The reagent for the following conversions is : (for questions 1 to 5) (only one answer correct)

1. 
(A) CH3OH / H+ (B) CH3CH2OH / H+ (C) H2O / H+ (D) HOCl / H+

2. CH3CH = CHCH3  CH3 CHCH2CH3

|
OCH2CH3
(A) CH3OH / H+ (B) CH3CH2OH / H+ (C) H2O / H+ (D) HOCl

3. 

(A) CH3OH / H+ (B) CH3CH2OH / H+ (C) H2O / H+ (D) HOCl / H+

4. 

(A) LiAlH4 (B) H2 / Ni (C) NaBH4 (D) H2 / Pd / CaCO3

5.

Which reagent you will use for the above conversion ?

(A) Pd / CaCO3, H2 (B) Na / NH3
(C) Li / C6H5NH2, NH4Cl (D) None of these

The end product of following reactions is (Q. 6 to Q. 17)

Ph – CH2 – CH = CH2  2 

dil. H SO
6. 4


H H H
| | |
(A) Ph  C  CH2  CH3 (B) Ph  C  C  CH3
| | |
OH H OH

H H
| |
(C) Ph  C  C  CH3 (D) Ph – CH2 – OH
| |
OH H

 2 
 
dil. H SO
4
7.

(A) (B) (C) (D)

21
  2 
 
dil. H SO
4
8.

(A) (B) (C) (D)

 2 
 
9. dil. H SO
4

(A) (B)

(C) (D)

 2 
 
10. dil. H SO
4

(A) only (B) only

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

 2 
 
11. dil. H SO
4

(A) (B)

(C) (D)

22
12.

OH H OH
| | |
(A) CH3  C  CH2  CH3 (B) CH3  C  C  CH3
| | |
CH3 CH3H

H H H
| | |
(C) CH3  C  CH2  CH2  OH (D) HOCH2  C  C  CH3
| | |
CH3 CH3H


13. HBr

(A) (B) (C) (D)

  2 
 
14. HBr / R O
2

(A) (B) (C) (D)


15. HCl

(A) (B) (C) (D)

16.

(A) (B)

(C) (D)

23
17.

(A) (B)

(C) (D)

18. Arrange in decreasing order of reactivity with HCl

(A) I < III < II (B) III > II > I

(C) III > I > II (D) none of the above

19. F3C – CH = CH2 + HCl 

H
|
(A) F3 C  C  CH3 (B) F3C – CH2 – CH3 (C) F3 C  CH  CH2 (D) F3CCH2CH2Cl
| | |
Cl Cl Cl

20. CH3O – CH = CH2 + HCl (dry) 

H H
| |
(A) CH  C  CH (B) CH3  O  C  CH3
3 3
| |
Cl H

H Cl
| |
(C) CH3  O  C  CH3 (D) CH3  O  C  CH3
| |
Cl Cl

21. Give the major product obtained from the reaction of the following with HBr.

(A) (B) (C) (D)

24
22. The product of following reaction can be :


HBr

(A) (B) (C) (D)

23. CH3  CH  CH  CH2

|
Br
(A)
(1, 2  addition )
Both the major product Aand B are
(A) Kinetically controlled product
(B) Thermodynamically controlled product
(C) Both
(D) A is kinetically, B is thermodynamically controlled

 A   B
     
(1) HBr ( 2moles ) (2) Zn
24.
R 2O 2 Ether

(A) A is (B) A is (C) B is (D) B is


25. HBr

(A) (B) (C) (D)

CH3  C  CH
2 

26. Bayer's reagent

|
CH3

OH OH OH
| | |
(A) CH3  C  CH2 (B) CH3  C  CH3 (C) CH3OH (D) none of the above
| |
CH3 CH3

25
27.

(A) (B)

(C) (D)

     

Bayer 's reagent
28. dil (cold KMnO 4 )

(A) (B) (C) (D)

29.

(A) (B) (C) (D)

30.

OH H OH
| | |
(A) CH3  C  CH2  CH3 (B) CH3  C  C  CH3
| | |
CH3 CH3H

H H H
| | |
(C) CH3  C  CH2  CH2  OH (D) HOCH2  C  C  CH3
| | |
CH3 CH3H

31.

(A) (B) (C) (D)

26
  
32. 2 2 CH N

(A) (B) (C) (D)

 BH
 
(1)
3
33.
( 2 ) H2O 2 , OH ¯

(A) (B) (C) (D)

  
3BH , THF
H2O 2 , OH ¯
34.

(A) (B)

(C) (D)

35.

OH H OH
| | |
(A) CH3  C  CH2  CH3 (B) CH3  C  C  CH3
| | |
CH3 CH3H

H H H
| | |
(C) CH3  C  CH2  CH2  OH (D) HOCH2  C  C  CH3
| | |
CH3 CH3H

(1) Hg(OAc ) / THF  H O

36.     
2
  2
(1) NaBH4 / OH¯

(A) (B) (C) (D) all of these

27
   2 32 2
(1) Hg (O CCH ) ,H O
37.
( 2 ) NaBH4  NaOH

(A’) (B)

(C) (D)

 
CH N
2 2
38. 

CH3 H
| |
HC  C  CH3
(A) (B) | |
CH3 H

(C) (D)

39.

(A) (B)

(C) (D)

40.

(A) (B)

(C) (D)

28
 (CH3)3CCl   
 A  3  B
alc. KOH 3 CF CO H
41. 
The product ‘B’ is

(A) CH2 = CH – CH2OH (B)

(C) CH3COCH2CH3 (D) (CH3)2CHCH2OH

42.

(A) (B) (C) (D)

43.

(A) (B) (C) (D)

44. Allyl alcohol + Br2 / CCl4 

CH2  CH  CH2
(A) (B) CH3  C(Br ) 2  CH2
| | | |
Br Br OH OH

(Br )2  CH  CH2  CH2 CH2  CH  CH2

(C) (D) | | |
|
OH Br Br Br

45. Which alkene you will choose to prepare (2R, 3S)-2, 3-Dibromobutane, by the reaction with
Br2 / CCl4

(A) (B) (C) (D)

Ph – CH = CH2    
  (A)      
 (B)
BrCl / CCl aq. NaOH (1eq.)
46. 4

H H
| |
(A) A is Ph  C  CH2  Br (B) B is Ph  C  CH2  Br
| |
Cl OH

H H
| |
(C) A is Ph  C  CH2  Br (D) B is Ph  C  CH2  Br
| |
OH Cl

29
47. + Br2 

(A) (B) (C) (D)

  (stereoisom er )
2Br
48.
CCl 4 ( )

(A) (B) (C) (D)

49. CH3 – CH = CH2

(A) CH3 – CH2 – CH2 – Br (B) CH3  CH  CH2  Br

|
O  CH2  C  C  CH3

(D) CH3  CH  CH3 (D) CH3  CH  CH2  O  CH2  C  C  CH3

| |
Br Br

 
 
CHBr
3
50.
t BuO ¯ K


(A) (B) (C) (D)

trans-2-pentene    
2 Cl / CCl
4
51.

(A) (B) (C) (D)

30
 cis-2-Butene2 
Br / H O
2
52.

(A) (B) (C) (D)

53.
(A) CH2 = CH – O – CH = CH2 (B) RO – CH2 – CH2 – – CH2 – CH2 – OR
(C) ClCH2CH2 – OH (D) CH3 – CH2 – Cl

54. Give the structure of the alcohol that is formed from the acid-catalysed hydration of the following
alkene.

(A) (B) (C) (D)

55. The product of the following reaction would be :

(A) (B)

(C) (D)

56. C2H3O2Cl + H2O 

CH2  CHO Cl  CH  COOH CH2  COOH

(A) | (B) (C) CH3  CH  OH (D) |
|
OH |
OH OH
Cl

MnO ¯ / H O, OH ¯
  4   
 A  4 2 
(1) OsO / Pyridine
57. A is
( 2) NaHCO3 , H2O Cold

(A) (B) (C) (D) none of these

31
58. Products

Which one is true below ?

(A) Both products reduce Fehling’s solution (B) Both products do not reduce Tollen’s reagent
(C) One of them will reduce Tollen’s reagent (D) Both are optically inactive

CH2  CH  COOH
  
59. Zn dust
| |
Br Br

CH2  CH  CHO CH2  CH  COOH

(A) | | (B) CH2 = CH – COOH (C) CH  CH  COOH (D)
| |
Br Br Br
Br

60. Rate of hydrogenation of the following alkenes is

(A) II > IV > III > I (B) IV > II > III > I (C) IV > II > I > III (D) IV > I > II > III

61. Reactivity order towards electrophilic addition of the following alkenes is

(A) IV < III < I > II (B) IV > III > I > II (C) IV > I > III > II (D) IV > I > II > III

62. Rate of hydration of the following alkenes is

(A) I > II > III > IV (B) I < II < III < IV (C) I > IV > III > II (D) I > IV > II > III

63. Rate of hydrohalogenation of the following alkenes is

(A) I > III > II > IV (B) II > I > III > IV
(C) II > I > IV > III (D) I > II > IV > III

32
64. Rate of addition of Cl2 / H2O of the following alkenes is

(A) IV > III > I > II (B) IV > III > II > I (C) I > II > III > IV (D) I > II > IV > III

65. Stability of carbocation is

CH3 CH3
| |
CH3 CH2 C CH3 CH3 CH2H C CH3 CH3 CHCH2 C H2
 

I II III

(A) I < II < III (B) II < I < III (C) II < I < III (D) I > II > III

66. Stability of carbocation is

  
CH3 CHCH2 C H2 CH3 CH2CH2 C H2 CH3 CH2CH C H2
|
|
Cl II Cl
I
III
(A) II > III > I (B) I > III > II (C) II > I > III (D) I > II > III

67. Match the relative reactivity of the following alkenes towards bromine in methanol solution.

Compound Re lative Ra te

I . (CH3)2C = CH2 a. 6.0 × 103

II . CH2 = CH2 b. 1.0

III . (CH3)2C = CHCH3 c. 3.0 × 101

I II III
(A) a b c
(B) b a c
(C) c b a
(D) b c a

68.

(A) (B) (C) (D)

69. The product ‘X’ can be

I2   
  X
Na CO
2 3

(A) (B) (C) (D)

33
70. An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic
reduction to give deccalin. When treated with warm, connected potassium permangate, this com-
pound give cis–cyclohexane–1,2–dicaboxylic acid and oxalic acid. Propose a structure for the
unknown.

(A) (B) (C) (D)

71. Select the correct statement/s

(A) CH3–CH = CH–CH3 adds HBr in the presence and in the absence of peroxide to give the same
product.
(B) CH3 – C  CH2 when treated with H2O/ H2SO4 gives C4H10O which can be resolved into optical
|
CH3
isomers.
CH3
|
(C) C 2H5 – C – CH  CH2 is an optically active hydrocarbon which on catalytic hydrogen atom
|
H
CH3
|
gives C 2H5 – C – C 2H5
|
H
(D) None of the above

Answers
EXERCISE - 1
1. A 2. B 3. D 4. B
5. A 6. C 7. A 8. C
9. A 10. D 11. C 12. A
13. B 14. A 15. C 16. A
17. B 18. B 19. D 20. C
21. B 22. D 23. D 24. A
25. D 26. A 27. D 28. A
29. C 30. C 31. A 32. D
33. B 34. C 35. B 36. A
37. A 38. C 39. B 40. A
41. B 42. C 43. C 44. A
45. D 46. B 47. B 48. C
49. B 50. A 51. B 52. B
53. A 54. A 55. C 56. D
57. A 58. C 59. B 60. A
61. B 62. C 63. D 64. B
65. D 66. C 67. C 68. A
69. A 70. D 71. C

34
Assertion Reason type Question
(A) If both assertion and Reason is correct explanation of A
(B) If both assertion and Reason are correct but Reason is not correct explanation of A
(C) If assertion is correct, reason is wrong
(D) If assertion is wrong, reason is correct

1. Assertion : is more easily hydrated than

Reason : is more stable carbocation than

2. Assertion : Addition of HCI to 1-isopropenyl–1–methylcyclopentane yields 1–chloro–1,2,

2–trimethylcyclohexane.
Reason : Mechanism of reaction is

H


3. Assertion :

and

on hydration give same alcohol.

Reason : The intermediate carbocation for both the alkenes is same.

4. Assertion : The addition of CBrCl3 in the presence of peroxides takes place faster to 2-ethyl-1-
hexene than to 1-octene.
Reason : Due to formation of 1° free radical in case of 2 ethyl-1-hexene

5. Assertion : The hydroboration oxidation of

gives

Reason : The syn addition of BH3 across the double bond of norbornane takes place mostly from
the more accesible outside face of the double bond.

6. Assertion : The addition of chlorine to cyclohexene gives a racemic mixture of trans-1, 2-

dichlorocyclohexane.
Reason : The trans-1, 2-dichlorocyclohexane is less sterically crowded than cis-1, 2-
dichlorocyclohexane hence easily formed.

35
7. Assertion : A peroxyacid epoxidizes an alkene by a concerted electrophillic reaction where sev-
eral bonds are broken are formed at the same time.
Reason : The reaction between an alkene and the peroxy acid is a one step reaction which gives
the epoxide and the acid directly without any intermediates.

8. Assertion : In the ozonolysis of alkenes the ozonide is formed before molozonide.

Reason : The molozonide has two peroxy linkages so it is quite unstable.

9. Assertion : cis and trans isomers of an alkene cannot be distinguished by ozonolysis.

Reason : The attack of ozone on the double bond is not stereospecific.

10. Assertion : BrCH2CH2CH2CH = CH2 on treatment with followed by Na / ether gives

Reason : the ether formed is due to neighbouring group participation.

Answers
EXERCISE - 2
1. D 2. A 3. A 4. C
5. A 6. C 7. A 8. D
9. C 10. C

36
One or more than one answer can be correct.

1.  (A) 
Br2
 (B)
KCN
CH3 OH

(A) A is (B) B is

(C) A is (D) B is

2.

(A) A is (B) B is (C) C is (D) A is

3. Write the products of the following reaction :

(A) A = (B) A is (C) B is (D) B is

trans-2-Butene2 
D / Ni
4.

(A) (B) (C) (D)

5. Which of the following carbocations would you expect to rearrange ?

CH3
|
(A) (B) (C) (D) CH3 CH C HCH3


37
6. Select the correct statements
(A) Additon of chlorine water to Cis-2-Butene gives the racemic threo chlorohydrin
(B) Addition of chlorine water to Cis–2–Butene gives the racemic erythreo chlorohydrin
(C) Addition of chlorine water to trans–2–Butene gives the racemic erythreo chlorohydrin
(D) Addition of chlorine water to trans–2–Butene gives the racemic threo chlorohydrin

7. Alkenes (A) & (B) yield the same alcohol (C) on hydration. On vigorous oxidation with KMnO4 (A)
gives a carbonyl compound (D) and an acid (E), each containing four carbon atoms. On the other
hand (B) gives an acid (F) and a carbonyl compound (G). In (G) no two identical groups are
attached to the same carbon [Link] the correct structure.

(A) A is (B) C is

(C) D is (D) F is CH3 CH2 CH2 COOH

Answers
EXERCISE - 3
1. C, D 2. A, B, C 3. A, D 4. B, C

5. A, B, D 6. A, C 7. A, B, C, D

38