193

4B
HYDROCARBONS (ALKENES)

Level - 1
1. (R)-3-bromocyclopentene (shown below) reacts with Br 2 CCl 4 to form two products, Y and
Z, Y is not optically active (does not rotate plane-polarized light). What is the structure of Y ?

¾ Br
¾2 /CCl
¾¾ 4
®Y + Z
Br
Br Br Br Br
(a) (b) (c) (d) (e)
Br Br Br Br Br Br Br Br Br

2HCl
2. A ¾¾ ¾® . Reactant (A) can be:
Cl Cl

(a) (b)
OH

(c) (d) All of these

HO

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 194
HCl
3. ; Major product of the reaction is :
CH3

(a) (b) (c) (d)

Cl
Cl Cl
Cl

O3
4. Zn

Which of the following products cannot be obtained in ozonolysis of o-xylene?

O O
CHO || ||
(a) | (b) CH 3 — C — C — H
CHO
O O O O
|| || || ||
(c) CH 3 — C — C — CH 3 (d) CH 3 — C — C — CHO

+
5. O ¾ H¾ ® Major product of the reaction is :

OH
HO
(a) (b)

(c) OH (d)

OH
CH 2 — CO 2K
6. | ¾ electrolysis
¾¾¾ ¾® ( A) (Kolbe electrolysis method)
CH 2 — CO 2K (major)

Product (A) of the reaction is :

(a) CH 3 — CH 3 (b) CH 2 == CH 2
(c) CH 3 — CH == CH 2 (d) none of these

O +
7. ¾ ¾3 ® A ¾ H¾2 ¾
Ni
® B ¾ H¾
D
® (C); Product (C) of the reaction is :
Zn Or LiAlH 4

OH O
(a) (b) (c) (d)

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 195
Br2
8. ¾ CH
¾¾ ¾® W. Product W is :
Cl2 2
OH

Br
(a) OH (b)
Br Br OH

(c) (d) OH
O Br Br
9. The reaction of propene with H 3O + will proceed with which of the following intermediates ?
Å OH OH
2
| Å |
(a) CH 3 — CH 2 — CH 2 (b) CH 3 — C H — CH 2
Å OH 2 OH
| |
(c) CH 3 — CH — CH 3 (d) CH 3 — CH — CH 3
10. Which of the following bromides is the major product of the reaction shown below, assuming
that there are no carbocation rearrangement ?

+ HBr ¾® C 13H 17 Br
(1 equivalent)

Br
Br

(a) (b) (c) Br (d) Br

11. Which of the following reactions results in the formation of a pair of diastereomers ?
H
H C CH3
(a) 3 ¾ HBr
¾¾® (b) ¾ HBr
¾¾®
CH

H3C H H 1. BH 3 , THF
(c) ¾ HBr
¾¾®
ROOR ,
(d) ¾ ¾ ¾ ¾ ¾- ¾¾®
UV 2. H 2O 2 , OH , H 2O

12. What is a likely product of the reaction shown ?

H3C H
CH3
¾ Br
¾2 /¾
CH 3OH
¾¾®

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 196
H3C H
H3C Br H3C OCH3 CH3
CH3 Br CH3 OCH3
Br
(a) OCH3 (b) CH3 (c) (d) CH3
Br Br
13. Which of the following, when undergoing addition of HBr, will form ONLY a pair of
diastereomers ?
Cl H HO H H3C CH3
(a) (b) (c) (d)

14. How many transition states and intermediates will be formed during the course of following
reaction ?
OH

H O, H +
¾ ¾2 ¾¾®
(a) 3 transition states and 3 intermediates (b) 4 transition states and 3 intermediates
(c) 3 transition states and 2 intermediates (d) 5 transition states and 4 intermediates
15. Product of which of the following reactions, is racemic mixture ?
CH3

Br
(a) ¾ H¾2 ® (b) ¾¾
¾2
®
Pt CCl 4
H3C CH3
CH3
CH3

CH3
2 H Br2
(c) ¾¾
Pd
® (d) H3C ¾ CCl
¾¾®
4

CH3

16. The product(s) of the following reaction can best be described as :

¾ HBr
¾¾®

(a) a racemic mixture (b) a single enantiomer

(c) a pair of diasteriomers (d) an achiral molecule
17. Taking into account the stability of various carbocations and, as well as the rules governing
mechanisms of carbocation rearrangements, which reaction is most likely to occur during
the given reaction ?
¾® ?
H – Br

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 197
Br

(a) ¾® Br

Br

(b) ¾® Br

(c) ¾® Br
Br

(d) None
18. Consider the following reaction in which the intermediate carbocation loses H+ to give the
final product ?
H+

Which of the following energy profiles best represents the overall reaction ?

(a) (b) (c) (d)

19. Methyl vinyl ether, H 2C == CH — OCH 3 , reacts with Br 2 CH 3OH. If methanol is reacting as
water would, and if this reaction follows a typical mechanism of electrophilic addition, what
would be the expected product ?
Br Br OCH3 OCH3 Br O
OCH
Br
(a) (b) (c) (d)
H3CO OCH3 OCH3 OCH3
20. 2, 4-hexadiyne (C 6 H 6 ) is allowed to react with Li in NH 3 (liq). The product obtained is
treated with 1 equivalent of Cl 2 in CCl 4 . Which of the following constitutional isomers are
possible products ?
Cl Cl Cl Cl Cl Cl

Cl Cl Cl Cl
(I) (II) (III) (IV) (V)

(a) I and II (b) II and III

(c) I and V (d) I and III
21. Which of the following is the best stereochemical representation when reaction between
1-methylcyclohexene and NBS react in aqueous dimethyl sulfoxide ?
OH OH
Me Me
(a) (b) (c) (d) None of these
Br Br
Br

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 198
22. Which of the following is among the major products of the reaction of
(E)-3-methyl-2-pentene with BH 3 in THF followed by the addition of H 2O 2 HO - ?
OH OH H Me
Et H Me H Me OH H H
(a) (b) (c) (d)
H Me H Me H Me Et OH
Me Et Et Me
23. Compare rate of dehydration of (i), (ii) and (iii) by conc. H 2SO 4 .
OH
OH
(i) (ii) (iii)
OH
(a) (i) > (iii) > (ii) (b) (i) > (ii) > (iii)
(c) (ii) > (i) > (iii) (d) (ii) > (iii) > (i)
24. How many products will be formed in this reaction ?

1. OsO 4
¾ 2.
¾NaHSO
¾¾¾®
3

(a) 10 (b) 2
(c) 3 (d) 4
H H
Br
25. C == C == C 2
¾CCl
¾
¾ ® (A). Product (A) of the reaction is:
CH3 C(CH3)2CH2OH 4

Br Br
CH3 H CH3
(a) CH3 (b)
CH3 O CH3 O CH3
Br
CH3 CH3
(c) (d)
H CH3 O Br
O
CH 3
|
HF
26. CH 3 — CH + H 2C == CH 2 ¾ 2¾¾
- 5°C
® ( A); (A) is:
|
CH 3

(a) (b)

(c) (d) CH 3 — CH — CH 2 — CH == CH 2
|
H CH 3

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 199
27. Predict the product ( A) of the following reaction

H+
A
D

(a) (b) (c) (d)

OH
H+
28. (A) Major-product ( A) is:
D (Major)

(a) (b) (c) (d)

29. Di-imide (N 2H 4 ) is used to reduce double bond of:

(a) — C == O (b) — C ºº N (c) —NO 2 (d) — CH == CH —
|
Na Cr O
30. ¾¾®( A) ¾ NaHCO
¾ HCl ¾H¾¾
O
3
® ( B ) ¾ ¾2¾2 ¾
7
® (C )
2 C 5 H 8O

End product of the reaction is :

O OH O
O
(a) (b) (c) (d)

HBr
31. A
CCl4 (Major)
Product ( A) is :
Br
Br
Br

(a) (b) (c) (d)

Br
)
xcess
H 2(e
Pt
32. A KMn
O4 CO2H CO2H
+
CO2H CO2H

Compound (A) is :

(a) (b) (c) (d)

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 200
OH

OsO4
33. X + Y
12 : 1

Product (X) will be :

OH OH OH

OH OH
(a) (b) (c) O (d) O
OH OH
Br2 2NaNH2 H2
34. CH == CH A B C
CCl4 Pd/CaCO3

Product (C) is :
Ph H Ph Ph Ph
(a) C == C (b) C == C (c) C == CH2 (d) Ph — C ºº C — Ph
H Ph H H Ph

MMPP(one-equivalent)
X
35. Ethanol 74%

MMPP ¾® Magnesium mono peroxy phthalate.

Product (X) is :

(a) O (b) O

OH

(c) HO (d)
HO
OMe OH

36. MCPBA P ; Product (P) is :

75%

O
OMe
OMe
O

(a) (b)

O O
O

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 201
OMe

(c) (d) None of these

O
O O

CH3 CH3
O O
KOH
37. N Os N A ; Product (A) is :
Mannitol/Water
O O
Cyclic osmate ester complexed
with pyridine

(a) HO CH3 (b) CH3 CH3

CH3 OH OH OH

(c) (d) CH3

O CH3
CH3

hn
38. + CBrCl 3 ¾ ¾ ® ( A) (no ring substitution)

Product (A) is :
(a) Ph — CH 2 — Cl (b) Ph — CH 2 — Br
(c) Ph — CH 2 — CCl 3 (d) Ph — CH 2 — CBrCl 2

MCPBA
39. (A) ; MCPBA ¾® metachloroperbenzoic acid

Product (A) of the above reaction is :

(a) O (b) O

HO
(c) OH (d)

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 202
40. The major product of the following reaction sequence is :
1. B2 H 6
¾ 2.
¾H¾O¾ ¾¾®
, HO
?
2 2

OH OH O H HO
(a) (b) (c) (d)

41. Which one of the following compounds gives acetone (CH 3 ) 2 C == O as one of the product of
its ozonolysis ?

(a) (b) (c) (d)

42. Addition of HCl to 3, 3-dimethyl-1-butene yields two products, one of which has a rearranged
carbon skeleton. Among the following carbocations, select the possible intermediates in that
reaction ?
+ + + +
(CH 3 ) 3 CCHCH 2Cl (CH 3 ) 3 C C HCH 3 (CH 3 ) 2 C C(CH 3 ) 2 (CH 3 ) 2 C CH(CH 3 ) 2
|
Cl
1 2 3 4
(a) 1, 2 (b) 1, 3 (c) 1, 4 (d) 2, 3
(e) 2, 4
43. Conversion of cyclohexene to cyclohexanol can be conveniently achieved by :
(a) NaOH + H 2O (b) Br 2 — H 2O
(c) hydroboration, oxidation (d) hydroboration hydrolysis
44. Trans-cyclohexane-1,2-diol can be obtained by the reaction of cyclohexene with :
(a) KMnO 4 (b) OsO 4
(c) peroxy formic acid /H 3O + (d) SeO 2
45. Bromination of (E)-2-butenedioic acid gives
(a) (2R, 3S)-2, 3-dibromosuccinic acid
(b) (2R, 3R)-2, 3-dibromosuccinic acid
(c) a mixture of (2R, 3R) and (2S, 3S)-2, 3-dibromosuccinic acid
(d) (2S, 3S)-2, 3-dibromosuccinic acid
46. The major product formed during the reaction of 1-methyl cyclopentene with CH 3CO 3H is
CH3 CH3 CH3 CH3
(a) (b) OH (c) O (d)
OH OH
CH — CO 2H
electrolysis
47. || ¾ NaOH
¾¾® ( A) ¾¾¾¾¾® ( B ); Product (B) of the reaction is :
CH — CO 2H (two mole)
(a) CH 3 — CH 3 (b) H 2C == CH 2
(c) H — C ºº C — H (d) CH 2 == CH — CH == CH 2

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