found together.
14.

Page No - 35 -
15. Fact
16. It is free radical substitution at allylic position
17. Fact

18.
19. Conceptual
20. Conceptual
21. Conceptual
22. Efficient nucleophiles gives atmost speed.
23. Conceptual

Page No - 36 -
24.

25. Conceptual
26. Fact
27. d) Its pincol-pinacolone type reaction and product is formed after formation of
carbocation and its rearrangement by ring expansion.
O

Hg 2
Zn  Hg
28. CH  CH 
 CH3CHO   C2 H 6
dil H 2 SO4
HCl
29. Benzyl carbocation is more stable than alkyl carbocation.
30.
31.
32.
33. Addition of water to an alkyne.
34. Conceptual.
35. Wittig reaction
36. .Peroxide effect is not possible with HCl
37. C6 H 5CH  CH 2 
Br
 C6 H 5CHBrCHBr 
2 NaNH
3 equivalents of
 C6 H 6C  CNa 
2 CH I
 C6 H 6C  CCH 3
3

38.
Catalyst  Pt / Ni 
CH 3  CH 2  CH  CH 2  CH 2  CH 3 
H2
 CH 3  CH 2  CH  CH 2  CH 2  CH 3

In catalytic hydrogenation doubl bonds and triple bondsCHare reduced.

C CH 2 CH 3
39. sp hybridization carbons are more electro negative then sp2 carbons so alkynes
are more acdic than alkenes.

40. CH3  C  CH 

polymerisation
C6 H3 CH3 3

41. CH3  CH2  C  C  CH2 2  C  CH 

Ozonalysis
CH3  CH 2  COOH  HOOC  CH 2 2  COOH  HCOOH

42.
OH O

43.   

dil H 2 SO4 / HgSO4 Tautomerism


Page No - 37 -
 2NaOH  Cl2  NaOCl  NaCl  H 2O
NaOCl  NaO   Cl 
Cl  replaces H 

44. Br2 gives Anti addition

45. H 
1. NaNH 2
 (A)
2.CH 3CH 2 Br

3  H5C2 H
 
Na , NH liq .

(A) C=C

H C2 H5

H5C2 H
Br Br
C=C  Br2
CH 2Cl2
H C–C H
H C2 H5
H5C2 C2 H5
46. Conceptual
47. Conceptual
48. Seven dichloropentanes would be obtained as products.

1,1-dichloropentane

Cl

Only one isomer is possible

Cl

1,2- dichloropentane: It has two chirality centers

3 stereo isomers are possible
Cis isomer is a meso compound
Trans isomers is a pair of enantiomers
Cl Cl Cl
Cl H H
H H H
H Cl Cl
cis-1,2-dichloropentane trans-1,2-dichloropentane(enantiomers)

1,3-dichloropentane: It has two chirality centers

3 stereo isomers are possible
Cis isomer is a meso compound
Trans isomers is a pair of enantiomers

Page No - 38 -
 Cl Cl
Cl H H
Cl H H
H Cl Cl
H
cis-1,3-dichloropentane trans-1,3-dichloropentane(enantiomers)
49. Aromatisation
CH 3 CH 3
H 3C  CH CH 2  CH 3
 
Cr2O3 / Al2O3
8000 C

H 2C CH 2
H 3C CH 3
CH
CH 3
50.

H 2C  CH 2  COOH
KMnO4 / OH 

 
H 2C  CH 2  COOH
Adipic acid
51. (C) All the 18H  atoms are primary Hydrogens
52. Conceptual
53. Addition of HCl does not proceed via the formation of free radical, that is, no
peroxide effect.
54. (D)

Cl
ONa

Cl2 / h

Alc KOH

NBS

Br
(A) (D) (E)
(C)
aq NaOH

OH O
ONa
(F)

Na

(B)
(C)
55. Conceptual
56. (a)
Intramolecular oxymercuration – demercuration reaction
57.

Page No - 39 -
58.

O /H O/Zn
59. I CH 2  CH  CH 2  CH  CH 2 
3 2 HCHO 
O /H O/Zn
 CH  CH 
3 2  O  CH CHO
II. 3 3
 2
H aq/Hg
III. CH  CH  CH  CH  OH
2
CH CHO
3

H / O /H O
C H CH  CH  CH  C H CH  CA  CH 
3 2  PhCHO  CH CHO
6 3 2 3 6 5 3 Zn 3

IV. OH
60. Conceptual
61. Conceptual
62.

63. (C)
CH + CH
3 3
H  0
P.E. Ea Ea = 0
CH3 - CH3

Progress of reaction
64. Conceptual
65. No. of possible enantiomers

Page No - 40 -
 CH3 CH CH CH 3
CH3
h
Cl2
CH3 CH CH CH 3
CH3 CH CH 2 CH 2Cl
CH3 Cl
CH3
d and l form
Cl

CH3 C CH2 CH3 ClCH2 CH CH2 CH3

CH3 CH3
Total enantiomeric pairs = 2

66. cis -2- butene

H2O :
H H
H H
HOBr C C Optically active
C H anti addition CH3 CH3
CH3 CH3 Br ;
CH3
HO H
H H OH
C C
CH 3 CH3 Br H
Br
CH3
Threo isomer

67. Reaction occurs via formation of carbene intermediate.

CH3
CH3
CH 2N2

C H
H
68. Mg2C3 + 4H2O  C3H4 + 2Mg(OH)2
n p  rp
69. % of product =  30%
n p  rp  ns  rs  nt  rt
70. Bonds are Non-polar.

71. Less stable is the alkene, more exothermic

A  6 -hydrogen
B  1 -hydrogen
C  4 -hydrogen
D  7 -hydrogen
72. Conceptual
73. Due to bulkier base elimination occurred and alkyne is formed.

Page No - 41 -
 CH3
CH3 CH3
C C Br2/CCl 4 H Br
(i) H2/Pd/CaCO3 Br H
H H
(I)
CH3
CH3 C C CH3
(II) (i) Br2/ CCl4 CH3
CH3 CH3
C C H2/Pd H Br

Br Br H
Br
74. CH3

75. Conceptual
76.
CH 3 Ph
C C
CH 3
C C CH3
Ph CH3

CH3
 |
77. Ph  C H  CH  CH 3 (resonance stabilized)
CH3
|
Ph  C H 2  CH  CH 2Cl
*

chiral carbon
78. The percentage of Hofmann’s product increases with increasing bulkyness of
leaving group.
79. Conceptual
80. The addition will occur via cyclic iodinium ion intermediate. Hence there will
be no rearrangement. Hence no question of choice (C) or (D). Br – ion will
make nucleophilic attack from antiside on the C—atom (member of the 3-
membered cyclic intermediate) which is capable of forming more stable
carbocation. On trans- alkene antiaddition will yield meso product only when
the alkene is symmetrical. So there is no question of choice (A).
81.

Page No - 42 -
82. Branching decreases the B.P.
83. Cl F Cl
F  : B
k1
I Cl C C Cl C CF3  HB (fast)
k 1

H F carbanion
(S)

II Cl2C CF2 
k2
 Cl2 C  CF2  : F (slow)
F
Rate = k2 [Carbanion]
Also,
k1 [Carbonion][HB]
Kc  
k 1 [S] [: B ]
k c [S][B ]
 [Carbanion] = , so
[HB]
[S][B ]
Rate = k2kc
[HB]
Rate  [S] [B–] [HB]–1
84. Conceptual
85. Conceptual
decay
86. CH3  C  C  T   CH3  C  C  He3 (unstable since He3 cannot form covalent
bonds. So by taking sigma bond electron pair Helium is departing from the

alkyne as He3 . This results in the formation of CH3  C  C ).

Page No - 43 -
 
CH3  C  C

C  C  CH 3

87. Conceptual
88. Conceptual
89. Conceptual
90. to -hydroxy aldehydes.
91. H cis to oxygen will be eliminated from either side. No deuterium will be lost
as it is anti to oxygen.
92. Claisen rearrangement
93.

94. Alkene formed are CH3  C  CH 2 & CH2 = CH – CH3 and product formed
|
CH3

on ozonolysis are CH3CHO + CH3COCH3 + 2HCHO

95. Its pincol-pinacolone type reaction and product is formed after formation of
carbocation and its rearrangement by ring expansion.

96. CH 3  CH 2  C  CH 
B H
THF
(CH 3  CH 2  CH  CH )3 B
2 6


(CH 3  CH 2  CH   CH )3 B 
H 2O2 / OH
 CH 3  CH 2  OH  CH  O  H

CH 3  CH 2  CH 2  CHO

Page No - 44 -
97.
98. Anti Markowni Koff’s product is formed since carbocation
NO2

O2N CH CH3

NO2
(If formed as per Markownikoff intermediate) is least stable due to strong
electron withdrawing power
99.

100.

101. In cope reaction, syn elimination takes place.

O
D
D N
H3C H H3C D


D
102. As the temperature rises above (in thermal chlorination), the chlorine
and alkane molecules acquire so much energy that reaction occurs at
every collision irrespective of the type of bond. Under this
condition, the replacement rates will be

103. O O O O
CH3  CH 2 4 CH  C  CH 2  CH 
 2CH3  S , H2O  H  C  OH  CH 3  C  CH 2  C  OH  CH 3 CH 2 4  C  H
 3
1O
2

CH3
Page No - 45 -
104. (c)
O O OH
HO
+
H H/H
 CH3 2 C  CH 2 H H H H
H H
O O

O
CH 2

105. (D)

NaNH 2 1 chloro-3 bromo propane Mg dry ether

1 propyne (A) Cl + HgCl
O /H
(B) (C)
H
H2|Pd|
BaSO 4

CrO 3

(E) (D)
O OH
106. Conceptual
107. C-H bond is weaker than C-D bond.
108. D

109. Ph is formed as a major product

110. Conceptual
111.

112. SOL: It has six degree of unsaturation. It may be an alkyne substitued

benzene compound

Page No - 46 -
 (i) It must not be terminal alkyne
(ii) Shows it forms carbonyl compound
(iii) shows a methyl group must be meta to remaining functional group

113. General acidic character is as follows:

Alcohols > Alkynes > Alkenes > Alkanes.
114. Conceptual
115. solution : c
 
h  CH
3  CH  CH 2 
Br
H O  Decolourises
2
2
116. Conceptual
2 3
 100  50%
117. SOL: % 2-Chloropropane = 6 1 2  3
118. SOL: As the two pi bonds are perpendicular to each other, there is no
resonance assistance for the formation of allyl carbocation in the transition
state, secondary vinyl carbocation is formed.
119. SOL: All other compounds except (C) exhibit stereoisomerism.
120. SOL; NOCl breaks into NO+ and Cl- and adds Markownikov’s way.
121. Sol: Li/liq.NH3 reduces alkyne to trans-alkene.
122. Once bromonium ion is formed, any one of the nucleophiles in the system,
Br-, Cl- or H2O can attack to give (B), (C) and (A) respectively.
123. Conceptual
124. Conceptual
125. More is the substitution on isolated double bonds of diene more is the stability and
less is the  H hydrogenation .
126.
Ph N N
N
N N
H3C CH3 Ph N
CH3  C  C  CH3 
H 2 / Ni 2 B
 C C

SyN Add n  CH3
H H H3C C C
H
127. Hoffmann’s elimination.
128. 4
129. (D)

Page No - 47 -
 NaNH 2 1 chloro-3 bromo propane Mg dry ether
1 propyne (A) Cl + HgCl
O /H
(B) (C)
H
H2|Pd|
BaSO 4

CrO 3

(E) (D)
O OH
130.
The diradical formed is more stable in trans form.
131.

132. Electron withdrawing groups makes hydrogen acidic.

133. Conceptual
134. (A)
CH3  C  C  CH3 
Na /Liq.NH3
CH3CH  CHCH3
(Trans)
135. (C)
CH3 CH3 Br
I  Br 
CH3  C  CH  CH 3   CH3C CHCH3 
Br
CH3  C  CH  CH3
I CH3 I
+
1
136. HCOOH 
Na
 HCOONa  H2
2
Now, HCOONa  HCOO  Na 
1
At anode HCOO  H2  CO2  e
2
1
At cathode H 2 O  e  
 H 2  HO 
2

Page No - 48 -