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SHEET – 5 – ALKENE
(Properties of Alkenes)
1. Which reagent is best to perform the following transformation?

(A) HBr, NaOH (B) HBr, R  O  O  R, hv; Me3COK

(B) BH 3 , THF, NaOH  H 2 O 2 (D) Br2 , NaOH

H3C Ph
Cl2 ,CCl 4
2. C=C  

H H

Ph Ph
H Cl
(A) H Cl (B)
Cl H H Cl
CH3 CH3

Ph
H Cl
(C) Ph  C  C  CH 3 (D)
H CCl3
CH3

3. Give the major product of following reaction

Br2 /CCl4
  Major product:

OH
Br
Br

(A) (B)

Br
OH Br
Br

O
(C) (D)
O

Hg(OAc)2 ,H 2 O
4. 
NaBD ,  OH
Major product:
4

(A) OH (B)
OH

(C) D (D)
OD
OH D

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Ph
Hg(OAc)2 ,CH3 OH
5. C = CH - CH3 
NaBD ,  OH
 Major product:
4

CH3

Ph CH2 - CH3 OCH3

(A) C (B) Ph CH - CH3
CH3 OH C
CH3 H
Ph CHD - CH 3
(C) C (D) None of these
CH3 OCH3

Cl 2 2NaNH2 H2 ,Pd-CaCO 3
6. Ph  CH  CH  Ph 
CCl 4
 X   Y  Z
Identify product (Z) of the reaction.

Ph H Ph Ph
(A) C=C (B) C=C
H Ph H H
Ph

(C) C = CH2 (D) Ph  C  C  Ph

Ph

7. Point out (A) in the given reaction sequence:

O3 / H2 O 
(A)   (B)   HOOC — CH2 — COOH

(A) (B)

(C) (D)

H3C CH3
Br2  H2 O
8. C=C   Product:
H H
CH3 CH3
H Br H Br
(A) (B)
H OH HO H
CH3 CH3
CH3
CH3
H3C OH
(C) H3C OH (D)
H Br
Br H
H
H

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10. Which of the following reactions are correct?

Br2 /CCl4 CH 3 CO3 H

(A)   (B) 
H /H O

2

Br Br
Me Me
HBr
(C) 
 (D) H /H2 O
Me 

HO
Br Me Me Me
Passage – 1
Addition of X2 on alkene is electrophilic addition reaction. Reaction proceed through the formation of 3-
membered cyclic halonium ion. Nucleophile X  attacks from backside of cyclic halonium ion hence total
reaction is anti addition reaction. If this reaction proceed in polar solvent then solvent itself acts as
nucleophile.
X

C=C + X2 C=C

X
Mechanism:

11. Which of the following statement is incorrect?

(A) Symmetrical trans alkene gives 2 products on reaction with Br2 /CCl 4
(B) Symmetrical cis alkene gives 2 products on reaction with Br2 /CCl 4
(C) Trans alkenes give erythro product
(D) Cis alkenes give threo product

Cl2 (1 Mole)
12.  CCl4
 

(A) (B)

Cl

Cl
Cl

(C) (D)

Cl

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Ph CH3
Cl2 ,CH 3 OH
13. C=C   Major product:
H H

Ph Ph Ph Ph
H Cl
(A) H Cl (B) H OCH3 (C) H Cl (D) H OCH3
CH3 Cl H3CO H Cl H
H CH3 CH3 CH3
Passage – 2
Addition of HX on alkene proceed through the formation of carbocation. This reaction is also known as
Markownikoff reaction. According to Markkownikoff’s rule addition of electrophile occurs on that carbon of
alkene which have more of ‘H’ atom.
X
HX
Ph  CH  CH 2  Ph - CH - CH3 + Ph - CH - CH - X
2 2
Major Minor
Mechanism:

14. Which of the following alkenes can produce diastereomers?

(A) CH 3  CH  CH  CH 3 (B) CH = CH - CH3

H CH3
CH3

(C) (D) CH 3  CH  CH 2

15. Which of the following alkenes will give Markownikoff reaction?

HCl HCl
(A) F3 C  CH  CH 2   (B) H3 N  CH  CH 2  

CH3
HBr HBr
(C) O2 N  CH  CH 2   (D) C = CH2  
CH3

16. Arrange the following alkenes in decreasing order of reaction with HBr:
CH3 CH3 CH3 CH3
C = CH2 C = CH2 C = CH2 C = CH2
CH3 CH3 O H3C N CH3 - O - CH2

(P) (Q) (R) (S)

(A) P  Q  R  S (B) R  Q  P  S (C) S  R  Q  P (D) Q  R  P  S

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Passage – 3
P(C 5 H 9 Br)
NaNH2

Decolourise Br2 water

O3
Q and cold KMnO4 Q 
Me2 S
T
(Not react with Na)

Lindlar catalyst Na/NH 3 (l)

R S
(C 5 H10 ) (C5 H10 )

17. Which of the following is compound P ?

Br Br

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

Br Br
18. R and S are:
(A) Position Isomers (B) Enantiomers
(C) Geometrical (D) Functional Group Isomers
19. Identify structure of compound T :

O O
(A) CH3 - C - OH (B)

O
(C) CH3 - CH2 - C - OH (D) CH3 - C - H
O O
Passage – 4
Hydroboration oxidation reaction is a process of addition of H2 O according to antimarkownikoff’s rule.
BH3 .THF
CH 3 CH  CH 2    CH 3  CH 2  CH 2  OH
H 2 O2 ,O H

Reaction is regioselective. Regioselectivity of reaction is increased by using hindered boranes.

THF (Tetrahydrofuran) is used to control reactivity of borane.

CH3 CH CH2 CH3 CH CH2

+ CH3CH2CH2BH2
H BH2 H BH2
2CH3 CH CH2
(CH3CH2CH2)3 B
or
R CH3CH2CH2
H - O - O - H + OH O - O - H + H2O

OR
2 OH RO - B - OR
O-H

3 R - OH + BO-3 3
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20.
BD3 . THF
 18  Major product.
H 2 O2 , OH

CH3 CH3 CH3 CH3

18
(A) D (B) D (C) OH (D) OH
OH OH D OH
H H H H

HOOC H
BD3 ,THF
21. C=C   
D2 O2 ,O D

H COOH

COOH COOH
H D H OD
(A) (B)
H OD H D
COOH COOH

COOH COOH
H D
(C) D H (D)
H OD H OH
COOH COOH

22. The addition of Br2 to cis2butene produces

(a) (+)2, 3dibromobutane only (b) ()2, 3dibromobutane only
(c) (+/–) 2, 3dibromobutane (d) meso2, 3dibromobutane

Ozonolysis of will give

23.

O
(A) 2 (B) O

O
O

(C) (D)
2

24. CH3
|
H–C
|| alkaline KMnO 4
    A
H–C
|
CH3
Which is true about this reaction?
(A) A is meso 2, 3-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 1, 2-butan-di-ol formed by anti addition
(D) A is a racemic mixture of 1, 2-butan-di-ol formed by syn addition
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27. Match the following
Column I Column II

Ph
HBr
(A) C = CH2   P. Free radical
CH3 CH2

CH3
HCl
(B) H D   Q. Enantiomer

CD

CH2
CH3
NBS
(C)   R. Diastereomer

Ph
HBr
(D) C = CH2 
H2 O 2 , hv
 S. Carbocation
H3C

28. Match the following

Column I Column II

HBr
(A) Markownikoff product P. CH 3  CH  CH 2 
H 2 O2 , hv


H3C CH3
(B) Antimarkownikoff product Q. C=C CHCl 3  KOH
 
H H

HCl
(C) Peroxide effect R. CH = CH2  

HBr
(D) Mixture of stereoisomers S. CF3  CH  CH 2  

29. Which compound will yield 5-keto-2-methyl hexanal upon treatment with O3 ?
CH3 CH3
CH 3
CH 3

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

CH3 CH3

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30. An organic compound on reaction with O3 followed by Zn and H 2 O gives

O O
CH3 - C - CH2 - CH2 - C - CH3. The structures are:

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

31. An alkene of molecular formula C4H8, having zero dipole moment, on treatment with cold
aqueous KMnO4 gives :
(a) optically inactive non resolvable solution (b) optically inactive resolvable solution.
(c) optically active non resolvable solution. (d) optically active resolvable solution.

CH3C=CHCH3
32. The treatment of with hot acidic KMnO4 produces
CH3
(a) CH3COCH3 + CH2O (b) CH3COCH3 + CH3COOH
(c) CH3CHO + CO2 (d) CH3COCH3 only
33. The compound most likely to decolourize a solution of potassium permanganate is

(a) CH3CH3 (b)

CH3
CH3CCH3
(c) CH3CH=CHCH2CH3 (d)
CH3
34. The olefin, which on ozonolysis gives CH3CH2CHO and CH3CHO?
(a) But1ene (b) But2ene
(c) Pent1ene (d) Pent2ene
35. The ozonolysis of an olefin gives only propanone. The olefin is
(A) propene (B) but–1–ene
(C) but–2–ene (D) 2, 3–dimethylbut–2–ene
36. The treatment of CH3C = CH2
|
CH3
with boiling KMnO4 produces
(A) CH3COCH3 + CH2O (B) CH3CHO + CH3CHO
(C) CH3COCH3 + CO2 (D) CH3COCH3 + HCOOH
37. Select the best starting material for the following reaction:

O 3 ,Zn-H 2 O
?  

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

38. Cyclohexene on reaction with OsO4 followed by reaction with NaHSO3 gives
(a) cisdiol (b) transdiol
(c) epoxide (d) alcohol

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ANSWER KEY
SHEET – 5 – ALKENE
(Properties of Alkenes)
1. B
2. A
3. C
4. B
5. C
6. B
7. C
8. B
9. BC
10. ABC
11. A
12. B
13. D
14. C
15. D
16. B
17. A
18. C
19. B
20. B
21. C
22. C
23. B
24. A
25. A
26. C
27. A  Q, S; B  R, S; C  P, Q; D  P, Q
28. A  R, S; B  P, S; C  P; D  Q, R
29. B
30. A, B, C
31. B
32. B
33. C
34. D
35. D
36. C

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