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Mechanism of

Organic
Reactions
For world of competitions

By

AJNISH GUPTA & BHARTI GUPTA


Professor of Organic Chemistry

(i)

Copyright 2015 by Ajnish Gupta


All rights reserved.
No part of this publication may be reproduced, stored
in a database or retrieval system, or transmitted in any
form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior
written Permission of the writter.

First Indian Reprint, 2015


This edition is ma nufa ctured in India n a nd is
authorized for sale only in India, Bangladesh, Pakistan,
Nepal, Sri Lanka & Maldeves.
Printed & Distributed by:
Udaan Classes Pvt. Ltd.
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&
Madhur Satyapushpa
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9122057123
Price: Rs. 499/-

(ii)

Preface
The guiding principle in writing this book was to create
a textbook for students- a textbook that presents the
ma terial in a way tha t they le arn to solve all the
questions along with the strategy to approach the
problems.
In this book we mixed all our teaching experience of 11
yea rs a long with theora tica l a nd experimenta l
knowledge to generate a hand book for all students to
reason their way to a solution rather than memorize a
multitude of facts, hoping they dont run out of memory.
This book covers mainly 6 units along with 10 test
papers to judge your knowledge which help you to solve
chemical reactions of organic chemistry and remove the
fever of mechanism of organic reactions.
Organic chemistry is very easy and conceptual subject
and need proper understa nding of the basics a nd
stretegy to solve the questions in corret manner.
This book a lso covers a ll the questions of AIEEE,
IIT-Mains, IIT-Advanced, AIPMT & other medical
exams from 2000 to 2015.
In this book balance has to be achieved between the
number of questions and the quality of the questions,
especially because it is relatively easy to frame a very
large number of multiple-choice questions and theory
of the subject.
We would like to thank the editors and production staff
for their efforts in bringing out the book. Suggestions
from readers for the improvement of the book are welcome.
Ajnish Kumar Gupta & Bharti Gupta
Ajnish@OrganicChemistry.co.in
9122057123

(iii)

Acknowledgement
We are tha nkful to all the teachers who taught us
during the concept building session of our life specially
Dr. Nizamuddin sir, senior Chandra Vijay Rao and Dr.
Vijay Pratima Mittal madam.
We have written this book to remove the fever of
organic chemistry from mind of students.
We particularly want to thank many wonderful and
talented students whom we have taught over the years
who in turn taught us how to be a good teacher and
how we can help others.
We want to make this book as user friendly as possible,
and we will appreciate any comments that will help us
to achieve this goal in future editions.
Finally, this edition has been presented before you with
efforts to make it error free. Any that remain are our
responsibility; if you find any, please let us know so they
can be corrected in future printing.
Ajnish Gupta & Bharti Gupta
Professors of Organic Chemistry
Ajnish@OrganicChemistry.co.in
09122057123

(iv)

Table of Contents
Page No.
01

Unit 1 : Alkene and Alkynes


Exercise 01 : Subjective approach

02

Answer

68

: Subjective approach

Exercise 02 : Objective approach

08

Single correct questions (SCQ)

08

Multiple correct questions (MCQ)

41

Assertion/reason type questions (A/R) 50

Answer

Match the column type ques. (MTC)

52

Comprehension type questions

54

Integer type questions

59

: Objective approach

81

Exercise 03 : World of competition

60

Answer

83

: World of competition

Unit 2 : Oxidation, Reduction & Alkane

84

Exercise 01 : Subjective approach

85

Answer

143

: Subjective approach

Exercise 02 : Objective approach

92

Single correct questions (SCQ)

92

Multiple correct questions (MCQ)

112

Assertion/reason type questions (A/R) 118

Answer

Match the column type ques. (MTC)

120

Comprehension type questions

123

Integer type questions

126

: Objective approach

(v)

154

Exercise 03 : World of competition

129

Answer

156

: World of competition

157

Unit 3 : Aromatic compounds


Exercise 01 : Subjective approach

158

Answer

242

: Subjective approach

Exercise 02 : Objective approach

172

Single correct questions (SCQ)

172

Multiple correct questions (MCQ)

194

Assertion/reason type questions (A/R) 199

Answer

Match the column type ques. (MTC)

202

Comprehension type questions

204

Integer type questions

207

: Objective approach

268

Exercise 03 : World of competition

210

Answer

: World of competition

270

Test-1

: Hydrocarbon & Benzene derivatives

272

Answer

: Test-1

282

Unit 4 : Alkyl halide, alcohol & ether

283

Exercise 01 : Subjective approach

284

Answer

385

: Subjective approach

Exercise 02 : Objective approach

290

Single correct questions (SCQ)

290

Multiple correct questions (MCQ)

341

Assertion/reason type questions (A/R) 348

Answer

Match the column type ques. (MTC)

350

Comprehension type questions

352

Integer type questions

356

: Objective approach

(vi)

397

Exercise 03 : World of competition

360

Answer

: World of competition

400

Test-2

: Alkyl halide, alcohol & ether

402

Answer

: Test-2

413

Unit 5 : Aldehyde, Ketone, Carboxylic acid


414

and Derivatives
Exercise 01 : Subjective approach

415

Answer

484

: Subjective approach

Exercise 02 : Objective approach

424

Single correct questions (SCQ)

424

Multiple correct questions (MCQ)

442

Assertion/reason type questions (A/R) 446

Answer

Match the column type ques. (MTC)

449

Comprehension type questions

452

Integer type questions

458

: Objective approach

507

Exercise 03 : World of competition

461

Answer

: World of competition

509

Test-3

: Aldehyde, Ketone, Carboxylic acid


and Derivatives

Answer

: Test-3

510
521

Unit 6 : Biomolecules, Polymer, POC and


522

Physical properties
Exercise 01 : Subjective approach

523

Answer

578

: Subjective approach

Exercise 02 : Objective approach

525

Single correct questions (SCQ)

525

Multiple correct questions (MCQ)

540

(vii)

Assertion/reason type questions (A/R) 545

Answer

Match the column type ques. (MTC)

547

Comprehension type questions

549

Integer type questions

551

: Objective approach

588

Exercise 03 : World of competition

554

Answer

: World of competition

590

Test-4

: Biomolecules

592

Test-5

: Reduction, Oxidation, Hydrocarbon, &


Derivative, Alkyl halide alcohol & Ether 603

Test-6

: Reduction, Oxidation, Hydrocarbon &


Derivative, Alkyl halide alcohol & Ether 613

Test-7

: Aldehyde, Ketone, Carboxylic acid


and Derivatives

624

Test-8

: Mixing of chapters in organic reactions 635

Answer

: Test-4, 5, 6, 7, 8

645

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(viii)

Alkene & Alkyne

Unit

Alkene and Alkynes

Objective
This unit give you a n understa nding of Genera l
Orga nic chemistry of alkene & Alkyne and covers
following topics:
Reaction of HX
Reaction of H2 O/H+
Reaction of ROH/H+
Reaction of X2
Reaction of X-X
Reaction of NOX
Reaction of HOX
Oximercuration-Demercuration
Alkoxymercuration-Demercuration
Hydroboration-Oxidation

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Alkene & Alkyne

Exercise

01
Subjective Approach
You cant learn organic chemistry because theres too much of
it. You can learn trivial things like name of compounds but that
doesnt help you to understand the principle behind the subject.
You have to understand the principle because the only way to
tackle organic chemistry is to learn to work it out. That is why we
are first providing you some questions so that your understanding
about the topic should be increased. These problems should be set
you on your way but they are not the end of the journey as you
begin your journey to understand organic chemistry.
The problem would be of little use to you when you could not
check your answers. For the maximum benefit, you need to solve
all the problems without looking the answers. Then you should
compare your answers or suggestions with ours before going to
next chapter. If any answer is mismatch then darken those question
numbers with red pen and again have a micorscopic look over it
and its theory and correct it before proceeding further. Here starts
the first set of 55 questions
1. What are the general types of organic reactions. Comment over
it by taking simple alphabets without any reaction.
2. Wha t is rea gent. Na me the types of reagent generally we
encounter in organic chemistry.

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3. What is a n electrophile a nd what a re the fa ctors which
increases the electrophilic nature of any molecule.
4. What is nucleophile and what a re the factors which Increases
the nucleophilic character of any molecule.
5. What is free radical and what a re the factors which increases
the free radical formation easy in a ny molecule.
6. What is leaving group and what are the factors which increases
the leaving group character of a ny species.
7. Write the order of nucleophilic character in given molecule.
O
O
OH , PhO , CH 3 CO , CH 3 SO
I , Br , Cl , F

O
NH 3 , H 2 O

8. Write in decreasing order of leaving group character in given


molecules.
O
O
OH , PhO , CH 3 CO , CH 3 SO

I , Br , Cl , F

O
NH 3 , H 2 O

9. What are solvents. How they are classified. Write example of


each types.
10. What is the basic difference between base, nucleophile and
ligand. Explain with example.
11. What is the general chemical reaction of alkene & alkyne.
12. What is Markownikoff rule.
13. What is the basic concept behind Markownikoff rule. Give an
example which violate this rule.
14. Write 2 chemical test which can distinguish alkene from alkanes.
15. What is Baeyers reagent. How is it importa nt in organic
chemistry.
16. Wha t is genera l hydra tion rea ction of alkene. Give the
mechanism of hydration of propene.

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17. What are the three methods by which water is added to alkene.
18. What is oximercuration-demercuration. Explain with an
example.
19. What is alkoxymercuration-demercuration. Explain with an
example.
20. What is hydroboration-oxidation. Explain with an example.
21. Comment on the nature of hydroboration-oxidation and state
whether it follows Markownikoff rule or violate it.
22. Write the mechanism of bromination of alkene using propene
as substrate.
23. What type of change in product is observed when bromination
is carried out in different conditions such as
(A) Br2 / CCl 4

(B) Br2 /H 2 O

(C) Br2 / NaCl

(D) Br2 / CH 3OH

Write the reaction using propene as substrate.


24. Write the reaction as well as mechanism of addition of HBr on
alkene, taking propene as substrate.
25. Write the reaction as well as mechanism of addition of HOCl
on alkene, taking propene as a substrate.
26. Write the reaction as well as mechanism of addition of ICl on
alkene, taking propene as a substrate.
27. Write the major product of following reactions.
8

7
ICl

HOCl

Br2 /CCl 4

HCl
H2 O/H+

Br2 /H2 O

ii) (Ac2O)Hg/H2 O
ii) NaBH4
i) BH3
ii) H2 O 2 /OH

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28. What is Kharasch effect or Anti-Markownikoff rule. Explain
with an example taking propene as a substrate.
29. What is NBS. Write the product formed on reaction on propene
with it.
30. What is NCS. Write the product formed on reaction of propene
with it.
31. What product is obtained when propene is hea ted with
chlorine at high temperature.
32. What will be the major product obtained on reaction of NBS
over following substrate.
(A) But-1-ene
(B) 3-Methylcyclohexene
(C) Penta-1,4-diene
(D) Cyclohexa-1,4-diene
33. Write the reaction as well as mechanism of addition of HCl on
alkyne.
34. Write the reaction as well as mechanism of addition of HOCl
on propyne.
35. What will be obtained as a product when propyne undergoes
hydroboration-oxidation reaction.
36. How general hydration of alkyne occur. Give reaction as well
as mechanism of it taking propyne as substrate.
37. What is the role of mercury sulphate in hydration reaction of
alkyne along with dilute sulphuric acid.
38. What will be the major product obtained when compound
ha ving conjuga tion of a lkene & a lkyne such a s
pent-1-en-3-yne is treated with 1 eq. of HCl.
39. What will be the major product obtained when compound
having double bond & triple bond are not is conjugation such
as pent-1-en-4-yne is treated with 1 eq. of HCl.
40. Why alkenes are generally more reactive than alkyne towards
any electrophilic addition reaction.
41. Why some acids are added to the reaction chamber before
adding water in the hydration reaction of alkene & alkynes.

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42. What is the major product of hydroboration oxidation reaction
of following compounds.
CH3
|

i) B2H6
(A) CH3 CH CH = CH 2
X
ii) H2O 2 /OH
CH3
|

i) B H

2 6
Y
(B) CH3 CH C CH
ii) H O /OH
2

43. What is the major product of oximercuration-demercuration


of following compounds.
CH3
|

i)(Ac 2O)Hg/H2O
(A) CH3 CH CH = CH2
X
ii)NaBH4

CH3
|

i)(Ac 2O)Hg/H2O
(B) CH 3 CH C CH
Y
ii)NaBH 4

44. Write the product of bromination in different condition.


Br2 /CCl 4
Br2 /H 2 O
Br2 /CH3 OH

M
N
O

Br2 /NaCl

P
45. Write the major product of following reaction.

HCl

i) B 2H 6

i) B2 H 6
ii) CH 3COOH

O
C

O 2
H2
g/
) H BH 4
Br2
O
a
2
c
A i i) N
)i (

ii) H 2O 2 /OH
ICl

H 2O/H +/Hg 2+

46. How terminal alkyne is distinguish from non-terminal alkynes.

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47. What product will be formed when acetylene (HC CH) is
heated with Fe?
48. Why the acid catalysed hydration of following alkene follows
>

the same order as that of stability of it.

>

49. Why electrophilic addition of 1,3-Butadiene is faster than that


of But-1-ene.
50. Write the structures of total isomers (including stereo) formed
when one quivalent of HBr is added to Buta-1,3-diene.
51. Write the structures of total isomers (excluding stereo) formed
when one equivalent of HBr is added to Hexa-1,3,5-triene.
52. What will be the product of bromination of following substrate.
H

OH

OH

(D) N
H
53. What will be the major product of acid hydration in given
compounds.
N

(A)

(B)

(C)

(A) H 2 C = C = CH2

(B)

(C)

(D)

54. Write the mechanism of following interconversion.


OH
Ph CH C CH

H 2O /H +

O
Ph CH = CH C H

55. Write the ma jor product of protona tion in following


compounds.
O
O
(A)

(B)

OH

(C)

HO

(D)
Ph

Ph

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Exercise

02
Objective Approach
Single Correct Questions (SCQ) :
1.

CH2 =CH2
I

CH3 OCH=CH 2
II

ClCH=CH 2
IV

OHCCH=CH 2
V

CH 3 CH=CH 2
III

Correct order for electrophilic addition reaction of given


compound follows
(A) I > II > III > IV > V
(C) II > IV > III > I > V

(B) II > III > I > IV > V


(D) V > IV > II > III > I

Cl

CH 3

2.
I

II

III

IV

V
Correct order for electrophilic addition reaction of given
compound follows
(A) I > II > III > IV > V
(B) III > V > II > IV > I
(C) III > IV > V > II > I
(D) I > IV > III > II > V

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Ph

3.

Ph

PhCH=CHPh
II

PhCH=CHCH 3
III

CH3 CH=CHCH 3
IV

Correct order for electrophilic addition reaction of given


compound follows
(A) I > II > III > IV

(B) I > III > II > IV

(C) I > II > IV > III

(D) II > I > III > IV

4. H 2 C=CH 2 CH 3 CH=CH 2 CH 3 C=CH2


|
I
II
CH3
II

CH 3 C = CCH 3
|

CH3 CH3
IV

Correct order for electrophilic addition reaction of given


compound follows

5.

(A) IV > III > II > I

(B) I > II > III > IV

(C) III > IV > II > I

(D) IV > II > I > III


Cl

CH=CH2

CH 3
I

CH=CH 2
II

CH 3 O

O2N

CH=CH 2
III

CH=CH2
IV

Correct order for electrophilic addition reaction of given


compound follows

6.

(A) III > I > II > IV

(B) IV > II > I > III

(C) III > II > I > IV

(D) IV > III > II > I

IV

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Correct order for electrophilic addition reaction of given
compound follows
(A) I > II > III > IV

(B) I > II > IV > III

(C) II > I > IV > III

(D) II > IV > III > I

7. Incorrect order of reactivity towards electrophilic addition


reaction of following compound follows
(A) Ethene > Propene
(B) Methoxyethene > Chloroethene
(C) Phenylethene > Cyclohexylethene
(D) Ethene > Ethyne
8.

CH3 OCH=CH 2
I

FCH=CH2
II
CH=CH2

CH3CH=CH2
III

IV
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

CH3
CH2=CH2 CH2=CHCHO CH3CH 2CH=CH2 CH C=CH
9.
3
2
I
II
III
IV
Rate of addition of Cl2 / H2O of the following alkenes is

(A) IV > III > I > II


(C) I > II > III > IV

(B) IV > III > II > I


(D) I > II > IV > III

10. Which of the following reactant is most reactive towards


electrophilic addition reaction with HBr.
(A)

(C)

10

Ph

Ph

Ph
Ph

(B)

OCH3

(D)

CH 3

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HBr Major product

11.

CH2Br

(A)

(B)

CH 3
Br

CH3

Br

(C)

Br

(D)

HCl

Major product

12.

H
CH 2CH2Cl

ClCCH3

(A)

(B)

Cl

CH2CH3
CH2CH3

(C)
13.

(D)
CH=CH
CHCH 2

(A)

Br

HBr

Cl

Major product
(B)

CH 2CH
Br

Br

Br

(C)

CH=CH

(D)

CH=CH

14. F3C CH = CH2 + HCl Major product


H

(A) F3 CCCH 3
Cl
(C)

F3CCHCH 2
Cl

Cl

(B) F3C CH2 CH3

(D) F3CCH2CH2Cl

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CH 2
HBr

15.

X
(major product)

X will be
CH 2 Br

(A)

(B)

CH 3

(C)

CH 3
Br

CH 3

Br

(D)
Br

16. Major product X, Y, Z obtained in the following reaction is:


CH3

HBr
H2O

HBr
CH 3OH

HBr
D 2O

(A)

OH
CH 3
,

OD
CH 3
,

OCH 3
CH 3

(B)

OH
CH 3
,

OCH 3
CH3

OD
CH 3

Br

(C)

(D)

12

CH 3

OH
CH 3

in all reaction

in all reaction

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17. Which of the following is/are the major product(s) of the
following reaction?
CH 3
CH= C

HBr

CH3

CH 3

CH=CH

(A)

CH2 C
Br

(B)

Br

CH 3

CH 3
CH=C

(C)

CH=C

(D)

Br

Br

18. In which of the following alkenes will a hydrogen shift occur


upon addition of HBr?
(A)

(B)

(C)

(D)

19. The product of following reaction can be :


OH

HBr

CH=CH 2

H3 C

CH 3

(A)

H3 C

OH

OH

(B)

CH3

CH 3

CH 3
H3 C

(C)

O
CH2

(D)

O
CH 3

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HCl
20. PhCH=CHCH 3

The major product of given reaction will be


Cl
(A) PhCH CH=CH
2
3

(C)

Cl

(B)

CH=CHCH3
Cl

PhCHCH 2 CH 3

(D) Cl

CH=CHCH3

CH 3

21.

HBr

CH2 Br

(A)

(B)

CH 3
Br (C)

CH 3

(D)
Br

HCl

22.
CH 3

X
(major product)

(A)

(B)
CH 3Cl

Cl

(C)

Cl

(D)
Cl

CH3
HCl

23.
OH

X
(major product)

Major product X will be


Cl

Cl

(A)

(B)
Cl

Cl

(C)

14

(D)

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Br

Alkene & Alkyne


24. Which of the following reaction results in the formation of pair
of enantiomers on treatment with HBr
(A)

(B)

(A)

(B)

(C)

(D)
O
25. Which of the following reaction results in the formation of a
pair of diastereomers on treatment with HBr
(C)
(D)
Ph
26. How many transition state and intermediate will be formed
during the course of following reaction.
Br
HBr

(A) 3 TS & 3 intermediate

(B) 4 TS & 3 intermediate

(C) 3 TS & 2 intermediate

(D) 3 TS & 4 intermediate

Et
Me

27.

HBr

The product(s) of the following reaction can best be


(A) A racemic mixture
(B) A single enantiomer
(C) A pair of diastereomers

(D) A single meso compound

Cl

28.

HCl

The major product X in the given reaction will be


(A) cis-1,3-Dichlorocyclohexane
(B) trans-1,3-Dichlorocyclohexane
(C) cis-1,2-Dichlorocyclohexane
(D) trans-1,2-Dichlorocyclohexane

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Alkene & Alkyne


29. Which reaction will occur at the fastest rate.
HBr

Br

HBr

(A)

(B)
Br

(C)

HBr

Br
HBr

(D)

Br
30. Predict the major product of the reaction of 1,4-pentadiene
with excess HBr.

(A) 1,4-dichloropentane

(B) 1,5-dichloropentane

(C) 2,4-dichloropentane

(D) 4-chloro-1-pentene

31. Which energy dia gra m best describes the electrophilic


addition of HBr to alkenes?
(A)

(B)

(C)

(D)

32. Which reaction has the lowest G or activation energy?


(A)

HBr

(B)

HBr

(C)

HBr

(D)

HBr

HCl

33.

Cl

The intermediate formed in given reaction will be


(A)
34.

(B)

(C)

(D)

Cl

HCl

The carbocation which is not formed at all in given transformation reaction is


(A)

16

(B)

(C)

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(D)

Alkene & Alkyne


HCl

35.

Which reaction mechanism is most likely to occur during this


reaction.
Cl

H+

(A)

Cl

Cl

(B)

H+

(C)

(D)

Cl

Cl

H+

Cl

Cl

Cl
H+

36.

Which of the following energy profile best represents above


reaction

Ep

Ep

(A)

(B)
Overall reaction

Overall reaction

Ep

Ep

(C)

(D)
Overall reaction

Overall reaction

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37. What is/are the product(s) from the following reaction?
CH 3
+ HCl

CH 3
Cl

CH 3

Cl

(I)

(A) I only

(B) II only

(C) I is minor, II is major

(D) I is major, II is minor

dil.H SO

38.

4
2

CH 3

HO

OH

OH (B)

(A)
39.

(II)

(C)

OH (D)

dil.H SO

2
4

X
(major product)
Major product X is :

CH 3

CH 3
OH

(A)

(B)
OH
OH

OH
CH 3

(C)

dil.H 2SO 4

40.

CH 3

(D)

CH=CHCH3

X
(major product)

Major product X will be :


(A) only

(B) only
CH2CHCH3
OH

(C) (A) and (B)

18

CHCH 2CH3
OH

(D)

OH
CH2CH 2CH3

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dil.H 2 SO 4
41. Ph CH2 CH = CH2

(A)

(C)

PhCHCH 2 CH 3
OH
PhCHCHCH 3

(B)

PhCHCHCH 3
H

OH

(D) Ph CH2 OH

OH OH
H 2O/H +

42.

The intermediate formed in given reaction will be


(A)

(B)

(C)

(D)

OH

H
dil.H SO

43.

2
4

NO 2

(A) HO

OH

(B)

NO 2

NO2

HO

OH

(C)

(D)

NO2

44. CH 3 CHCH=CH 2

NO 2

dil. H 2SO 4

CH3

OH

(A) CH 3 CCH 2 CH 3

(B)

CH 3

CH 3

CCH3

CH3 H

CH 3 CHCH 2 CH2 OH

(C)

CH 3 C

OH

(D)

HOCH 2 CH

CHCH3

CH 3 H

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CH 3

45.

CH 3 Br
2

C=C

(X) Product. Value of X is:

(A) 0

(B) 1

(C) 2

(D) 3
H+

46.

CCl 4

HO

X
(major product)

Major product X will be


(A)

(C)

OD

(B)

H 2 O/H +

48.

CH 3

OH

X
(major product)

(A)

(D)

OH
D2O/H +

47.

(B)

CH 3

OD

(C)

OH

(D)

X
(major product)

The major product X of the given reaction will be


OH

(A)

(C)

20

OH

(B)

OH

(D)

OH

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OH

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49. Which of the following is among the major products of the
reaction of (E)-3-methyl-2-pentene with BH3 in THF followed
by the addition of H 2O2//HO ?
OH
H

Et

(A) H

Me

(B)

Me
H

(C) H

Et
Me

OH

(D) Et

Me
Et

50.

Me

Me
Me

OH
H

OH
Me

OCH3

(A) CH3 OH / H+

(B) CH3 CH2 OH / H+

(C) H2 O / H+

(D) HOCl / H+

x
CH 3 CHCH2 CH3 x will be :
51. CH3 CH = CHCH3

OCH 2 CH3

(A) CH3 OH / H+

(B) CH3 CH2 OH / H+

(C) H2 O / H+

(D) HOCl

52. CH
3

(A)

(C)

C=C

Br2

C(CH3 )2 CH 2 OH CCl 4

Br
CH 3
CH3

CH 3

(B)

CH 3

Br
CH 3
O CH 3

(D)

(A). Product (A) is:

Br
H
CH 3 O

CH 3
CH 3

O Br

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CH3
H (1) BH 3 ;THF

53.

(A); Product of the reaction is:

(2) H 2O 2 , HO

(A)

CH 3
H
H
OH
CH 3

54.

CH3
OH
H
H

(B)

(C)

CH 3OH/H

CH 3

H3 C

CH 3
H
H
H

CH 3
H
H
CH 3

(D)

X
(major product)

The major product X will be


CH 3

CH 3

O
(A) H C
3
OCH3

CH 3

(C)

(B)

CH 3

H3 C

OCH3

OCH 3

CH 3

OCH3

(D) H3 CO

H3 C

55. PhCH=CHCH3

CH 3OH/H +

OCH3

CH 3

X
(major product)

The major product X will be


(A)

(C)

22

PhCH2 CHCH 3
OCH3
PhCH2 CH 2 CH 2
OCH3

(B)

PhCHCH 2 CH 3
OCH 3

(D) H3 CO

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CH 2 CH2 CH 3

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56. What is the major product of the following reaction?
CH 3

Br2

H 2O

X
(major product)

The major product X will be


CH 3
Br
(B)
OH

(A)

CH 3

CH 3
Br (D)

OH (C)
Br

CH 3
OH

57. Which reaction intermediate is formed when Br2/CCl4 reacts


with cyclohexene?
Br

(A)

(B)

Br

(C)

Br

(D)

Br

Br /H O

2
2
58. cis-2-Butene

CH 3
CH 3
CH 3
CH 3
H
H
OH
OH
H3 C
H
C
OH
3
Br
Br
H (C) Br
(A) H
(B) Br
H (D) HO
H
CH3
CH3
H
H

Br2
CCl 4

59.
H

Product of above reaction is:

(A) meso

(B) racemic mixture

(C) diastereomer

(D) structural isomer

60.

Br2

Br

Br

(A)

(B)
Br

Br

Br

(C)

Br

(D)

Br Br

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61. What is/are the product(s) from the following reaction?
+ Br2 /CCl 4

Br

(I)

(II)

Br
Br

(III)

Br

(IV)

Br

(A) I and II

(B) I and III

Br

Br

Br

(C) I and IV

(D) II and III

H
N

62.

Br2

X
(major product)

Major product X will be


H

Br

(A)

(B)
Br

(C)

Br2

(D)
Br

Br

Br

OH

63.

Br

Br

X
(major product)

Major product X will be

(A)

Br

Br Br

(B)

OH

Br

(C)

Br

(D)

64. Which compound on reaction with bromine give meso-2,3Dibromobutane as a product.


(A)

24

(B)

(C)

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(D)

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CH 3

65.

Br2

C2H 5

CCl 4

(Z)

Br

Br

(A)

H
Br

Br

Br

Br

H
Br
Br (C)
Br (D) H C
Br
(B) Br
3
C2H 5
H5 C 2 H
H5 C 2 Br
H5 C 2 Br
CH 3
CH 3
CH 3
H
Br2
CCl 4

66.

(stereoisomer)
( )

Identify products:
Et

Et
Br

(A)

Br
Br

(B)

Br

Br
Et

Br

(C)

Br
Br

(D)
H

67. Which of the following is most reactive toward bromination?


(A)

OCH3

(B)

(C)

(D)

CH 3

68.

H
C=C

(A) 0

Cl

CH3

Br2
CCl 4

(B) 1

(X) products. Value of X is:


(C) 2

(D) 3

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69. Which of the following species is an intermedia te in the
reaction shown below?
Br

Br2 /H 2O

OH

(A)

(B)

Br+

Br2(1 eq)

70.

(C)
O

NH 2

(D)

O
H

X
(major product)

Major product X will be


Br
N

(A)

(B)

Br

Br

(C)

(D)

NH 2
Br2 (1 eq)

71.

Br

OH

Br
NH2

X
(major product)

Major product X will be


Br

Br

(A)

OH Br

(B)
OH

Br

(C)

26

(D)

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Br

Br

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COOH

Br2

72.

X
(major product)

Major product X will be


O

O
O

(A)

(B)

Br

Br

COOH

(C)

(D)

Br

Br

Br

SO 3H

Br2

73.

X
(major product)

Major product X will be


O

O
S

(A)

O
O

(B)

Br

Br

SO 3 H

(C)

(D)

Br

Br

SO 3H

Br
Cl
OH

74.

(A) CH3 OH / H+

(B) CH3 CH2 OH / H+

(C) H2 O / H+

(D) HOCl / H+

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75. Which statement is correct for iodolactonization reaction
(A) It is the organic reaction that form a lactone by the addition of an oxygen and iodine across a carbon-carbon
double bond.
(B) It is the organic reaction that form acyclic amide by the
addition of an oxygen and iodine across a carbon-carbon
double bond.
(C) It is the organic reaction that form acyclic ester by the addition of an oxygen and iodine arcoss a carbon-carbon
double bond.
(D) It is the organic reaction that form lactum by the addition
of a n oxygen and iodine arcoss carbon-carbon double
bond.
76. The intermediate formed in halolactonization reaction is
(A) Carbocation

(B) Cyclic halonium ion

(C) Carbanion

(D) Free radical

COO
I 2 /NaHCO 3
CH 2Cl 2

77.
CH3 CH 3

X
(major product)

X (major product)
O

O
O

(A)

O
H

IH 2 C

CH 3
CH 3

(B)

(C)

28

O
H

IH2 C

CH 3
CH 3

ICH 2

CH 3
CH 3

(D)

CH 2 I

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CH 3
CH 3

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78. Which is incorrect among these?
COOH

(A) Ph

O
I2 /NaHCO 3

CHCl 3
0C, 6H

COOH

(B) Ph

Ph

I
O

I2
MeCN
0C, 24H

O
Ph

I
(C) Formation of cis product is kinetic product while trans
product is thermodynamic product.

(D) Formation of cis product is thermodynamic product while


trans product is kinetic product.
O

OH
i) NaHCO 3

79.

ii) I2 , KI, 0C

X
(major product)

Major product x will be


O

(B) I

(A)
I

O
O

(C)

(D)
O

80.

OH

Br2
CH 2Cl 2

X
(major product)

Major product X will be


(A) Br

Br

(B) O
(C)
Br
OH

Br (D)

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Br

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81. Which will not be the product of given reaction
OH

(A)

Br2 /H 2O

H
Br

OH
(C) OH

(B)

(D) Br

OH

i) Hg(OAc) 2 /H 2O
ii) NaBH 4

82.

H
Br

OH
OH

The intermediate of reaction will be

(A)

(B)
O

(C)

HgOCCH 3

(D)

HgOCOCH 3

83. Which of the following sta tement is wrong a bout


oxymercuration-demercuration reaction of alkene.
(A) In 1 st step, Hg(OAc)2 & H2O adds to C=C double bond.
(B) In 2 nd step, NaBH4 reduce HgOAc group & attached H.
(C) The net reaction is a ddition of wa ter according of
markownikoff rule.
(D) Carbocation is formed in this reaction.
CH 3 CHCH=CH2

84.

CH3

(i) Hg(OAc)2 /H 2O
(ii) NaBH 4

OH

(A)

CH 3 CCH 2 CH 3

(B)

CH 3

(C)

30

CH 3 CHCH 2 CH2 OH
CH3

CH 3 C

OH
CCH 3

CH 3 H

(D)

HOCH2 CH CH 2 CH3

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CH 3

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(1) Hg(OAc)2 /THF H 2O

85.

(2 ) NaBH 4 + OH

(A)

(B)
OH

OH

(C)

(D) all of these

OH
CH 3
CCH=CH2

86.

(1) Hg(O 2CCH 3 )2 , H 2 O


(2 ) NaBH 4 + NaOH

CH3 H
C C CH3

(A)

CH3 H

OH

CH3 H
C C CH3

(C)

C
H

(B)

C CH3
H

CH3
CCH2 OH

(D)

CH3

OH H
Hg(OAc)2 /H 2O
NaBD4

87.

OH

(A)

H H
D

(B)

OH

H OH
D

OH i ) Hg (OAc)2

88.

ii) NaBH 4

(C)

OH

H (D)

X
(major product)

Major product X will be


OH

(A)

(B)

(C)

(D)

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OH

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89. Which of the following alkene will give Methylcyclohexanol
on oxymercuration-demercuration
reaction.
(A)

(B)

(C)

(D)

O
Hg(OAc) 2 /ACOH

90.

X
(major product)

Major product X will be

O
HgOAc

(A)

OAc

(B)

OAc
HgOAc

O
OAc

(C)

(D)

HgOAc

HgOAc
OAc
(i) BH3 THF

91.

(ii) H2O2/OH -

(A)

CH3HO

CH 3

(B)
H

HO

H
OH

(C)

CH3 H
H

32

OH

(D)

CH3 H
H

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92. CH 3 CHCH=CH 2
CH3

(i) BH 3 THF
(ii) H 2O 2 /OH

OH

(A) CH 3 CCH 2 CH 3

(B) CH 3 C

CH 3

(C)

CH 3 CHCH 2 CH2 OH
CH3

OH
CCH 3

CH 3 H

(D)

HOCH2 CH CH 2 CH3
CH 3

93. Hydroboration oxidation reaction of alkene follows via


(A) Formation of 6 membered cyclic tranition state.
(B) Formation of 5 membered cyclic transition state.
(C) Formation of 4 membered cyclic transition state
(D) Formation of 3 membered cyclic transition state
(i) BD 3 THF
(ii) H 2O2 / OH

94.

(A)

H H
D

(B)

OH

H OH
D

H
OH

(C)

H H

(D)

H OH

BH 3 , THF

95.

H 2O 2 , OH

(A)
(C)

OH

(B)
OH

(D)

OH

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BD 3 /THF

96.

H 2O 2 /OH

(A)

(C)

X
(major product)

(B)

D
D

(D)

OH

X will be

OH
D
H
OD

X
OH

97.
Y

OH
Z
OH
X, Y, Z reactions are respectively called as

(A) All is simply hydration reaction.


(B) Acid hydra tion, Oxymercura tion-demercura tion,
Hydroboration-oxidation.
(C) Acid hydration, Hydroboration-oxidation oxymercuration
demercuration.
(D) Oxymercura tion-demercura tion,
oxidation, acid hydration.
98.

CH 3 CHCH=CH 2

HBr
20C

HBr
40C

Br (A)
Both the major product A and B are

Hydrobora tion-

CH3CH=CHCH2Br
(B)

(A) Kinetically controlled product


(B) Thermodynamically controlled product
(C) A is thermodynamica lly controlled & B is Kinetically
controlled.
(D) A is kinetically, B is thermodynamically controlled

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HCl (1 eq)

99.
Cl

Cl

(A)

(C)

(B)

(D)

Cl

Cl

100.

HBr / R2O 2

CH=CH
CHCH2

(A)

(B)

CH 2 CH

Br

Br

Br

Br

CH=CH

(C)

(D)

CH=CH

101. What is the major product of the following reaction?


CH 3

HBr
Peroxide

Br

(A)

CH 3

(B)

CH 3

(C)

(D)
Br

CH 2 Br

CH 3
Br

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102. Which of the following is a step in the mechanism of the
reaction shown?
CH 2 =CHCH 3 + HBr

Peroxide

CH 2 CH 2 CH 3
Br

(A)

(C)
103.

CH 2 CHCH 3 + HBr
Br

CH 2 CHCH 3 + HBr
Br

(B)

CH 2 CH 2 CH 3 + HBr

(D) CH 2 CH 2 CH 3 + HBr

I Cl

The intermediate of given reaction will be


(A)
(C)
104.

(B)

Cl

Cl

(D)

HOCl

The intermediate of given reaction will be

(A)

(B)

Cl

(C)
105.

Cl

(D)

OH

NBS

The intermediate of given reaction will be


(A)

36

(B)

(C)

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(D)

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106.

NOCl

The intermediate of given reaction will be


(A)

(C)

(B)

NO

NO

(D)

Cl

107.

ClCN

The intermediate of given reaction will be


(A)

(C)

(B)

Cl

CN

(D)

Cl

NBS
108. CH 3 CH=CH 2

(A) CH 3 CH2 CH 2 Br

(B)

CH 2 CH=CH 2
Br

(C) CH 3 CHCH 3
Br

(D) CH 3 CHCH 2
Br

Br

Cl /CCl

2
4
109. trans-2-pentene

CH 3
H
Cl
(A) Cl
H
C2H 5

CH 3
CH3
CH3
H
Cl
H
C 2 H5
H
C 2 H5
(B) H
Cl (C) Cl
(D) Cl
H
H
C2H 5
H
Cl

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110. Predict the product of the reaction of 1-pentyne and excess
HCl in the presence of hydrogen peroxide.
(A) 1,1-dichloropentane

(B) 1,2-dichloropentane

(C) 2,2-dichloropentane

(D) 2-chloro-1-pentene

OH

111.

CH 3CHCH 2 CC
CH3

(A)

CH

H 2O.H 2SO 4
HgSO 4

CH3

CH 3 CHCH 2 C=CHCH
CH 3

CH3

OH O

(B)

CH 3 CHCH 2 C
CH 3

CCH 3

CH 3
OH

(C)

CH 3 CHCH 2 C C=CH 2
CH 3

CH 3 OH
OH

(D)

CH 3 CHCH 2 CCH=CH
CH 3

CH 3

OH

BH3 , THF
H2O 2 /OH
112. CH 3 CH 2 CH 2 C CH

(A) CH3 CH2 CH2 CH2 CHO

(B)

CH 3 CH 2 CH 2 CCH2
O

(C) CH3 CH2 CH2 CHO

(D) CH 3 CH 2 CCH2 CH 3
O

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Br2 (1 eq.)

113. CH2 = CH CH = CH CH = CH2

(6080C)

X
Major

(A) BrCH2 CH=CHCH(Br)CH=CH 2


(B)

BrCH 2 CH=CHCH=CHCH 2 Br

(C) CH2 =CHCH(Br)CH(Br)CH=CH2


(D) BrCH2 CH(Br)CH=CHCH=CH 2
HCl (1 eq)

114.
(A)

Cl

(B)

115. C3 H7 C CH

Cl

HBr
peroxide

(C)

Cl

(D)

Cl

X X is -

(A) C3 H7 CH = CHBr

(B) C3 H7 CBr = CH2

(C) C 3 H 7 CBr C Br

(D) C3 H7 CH2 CHBr2

116.

CH
Br2 , H 2O

Br

O
C

(A)
Br

(C)

CH

CH 2 Br2

(B)

Br

CH
C

(D)

Br

CH

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MeOH
H 2SO 4

117. CH2 = CHCHOHCH = CHMe

(A) CH2 = CHCHOHCH2 CH(OMe)Me


(B) CH2 = CHCH = CHCH(OMe)Me
(C) CH2 = CHCH = CHCH2 Me
(D) CH3 CH (OMe) CH = CHCH(OMe)Me
118. What is the kinetic product for the following reaction?
CH 3
+ HCl
?
CH 3
Cl
CH 3
Cl
CH 3
(A)
(B)
(C)
(D)
CH 3
Cl
Cl
119. What is the major organic product of the following reaction?
Hg 2+

CH H SO
2
4

(A)

(B)

OH
H

(C)

H
O

(D)

H
HO

120.What reagents can best be used to accomplish the following


transformation?
OH

(A) 1. BH 3 , THF 2. HO , H 2 O 2
(B) H , H 2 O
(C) 1. Hg(OAc)2 , H 2 O/THF 2. NaBH 4
(D) 1. Hg(O2 CCF3 )2 , CH 3OH 2. NaBH 4

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Multiple Correct Questions (MCQ) :


121. The a lkenes which a re more rea ctive than ethene for
electrophilic addition reaction are
(A) CH2 =CHCl

(B) CH3 OCH=CH 2

(C) CH3 CH=CH 2

(D) CH2 =CHCHO

122. Which of the following compounds will give same major


product on acid catalysed hydration
CH 3

(A)

CH 3

PhCCH=CH 2

PhCHC=CH 2

(B)

CH 3
CH 3

(C)

Ph

C=C

CH 3
Ph

CH 3

CH 3

(D)

CH 3

CH 3

CH

C=CH 2

123. The correct products have been reported in reactions.


(A)

(B)

CH 2 =CHCHO

(H Cl(g)(10C)

Cl

CH 2 =CHCOOH

H 2 O/H 2 SO 4

CH 2 CH2 COOH
OH

CH 3

(C)

CH 2 CH 2 CHO

CH 3 C=CHCCH 3

CH 3OH
H 2SO 4

CH 3
CH3 CHCH C CH 3

(D)

CH 3 CH=CHOCH3

OCH3 O
CH 3OH/H +

CH 3 CH2 CHOCH3
OCH 3

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124. Three different alcohols (E), (F) and (G) are synthesised from
the same alkene (P) by using three different reagents (I), (II)
and (III) respectively as shown below. Identify the reagents.
(I)

(E)

CH(OH)CH2 D
(P)

CH=CH 2

(II)
(III)

OH (F)
CH2 D
CHDCH 2 OH

(G)

(A) (I) is D+/H2O;


(II) is 1. Hg(OAc)2, THFH2O 2. NaBD4
(III) is 1. THFB2D6; 2. H2O2, OH
(B) (I) is 1. Hg(OAc)2, THFH2O 2. NaBD4
(II) is D+/H2O
(III) is 1. THFB2D6; 2. H2O2, OH
(C) Products (E), (F) and (G) a re formed via free radical,
carbocation and cyclic carbonium ion intermediate respectively.
(D) Products (E), (F) and (G) are formed via mercury-bridged
carbocation, carbocation and four-centre transition state
respectively.
H , H2 O

125.

Possible products of the reaction will be

OH

(A)
OH

(C)

42

OH

(B)
OH

(D)

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Alkene & Alkyne


126. In which of the following reaction(s), major product is formed
by the cyclic intermediate of reactive intermediate?
(A)

+ HCl

(B)

+ Br2 H2 O

(C)

+ (CF3 COO)2 Hg

(D)

H 2O

NaBH 4

+ HBr

127. Which of the following is correct sta tement a bout


oxymercuration-Demercuration(A) In the I st step oxymercuration occurs i.e. wa ter &
Hg(OAc)2 add to double bond
(B) In the IInd step demercuration occurs i.e. NaBH4 reduces
HgOAc group to hydrogen.
(C) The net rea ction is addition of wa ter a ccording to
Markonikoff rule
(D) Rearrangement takes place
128. In which of the following halogen addition reaction, racemic
mixture of products is formed?
(A)
(B)
(C)

+ Br2 CCl 4

FeCl 3

+ Br2 CCl 4

+ Br2 CCl 4

FeCl 3

FeCl 3

(D) CH 3 CH=CH2 + Br2 CCl 4

FeCl 3

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Alkene & Alkyne


129. Consider the following a ddition reaction on a pure
enantiomer of the shown bromoalkene.
CH 3
H
Br + HBr
CH=CH2

Products(s)

What is/are true regarding products of the above reaction?


(A) Four stereoisomers of products of the above reaction?
(B) A pair of enantiomers and a meso-dibromide are formed
(C) Only a pair of diastereomers are formed
(D) One of the product is meso-dibromide
130. Identify the correct statement/statements :
(A) Alkynes are more reactive than alkenes towards EAR.
(B) Alkynes are less reactive than alkenes towards EAR.
(C) Alkynes decolourise Br2 water
(D) Addition of HBr to alkynes in presence of peroxide
proceeds via Anti-Markownikoffs rule
131. When But-2-yne is brominated, P is formed. When But-2-yne
is reacted with HgSO4 + H2SO4, then Q is formed. Which
statement is correct form
(A) P will be 2,2,3,3-Tetrabromobutane
(B) Q will be Butan-2-one
(C) In the formation of P, Cyclic intermediate is formed.
(D) In the formation of Q, Cyclic intermediate is formed.
132. What are the expected product(s) in the following reaction?
hv
+ NBS CCl
4
(NBS=N-bromosuccinimide)

Br

(A)

44

Br (B)

Br

(C)

(D)

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Br

Alkene & Alkyne


133. Predict products(s) in the reaction
+ HBr

Br
H

(A)

(B)
Kinetically controlled

Br

Br
Kinetically controlled

Br
(D) Thermodynamically
controlled

(C) Thermodynamically
controlled

134. The correct statement(s) regarding following reaction is/are


CH2 =CHCH=CH 2 HBr CH 2 =CHCHCH3 CH 2 CH=CHCH 3

Br

Br

II

(A) At 80C, I is the major product


(B) At room temperature, II is the major product
(C) Both of the products I and II a re a lways formed in
comparable amounts
(D) Product I isomerises into II on heating above 40C
135. The correct sta tement(s) regarding 1,2-buta diene(I) a nd
1,3-butadiene, (II) is/are
CH2 =C=CHCH3
(I)

CH2 =CCH=CH 2
(II)

(A) I ha s perpendicular pi planes while II has para llel


pi planes
(B) Both gives the same product on adding 1.0 equivalent at
HBr of 80 C
(C) I gives 2 ,2 -dibromobuta ne while II gives,
2,3-dibromobutane, when reacted with excess of HBr at
very low temperature
(D) Both have same length of C=C double bonds

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136. Addition of water over alkene occur via
(A) H2O/H+
(B) Hydroboration-oxidation
(C) Oxymercuration-demercuration
(D) Alkoxymercuration-demercuration
137. Which statement is/are correct for hydroboration oxidation
(A) It is the addition of water over alkene
(B) It proceeds via formation of 4 membered cyclic TS.
(C) It follows Markowniff rule
(D) Hydrobora tion oxida tion over propene lea ds to
propan-1-ol as major product.
138. In which case carboca tion is not formed a s a reaction
intermediate on reaction over alkene.
(A) Halogenation

(B) Acid hydration

(C) Oxymercuration-demercuration
(D) Hydroboration-oxidation
139. In which case product is correct.
Cl

(A)

HOCl

NO
NOCl

(B)
OH

Cl

(C)

ICl

CH 3OH
H

(D)

OCH3

Cl

140. In which case rearrnage product will be major one.


(A)
(C)

46

CH 3OH/H

H 2O/H +

(B)

HBr
+

(D)

Ph

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141. 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?

(A) (CH 3 )3 C C HCH2 Cl

(B) (CH 3 )3 C C HCH3

(C)

(CH 3 )2 CC(CH3 )2
|

Cl

(D) (CH 3 )2 C CH(CH 3 )2

142. In the addition of HBr to 1,3-butadiene, one product is called


the kinetic product and the other is called the thermodynamic
product. Which of the following descriptors applies to the
kinetic product?
(A) 1,2 product
(B) least stable with less substituted alkene
(C) formed fastest at low temperature
(D) bromide attack at more substituted site
143. Which of the following a lkenes yield(s) 3 -bromo-3 methylpentane as the major product upon addition of HBr?
(A)

(B)

(C)

(D)

CH 3 CHCH=CH2

144.

(A) H 2 O/H +

CH 3 CHCHCH 3
OH

; Reagent A may not be:

(B) BH 3 .THF/H 2 O 2 OH

(C) Hg(OAc)2 .H 2 O/NaBH 4 (D) BH 3 .THF/H 2 O 2 AcOH

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145. Which series of reactions will not achieve the following transformation?
Br
1

Cl
Cl

(A) Cl 2/CCl4

Br2

(B) HBr

Cl2/CCl4

(C) Cl2/CCl4

NBS/hv

(D) NBS/hv

Cl2/CCl4

COOH

146. HOOC

Br2
CCl 4

(P)

HOOCCH(Br)CH(Br)COOH
(X)

Br

HOOC

2
COOH CCl 4 HOOCCH(Br)CH(Br)COOH
(Q)
(Y)

The correct statements with respect to the above pair of reactions are that
(A) the reactions are stereospecific
(B) (X) is meso and (Y) is racemic mixture
(C) (X) is racemic mixture and (Y) is meso
(D) each of (P) and (Q) gives a mixture of (X) and (Y)
OH

147.

Br2

(A) Br

(C) Br

48

HBr + (P)

Cl

O Cl
P
O OCH
3
Q

MeOH

(Q) product P,Q will be


O

(B)
P

Br

(D)
Q

OCH 3

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148. Select the reaction(s) that would result in the formation of 2bromopropane.
peroxide
(A) CH 3 CH=CH2 + HBr

CCl 4
(B) CH 3 CH=CH2 + HBr

hv
(C) CH 3 CH 2 CH 3 + Br2

CCl 4
(D) CH 3 CH=CH2 + Br2

149. The major product of the reaction given below is :


OH

(A) Br

(C)

Br2
H 2O

OH

(B) HO

OH

(D)

CH 2 Br

Br
OH

CH2 Br
H

150. Which of the following compounds gives the sa me


carbocation on ionization?
(A)

Br

(B)

Br

(C)

Br

(D)

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Br

49

Alkene & Alkyne

Assertion / Reason type Questions (A/R) :


(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
151. Assertion: Addition of HCI to 1 -isopropenyl1
methylcyclopenta ne yields 1 chloro1 ,2 ,
2trimethylcyclohexane.
Reason:

Mechanism of reaction is
CH 3

H+

CH 3
CH 3
and

152. Assertion:

Cl
Cl

CH 3

CH 3
CH3

on hydra tion

give same alcohol.


Reason:

The intermediate carbocation for both the alkenes


is same.

153. 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

154. Assertion: The hydroboration oxidation of


D
D

Reason:

50

gives

OH
D
D

The syn addition of BH3 across the double bond


of norbornane takes place mostly from the more
accesible outside face of the double bond.

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155. Assertion: The addition of chlorine to cyclohexene gives a
racemic mixture of trans-1, 2-dichlorocyclo hexane.
Reason:

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

156. Assertion: Acteylene is less reactive than ethylene towords


electrophilic reagents.
Reason:

pelectron density in a triple bond is higher than


that in a double bond.

157. Assertion: The predominant product in the addition of halogens to acetylene is the trans isomer.
H
I
C=C
Reason: The addition of I2 to acetylene gives
I
H
as the major product.
158. Assertion: When acetylene is passed into hyochlorus acid
solution dichloroacetaldehyde is formed.
Reason:

The process of reaction is


H
HC

CH + HOCl

HC=C

HO
HOCl

ClC CH + H 2O

ClOH

Cl

159. Assertion: 2Bromo1butene reacts with HBr to give 2,2


dibromobutane.
Reason:

The intermediate carbocation formed is stablished


by +m effect of Bromine atom.

160. Assertion: With the use of BD 3 /THF a nd CH 3 COOH,


2-Butyne gives Cis-2-deutero-2-butene.
Reason:

The same product is obtained when the reagent


used is BH3 /THF and CH3 COOD.

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Match the Column type Questions (MTC) :


161. Match the column:
(A)

HBr
Peroxide

(P)

(B)

HBr
No Peroxide

(Q)

Br

(C)

HCl
Peroxide

(R)

Cl

(D)

HCl
CCl 4

(S)

(E)

NBS

(T)

Br

Cl
Br

162. Match List-I with List-II and select the correct answer using
the codes given below the lists:
List-I (Reaction)

List-II (Reagents)

(A) CH 3CH=CH2 CH3CHBrCH3

(P) HBr

(B) CH3CH=CH2 CH3CH2CH2Br

(Q) Br2

(C) CH3CH=CH2 BrCH2CH=CH2

(R) HBr/Peroxide

(D) CH3CH=CH2 CH3CHBrCH2Br (S) NBS


163. Match the column:
(A)

HBr
Proxide

(P)

Electrophilic-addition
reaction

(B)

HCl
Proxide

(Q)

Free-radical-addition
reaction

(R)

Free-radical-substitution
reaction

(S)

Electrophilic
substitution reaction

CH 3

(C)
(D)

52

NBS

Cl 2 /AlCl 3

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164.

Column-I

Column-II
Cl

Cl 2 ,CCl 4

(A)

P.

Rearrangement

Cl
Cl 2 ,hv

(B)
Br

(C)

CH 3OH

(D)

H /H 2O

165.

Cl

OH

Q. Carbocation

R.

Free radical

S.

Cyclic intermediate

Column-I

Column-II

Markownikoff
(A) product

P. CH 3 CH=CH 2 H2O 2 ,hv

Anti-Markownikoff
(B) product

Q.

(C) Peroxide effect

R.

(D)

Mixture of
stereoisomers

HBr

H3 C
H

C=C

CH3 CHCl +KOH


3
H

CH=CH 2 HBr

S. CF3 CH=CH 2 HBr

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Comprehension type Questions :


Passage : 1
In electrophilic addition rea ction, a lkene behave a s a
nucleophile or base. During reaction electrophile react with
a lkene in ra te determining step to form carboca tion
according to markownikoff rule. In second step carbocation
react with nucleophile to give product so overall addition
reaction take place.
166.

+ Br2

CCl 4

Number of product (including stereo) formed in the


reaction:
(A) 1

(B) 2

(C) 3

(D) 4

167. Correct order of rate of Bromination:

(I)

(II)

(III)

(A) I > II > III

(B) II > I > III

(C) III > II > I

(D) II > III > I

Passage : 2
Homolytic bond fission of a covalent single bond gives rise to
free radicals. Owing to the presence of an odd electron, free
radicals are highly reactive. They have planar to pyramidal
geometry depending upon the groups attached to the C-atom
having odd electron. Alkyl free radicals are stabilised by
hyperconjugation whereas allyl and benzyl free radicals are
stabilised by resonance. They are formed as intermediates in
the reaction mixture either in the gaseous phase or in nonpolar solvents. Addition of HBr to alkenes in presence of peroxide, the substitution of allylic or benzylic hydrogen by Cl
at high temperature or by Br in presence of NBS are examples of reactions involving free radical intermediates. Now
answer the following questions :

54

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168. 3,5-dimethylcyclopentene reacts with N-bromosuccinimide
(NBS) in CCl4 in presence of light or peroxide. Identify the
product.
H3 C

CH 3
+ NBS

(A)

(C)

H3 C

hv

Expected Product
H3 C

CH 3
Br

H3 C

CH 3

(B)
Br

H3 C
CH 3
(D)
Br
Br

CH 3 H3 C
Br &

CH 3
Br

169. Arrange the following free radicals in the decreasing order


of their stability.

. .

CH 2 =CHCH2 ; (CH 3 )3 C; CH 2 =CH; CH 3

(A) (CH 3 )3 C > CH 2 =CHCH 2 > CH 2 =CH > CH 3

. .

(B) (CH 3 )3 C > CH 2 =CHCH 2 > CH 3 > CH 2 =CH


(C) CH 2 =CHCH 2 > (CH3 )3 C > CH 3 > CH 2 = CH

(D) CH 2 =CHCH 2 > (CH3 )3 C > CH2 =CH > CH 3


Passage : 3
Addition of HX on alkene proceed through the formation of
carbocation. This reaction is also known as Markownikoff
reaction. According to Markownikoffs rule addition of
electrophile occurs on that carbon of alkene which have more
number of H atom.
X
PhCH=CH 2

HX

PhCHCH 3 + PhCH2 CH 2 X
Major
Minor

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Mechanism :
H

HX
Ph
H

H X

C=CH 2

Ph

CCH 3 + PhCH 2 CH 2
H
More stable
Less stable

Ph

Ph
CCH 3 + X

C
H

X
+

Ph
C

CH 3 H 3C
Enantiomer

170. Which of the following alkene can produce diastereomers ?


(A) CH 3 CH=CHCH3
H

(C)

(B)

CH 3
CH 3

CH=CHCH3

(D) CH3 CH=CH2

171. Which of the following alkenes will give Markownikoff


reaction ?
HCl
(A) F3 CCH=CH 2

HCl
(B) H 3 CCH=CH 2

HBr
(C) O 2 NCH=CH2

(D)

CH 3
CH3

HBr
C=CH 2

Passage : 4
Hydroboration oxidation reaction is a process of addition of
H2O according to Markownikoffs rule but product resemble
Anti-Markownikoff of product.
CH 3CH=CH 2

BH 2.THF
H 2O 2 , OH

CH 3 CH 2 CH 2 OH

Rea ction is regioselective, Regioselectivity of reaction


in increased by using hindered boranes. THF (Tetrahydrofuran) is used to control reactivity of borane.

56

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BD 3.THF

172.

CH 3
D
OH
CH3

(A)

(C)
H

(B)
H

CH 3
OH
D

HOOC

173.

Major product :

H 2O 2 ,OH

(D)
H

C=C

CH 3
D
OH

CH 3
OH
OH
H

BD 3.THF

COOH D 2O 2 ,OH

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

Passage : 5
To predict relative reactivities of various positions in a given
molecule two different methods are generally used.
(i). Predictions based on charge distributions:- This approa ch
assumes that the reactivities of a position in a polar reaction is
determined by the cha rge density at that position, i.e. an
electrophilic reagent will attack preferentially at the site of
highest electron density and a nucleophilic reagent will attack
preferentially at the site of lowest electron density. The charge
distribution is a scerta ined by the exa mina tion of the
consequences of inductive and/or resona nce effect. This
approach is referred to as the isolated molecule method.
(ii). Predictions based on stabilities of intermediates:- This method
assumes that the reactivities of different positions in a given
molecule are determined only by their relative activation

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energies. Since the activation energy depends on the structures
of the transition state. For the reactions that are belived to
involve intermediate carbocation, carbanion and free radicals,
it is these that are chosen to represent the structure of transition
states, the stabilities of which are then examined in terms of
inductive effect and/or resonance effect. The assumption is
then made that the more stable the intermediate (i.e. the lower
its energy), the lower is the energy of TS and consequently the
lower is the energy of activation leading to that intermediate.
This approach is referred to as the localisation energy method.
Based on these methods solve question 174175.
174. In Which molecule attack of electrophile will be easy over
alkene.
(A) CH2 =CH 2

(B) CH2 =CHCl

(C) CH2 =CHOCH3

(D) CH 2 =CHNO 2

175. In which molecule most stable intermediate will be formed


after protonation.

(A)

58

(B)

(C)

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Cl

(D)

Cl

Alkene & Alkyne

Integer type Questions :


176. How many of the following reactions, leads to the formation
of diastereomers.
(A)

H3 C

HCl

Ph

(C)

HBr

C=CH2 CCl
4
H

HBr
CCl 4

(B)

C=CHCH 3 CCl
4
H

(D)

CH3
HCl
D CCl
4
CH
CH
Ph

CH 3

(E)

CH 2

Ph
HCl
CCl 4

HCl
CCl 4

(F)
CH 3

177. Identify number of chiral centers present in product obtained


by following reaction.
Br2
CCl 4

CH 3

178. How many different products (excluding stereoisomer) can


be obtained by following reaction.
HCl, CCl 4

179. If a pure enantiomer of 5-bromo-2-hexene is treated with


Br2CCl4, how many different tribromides would be formed?
180. If a racemic mixture of 3-methyl-1-pentene is treated with
HCl, how ma ny different chloropenta ne (importa nt
products only excluding stereo) would be formed?

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Exercise

03
World of competitions
1. What is the product when acetylene reacts with hypochlorous
acid ?
[AIEEE 2003]
(A) CH 3 COCl
(C) Cl 2 CHCHO

(B) ClCH 2 CHO


(D) ClCHCOOH

2. Rea ction of one molecule of HBr with one molecule of


1,3-butadiene at 40C gives predominantly.
[AIEEE-2005]
(A) 1-Bromo-2-butene under kinetically controlled conditions
(B) 3-Bromobutene under thermodynamically controlled
conditions
(C) 1-Bromo-2 -butene under thermodynamically controlled
conditions
(D) 3-Bromobutene under kinetically controlled conditions
3. Acid catalyzed hydration of alkenes except ethene leads to the
formation of
[AIEEE-2005]
(A) Mixture of secondary and tertiary alcohols
(B) Mixture of primary and secondary alcohols
(C) Secondary or tertiary alcohol
(D) Primary alcohol

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4. HBr reacts with CH2 =CHOCH3 under anhydrous conditions
at room temperature to give
[AIEEE-2006]
(A) CH3 CHO and CH 3 Br
(B) BrCH 2 CHO and CH 3 OH
(C) BrCH 2 CH2 OCH 3
(D) H 3 CCHBrOCH3
5. Acid catalyzed hydration of alkenes except ethene leads to the
formation of
[AIEEE-2005]
(A) Primary alcohol
(B) Secondary or tertiary alcohol
(C) Mixture of primary and secondary alcohols
(D) Mixture of secondary and tertiary alcohols
6. Assertion: Addition of fbromine to tra ns-2-butene yields
meso-2. 3-dibromobutane.
[IIT-JEE 2001]
Reason:

Bromine addition to an alkene is an electrophilic


addition

(A) Assertion is True, Rea son is True, Rea son is correct


explanation for Assertion.
(B) Assertion is True, Reason is True, Reason is NOT a correct
explanation for Assertion.
(C) Assertion is True, Reason is False.
(D) Assertion is False, Reason is True.
HgSO

A
7. C 6 H5 C C CH 3
H2 SO 4

[IIT-JEE 2003]

(A)

(C)

(B)
C 6 H5 C=CHCH 3
OH

(D)

C 6 H5 CH=CCH 3
OH

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8.

On acid catalysed hydration, 2-phenyl propene gives: [JEE 2004]


(A) 2-phenylpropan-2-ol

(B) 2-phenylpropan-1-ol

(C) 3-phenylpropan-2-ol

(D) 1-phenylpropan-1-ol

9. A n organic compound (P), C 5H10O reacts with dil. H2SO4 to


give (Q) and (R). Both (Q) and (R) give positive iodoform test.
The reactivity of organic compound (P) is 1015 times more than
ethylene with respect to dil. H2SO4.
[IIT-JEE 2004]
(i)

Identify the compounds (P), (Q) and (R)

(ii) Give reason for the extraordinary reactivity of compound


10. CH 3 CH=CH 2 + NOCl P

[IIT-JEE 2006]

Identify the adduct


(A)

CH 3 CHCH 2
Cl

NO

(B)

CH 3 CHCH 2
NO Cl

NO

CH 2 CH2 CH 2
(C) CH 3 CH 2 CH
(D)
NO
Cl
Cl
11. The number of stereoisomers obtained by bromination of
trans-2-butene is
[IIT-JEE 2007]
(A) 1
(B) 2
(C) 3
(D) 4
12. The major product of the following reaction is [IIT-JEE 2011]
RCH 2OH
O

H (anhydrous)

(A) a hemiacetal

(B) an acetal

(C) an ether

(D) an ester

13. In the hydroboration-oxida tion rea ction of propene with


diborane, H2 O2 and NaOH, the organic compound formed is:
[IIT-Mains 2014]
(A) CH3 CH 2 OH

(B) CH3 CHOHCH3

(C) CH 3 CH 2 CH 2 OH

(D) (CH 3 )3 COH

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CH2 CH 2 =CH 2 on mercura tion-demercura tion pro-

14.

duces the major product:


CH2 CHCH3

(A)

OH

CH2 CHCH2

(C)

OH OH

[IIT-Mains 2014]
CH2 CH 2 CH2 OH

(B)

CH 2 COOH

(D)

15. In the following reaction, the major product is


CH3

[IIT-Adv. 2015]

CH 2 1 equivalent HBr

CH3

(A) H2 C

CH 3

CH 3

(B)

Br

H3 C Br

CH3

(C)

CH3

H2 C

(D)

Br

H3 C

Br

Comprehension: In the following reactions


C 8 H6

[IIT-Adv. 2015]

i. B H

Pd-BaSO 4
H2

C8 H 8 ii. H2 O6 , NaOH , H O X
2 2
2

H 2O
HgSO 4 , H 2SO 4

C 8 H8 O

i. EtMgBr, H 2O
ii. H + , heat

16. Compound X is:


O

(A)
(C)

OH
CH 3

OH

(B)

CH 3

(D)

CHO

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17. The major compound Y is:
CH 3

(A)
CH2

(C)

CH 3

(B)

CH 3

CH 3

(D)

CH 3

18. Anti-Markownikoff addition of HBr is not observed in :


[CET (J & K) 2012]
(A) 2-butene

(B) 1-butene

(C) propene (D) 2-pentene

19. The negative part of the addendum adds on to unsaturated


carbon atom joined to the least number of hydrogen atoms.
This statement is called:
[AFMC 2004]
(A) Saytzelff rule

(B) Kharasch effect

(C) Markownikoffs rule

(D) Anti-Saytzeff rule

20. When propyne is treated with aqueous H2SO4 in presence of


HgSO4, the major product is:
[PMT (Kerala) 2010]
(A) propanone

(B) 2-propanol

(C) ethanal

(D) ethyne

21. Reaction of HBr with propene in the presence of peroxide gives:


[AIPMT 2004]
(A) isopropyl bromide

(B) allyl bromide

(C) n-propyl bromide

(D) 3-bromopropane

22. Which of the following rea ctions will yield 2 ,2 dibromopropane?


[CPMT 2004]
(A) H2C = CHBr + HBr

(B) CH3C = CCH3 + 2HBr

(C) CH3C = CH + 2HBr

(D) CH3CH = CHBr + HBr

23. Which of the following alkenes will give an optically active


alcohol when treated with H2O/H2SO4?
[CPMT 2004]
(A) 1-Butene

(B) Ethene

(C) Propene

(D) 2-Methyl propene

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24. Acid catalysed hydration of alkenes except ethene leads to the
formation of:
[JCECE (Med.) 2008]
(A) primary alcohol
(B)

secondary of tertiary alcohol

(C) mixture of primary and secondary alcohols


(D) mixture of secondary and tertiary alcohols
25. The only alcohol that can be prepared by the indirect hydration
of alkene is:
[AFMC 2005]
(A) ethyl alcohol

(B) propyl alcohol

(C) isobutyl alcohol

(D) methyl alcohol

26. 3-phenyl propene on reaction with HBr gives (as a ma jor


product):
[AIIMS 2005]
(A) C 6 H 5 CH 2 CH(Br)CH3

(B) C 6 H 5 CHCH(Br)CH 2 CH3

(C) C 6 H 5 CH 2 CH 2 CH 2 Br

(D) C 6 H 5 CH(Br)CH = CH2

27. Trans-2-butene-Br2 gives:

[CET (Gujarat) 2006]

H
(A)
H

CH 3
Br
Br
CH 3

Br
(B) H

CH 3
H
Br
CH 3

Br
(C)
H

CH3
Br
H
CH 3

H
(D) Br

CH 3
Br
H
CH3

28. Reaction of acetylene and propylene with HgSO4 in presence


of HgSO4 produces respectively:
[BHU (Med.) 2006]
(A) acetone and acetaldehyde
(B)

acetaldehyde and acetone

(C) propanaldehyde and acetone


(D) acetone and propanaldehyde

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29. Predict the product C obtained in the following reaction of 1butyne:
HI
CH3 CH 2 C CH + HCl (B)
(C)

[AIPMT 2007]
I

(A) CH 3 CH2 CH CH2 Cl

(C)

CH 3 CH CH2 CH2 I
Cl

30. CH 3 CH CH = CH 2 + HBr
CH 3

(B) CH 3CH2 C CH 3
Cl
I
(D) CH 2 CH 2 CH 2 C H
Cl
'A' ,

A (predominantly) is:

[AIPMT 2008]

(A) CH 3 CH CH CH 3
Br CH 3

(B)

CH 3 CH CH CH 3
CH 3 Br

Br
(C) CH 3 CH CH 2 CH2 Br (D) CH 3 C CH 2 CH 3
CH 3
CH 3

31. The order of reactivity of the alkenes,


(CH 3 )2 C = CH 2 ,
I

CH3 CH = CH2 ,
II

H 2 C = CH 2
III

when subjected to acid catalyzed hydration is:


[AMU (Med.) 2009, 10]
(A) I > II > III (B) I > III > II (C) III > II > I (D) II > I > III
32. Identify the product in the reaction
PhC

CMe

H 3O+ , Hg 2 +

[DUMET 2010]

(A) PhCH2 CH 2 CHO

(B) PhCOCH2 CH3

(C) PhCH 2 COCH3

(D) PhCOCOMe

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33. Reaction of HBr with propene in absence of peroxide is a/an:
[PMT (Kerala) 2011]
(A) electrophilic addition

(B) electrophilic substitution

(C) nucleophilic addition

(D) nucleophilic substitution

34. In the following reaction


CH 3
CH 3 C CH = CH 2
C2H 5

H 2O / H

(A)
major
product

The major product is :

+ (B)
minor
product

[AIPMT (Prelims) 2012]

CH 3
(A) H3 C C CH CH 3
CH 3 OH

(B) H3 C C CH CH 3
OH CH3

CH 3
(C) CH 2 C CH 2 CH 3
OH CH 3

CH 3
(D) H3 C C CH 2 CH 2
OH
CH 3

CH 3

35. In the reaction with HCl, an alkene reacts in accordance


with the Markovnikovs rule, to give a product 1-chloro-1methylcyclohexane. The possible alkene is : [AIPMT 2015]
CH 2

(A)

CH3

(B)

(A)

(B)
CH 3

(C) (A) and (B)

(D)

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Answers
01
Subjective Approach

1. Organic rea ctions are generally of 4 types.

(A) Substitution reaction Here old sigma bonds are broken


& new bond is formed.
A B C
A C B

(B) Addition reaction Here generally bonds are broken &


corresponding bonds are formed.
A=
B +C D

A B

C D

(C) Elimination reaction Here generally old bonds are


broken & corresponding a new bonds are formed.
A B

A=
B+C D

(D) Rearrangement reaction Here generally there is change


in connectivity of atom.
A B C
A C B

2. Rea gents are the a ttacking species which attacks over the
substrate. They may be e rich, e deficient or odd e species.

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3. Electrophiles are e deficient attacking species. They have e


deficiency in the form of either
(A) Positive charge

(B) Incomplete octet or

(D) Vacant orbital


Those factors which withdraws e density from electrophile
increases its electrophilicity.
4. Nucleophiles are e rich attacking species which a ttacks are
non-metal. They have complete octet with either presence of
lone pair or ve charge. Those factors which donates e density
towa rds nucle ophilic centre genera lly increa ses its
nucleophilicity.
5. Free radicals are odd e reactive species which attacks over
another free radicals or neutra l molecules. Free ra dicals are
generally formed by either presence of light, peroxide or high
temperature.
6. Leaving groups are those atoms or groups which goes out from
substrate from any chemical reaction. Those factors which
stabilizes leaving group increa ses its leaving group tendency.
O

7.

OH > PhO > CH 3 CO > CH 3 SO


O

I > Br > Cl > F

NH 3 H 2 O
O

8.

CH 3 SO > CH3 CO > PhO > HO


O
I > Br > Cl > F

H 2 O NH 3

9. Solvents a re the medium in which chemical reaction has to


take place. They are of 2 types
(A) Polar

(B) Non polar

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Polar solvents are those which have polarity in the molecule
such as H2 O, CH3 OH etc. Non polar solvent are those which
do not have any pola rity in molecule such a s benzene,
cyclohexane.
Polar solvent are further of 2 types
(A) Polar protic where H+ can be removed from solvent such
as H2 O, NH3 , CH3 COOH
(B) Polar aprotic where solvent do not ea sily loose H+ but
have polarity such as CH3 COCH3 , CH3 SCH3 etc.
10. Ba se a re those e rich species which a tta cks over H + .
Nucleophile are those e rich species which attacks over nonmainly C. Ligand are those e rich species which attacks over
metal.
11. General chemical reaction of alkene & alkynes are electrophilic
addition reaction.
E
CH 3 CH = CH2 ENu

CH3 CH CH 2

Nu
12. When unsymmetrica l a lkene or a lkyne rea cts with
unsymmetrical reagent in electrophilic addition reaction, then
positive part of reagent attached to that carbon which have
more number of hydrogen while negative part of reagent
attached to that carbon which have less number of hydrogen.
This rule is called as Markownikoff rule.
E
CH 3 CH = CH2

ENu

CH3 CH CH 2

Nu
13. Basic concept behind Markownikoff rule is the sta bility of
carbocation.
HCl
CCl 3 CH = CH2
CCl 3 CH 2 CH 2 Cl
(Violation of Markownikoff rule)
Cl
|

HCl
CH3 CH = CH 2
CH 3 CH CH 3

(Follow Markownikoff rule)

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14. (A) Bromine water test

(B) Baeyers reagent.

15. Dilute alkaline KMnO 4 is commonly called as Baeyers reagent.


It is used to distinguish sa tura tion & unsa tura tion of
carbon-carbon bond.
16. Addition of water to alkene is hydration reaction. Hydration
of a lkene ta kes pla ce in a cedic medium & rea ction &
mechanism follow as below. Reaction:
H2 O/H+

OH
|

CH 3 - CH = CH2 CH 3 CH- CH 3

Mechanism:

CH 3 CH = CH2

H+

..

CH3 CH CH 3

H 2O
H+

OH
CH3 CH CH 3

17. (A) Hydration in acidic medium using H 2 O /H + .


(B) Hydrobora tion-oxida tion using B 2 H6 followed by
H 2 O2 /OH .

(C) Oximercuration-demercuration using (Ac2 O)2 Hg / H 2 O


followed by NaBH 4 .
18. Oximercuration-demercuration is addition of water to alkene
using (Ac2 O)2 Hg / H 2 O followed by NaBH 4 .
OH
|

i) Hg (OAC)2 /H2O

CH3 CH = CH 2
CH3 CH CH3
ii) NaBH 4

19. Alkoxymercura tion-demercuration is addition of a lcohol


using (Ac2 O)2 Hg / ROH followed by NaBH 4 .
OR
i)(AC2 O)Hg/ROH

CH3 CH = CH 2
CH 3 CH CH 3
ii) NaBH 4

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20. Hydroboration-oxidation is a ddition of water using B 2 H6
followed by H 2 O2 /OH .
i)B H
ii) H2 O 2 /OH

2 6
CH3 CH = CH 2

- CH 3 CH 2 CH 2 OH

21. Hydroboration-oxidation is simply a ddition of wa ter but


machanism follow via 4 membered cyclic TS.
i) B H or BH

2 6
3
CH3 CH = CH 2

CH 3 CH2 CH 2 OH

ii) H2 O 2 /OH

Mechanism:
CH3 CH= CH 2
H BH2

CH 3 CH
H

CH 2

CH 3 CH 2 CH 2 BH2

BH 2 (CH 3 CH 2 CH 2 )3 B

H O /OH

2 2
(CH 3 CH 2 CH2 )3 B
3 CH 3 CH2 CH 2 OH

As here hydrogen attached as hydride so reaction follows


Markownikoff rule but product resembles Anti Markownikoff
product.
22. Bromination of alkene is simply the addition of bromine to
alkene to form dibromoalkane as product.
Reaction:
Br
Br2

CH 3 CH = CH2 CH 3 CH CH 2
|

Br

Mechanism:

CH 3CH= CH 2
Br
Br

72

Br
CH 3CH
CH 2
Br

Br
CH 3 CHCH 2

(Cyclic bromonium ion)

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Br

Alkene & Alkyne


23.

Br
Br2 /CCl 4

CH 3 CHCH 2
Br

Br
CH 3 CH=CH2

Br2 /H 2O

CH 3 CHCH 2 + CH3 CHCH 2


Br

Br
Br2 /NaCl

Cl Br

CH 3 CHCH 2 + CH3 CH CH2


Br

Br
Br2 /CH 3OH

OH

OCH 3

Br

CH 3 CHCH 2 + CH3 CHCH 2


Br

Br

24. Reaction:
Br
|

HBr
CH 3 CH = CH2
CH 3 CH CH 3

Mechanism:
Br
CH 3 CH = CH2

CH3 CH CH 3

Br

CH 3 CH CH 3

25. Reaction:
OH
|

HOCl

CH3 CH = CH 2
CH 3 CH CH 2
|

Cl

Mechanism:

CH 3CH=CH
.. Cl

OH

HO
CH 3 CH

CH 2

CH 3 CHCH2

Cl

Cl

OH

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26. Reaction:
Cl
|

ICl
CH3 CH = CH 2
CH 3 CH CH 2
|

Mechanism:
Cl
CH 3CH=CH 2
.. I

Cl

CH3CH

CH 2

CH 3 CHCH2
I

Cl

27.

Cl
OH
8

I
Cl
7
Br

Cl
1

HCl
ICl

HOCl
H2 O/H+

Br2 / H2O

OH
6
Br2 /CCl4

OH
2

ii) (Ac2 O)Hg/H2O


ii) NaBH4
i ) BH 3
ii) H 2O 2 /OH

Br
Br
5

OH

OH
3

28. When unsymmetrical alkene is treated with HBr in presence of


peroxide then hydrogen will attached to that carbon which
have less number of hydrogen while bromine is attached to
that carbon which have more number of hydrogen. This
concept is a gainst Ma rkownikoff rule so it is ca lled a s
Anti-Markownikoff rule. This abnormality was first reported
by kharasch so it is called as Kharasch effect.
HBr/(Ph C O)2 O

2
CH3 CH=CH 2
CH 3 CH2 CH2 Br

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29. NBS is N-Bromo Succinimide. NBS is used to replace benzylic
or allylic H with Br via free radical mechanism.
Br
|

NBS
CH 3 CH = CH2
CH 2 CH = CH 2

30. NCS is N-Chloro Succinimide. NCS is used to replace benzylic


or allylic H with Cl via free radical mechanism.
Cl
NCS

CH3 CH = CH 2
CH 2 CH = CH2

Cl
Cl 2

31. CH2 CH = CH 2
CH 2 CH = CH 2
High T

32. (A)

Br

Br

(B)
Br

(C)

(D)

Br

33. Reaction:
Cl
|

HCl
CH3 C CH
CH 3 C CH 3
|

Cl

Mechanism:
Cl
CH 3C CH

HCl

CH 3 C=CH 2

Cl

CH 3 C= CH 2

Cl
CH 3 CCH 3

Cl
Cl

CH3 CCH 3

Cl

34. Reaction:
O
CH 3 C

CH

HOCl

CH3 C CHCl 2

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Mechanism:.
OH
CH 3 C CH

OH

CH3 C=CH

.Cl

CH 3 C = CH

Cl

.Cl

OH

Cl

OH
HO

OH

O
CH 3CCHCl 2

H2 O

CH 3CCHCl 2

OH

CH 3 C

CHCl
Cl

OH

35. CH 3 C CH

i) B2H 6

ii) H 2O 2/OH

CH 3 CH2 C H

36. General hydration of alkyne occur in presence of HgSO4 of


along with dil H 2 SO 4 .
CH 3C CH

H 2O/HgSO 4 /H +

O
CH3 C CH3

Mechanism:

..

H 2O
CH 3 C CH

Hg 2+

OH

CH 3C=CH

H +

CH 3C=CH2

O
CH 3C CH3

Hg

37. Mercury sulpha te rea cts with a lkyne a nd form a n


intermediate over which water attacks to form product.

..

H 2O
CH 3C

CH

HgSO 4

CH 3C=CH

OH
CH 3C=CH 2

Hg
Intermediate

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O
CH 3CCH 3

Alkene & Alkyne


Cl

38.

HCl

39.

HCl

Cl

40. Intermediates formed from alkene is generally more stable than


intermediate formed from alkyne. So alkenes are more reactive
than alkynes.
+
CH 3CH=CH 2 E

CH3 CHCH 2
E
(more stable)

CH 3C

E+

CH

CH 3C=CH
E
(less stable)

41. As alkene, Alkynes & water are electron rich so H+ is added to


create electron deficient centre in alkene or alkyne over which
water will attack.
CH 3CH

CH2

H+

CH 3CHCH 3

+
CH 3C CH H CH 3C=CH 2

CH3

CH3

42. CH3 CH CH2 CH 2 OH


X
CH 3 OH
|

43. CH3 CH CH CH 3
X

CH3 CH CH2 C H
Y

CH3
|

CH 3 CH C CH 3

O
Y

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Br

44.

Br
M

Br
Br

Br
Br

Br

Br
+

Br

Br
O

Br

Br

Br

OCH3

Br

Br

Br

OCH 3
O

Br

Br

Cl

Br

Br

Br

Br

Cl
P

Br

Br

Cl

Br
1

Cl
8

HCl

O
O2
H
g/
)H BH 4
Br2
O
a
c2
A ii) N
(
i)

i) B 2H 6
ii) CH 3COOH
O

45.

O
6

i) B 2H 6
ii) H 2O 2 /OH
+

H 2O/H /Hg

ICl

Cl

78

Br

Cl

Cl

I
I

Cl
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3
2+

Alkene & Alkyne


46. Terminal alkyne have acidic hydrogen so give white ppt with
Tollens rea gent & red ppt with Cu 2 Cl 2 /NH 4 OH but
non-terminal alkyne do not give such reactions.
Tollen's reagent

RC C Ag
white ppt

RC CH
Cu2 Cl 2 / NH 4OH

RC C Cu
Red ppt

Tollen's reagent

No ppt

RC CR
Cu 2Cl 2 /NH 4OH

No ppt

47.
48. Rate of electrophilic addition reaction depends on the stability
of carboca tion formed after protonation while stability of
substrate depends on electronic delocalization of bond.
49. Rate of electrophilic addition reaction depends on stability of
carbocation. Carbocation formed by 1,3 -Butadiene is more
stable than carbocation formed by But-1-ene so is the order.
Br

50.

Br

HBr

Br

51.

+
Br

(B)
Br

O
53. (A) CH CCH
3
3

Br

Br

HBr

52. (A)

Br

Br

Br

(C)
O

(B)

Br
O (D)

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O

(C)

(D)

OH

OH + HC

..OH
54. PhCHC CH

..

H 2O

PhCHC CH

PhCH=C=CH H+
OH

PhCH=C=CH

PhCH=CHCH

55. (A)

HO

(B)
OH

(C)

(D)

Ph
Ph

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Answers
02
Objective Approach

01.

(B)

02.

(B)

03.

(B)

04.

(A)

05.

(A)

06.

(B)

07.

(A)

08.

(C)

09.

(A)

10.

(B)

11.

(B)

12.

(C)

13.

(A)

14.

(D)

15.

(B)

16.

(B)

17.

(B)

18.

(D)

19.

(D)

20.

(B)

21.

(D)

22.

(B)

23.

(B)

24.

(C)

25.

(B)

26.

(C)

27.

(C)

28.

(B)

29.

(D)

30.

(C)

31.

(D)

32.

(B)

33.

(B)

34.

(D)

35.

(C)

36.

(B)

37.

(D)

38.

(A)

39.

(A)

40.

(D)

41.

(A)

42.

(B)

43.

(C)

44.

(A)

45.

(C)

46.

(B)

47.

(B)

48.

(C)

49.

(B)

50.

(A)

51.

(B)

52.

(D)

53.

(A)

54.

(B)

55.

(B)

56.

(B)

57.

(D)

58.

(B)

59.

(B)

60.

(B)

61.

(A)

62.

(B)

63.

(A)

64.

(A)

65.

(C)

66.

(D)

67.

(A)

68.

(B)

69.

(A)

70.

(A)

71.

(C)

72.

(A)

73.

(A)

74.

(D)

75.

(A)

76.

(B)

77.

(A)

78.

(D)

79.

(A)

80.

(D)

81.

(C)

82.

(C)

83.

(D)

84.

(B)

85.

(A)

86.

(A)

87.

(B)

88.

(C)

89.

(C)

90.

(C)

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91.

(C)

92.

(C)

93.

(C)

94.

(A)

95.

(C)

96.

(B)

97.

(B)

98.

(D)

99.

(C)

100.

(B)

101. (C)

102. (A)

103. (A)

104. (B)

105.

(C)

106. (C)

107. (C)

108. (B)

109. (B)

110.

(C)

111. (A)

112. (C)

113. (B)

114. (D)

115.

(D)

116. (A)

117. (B)

118. (D)

119. (A)

120.

(A)

121. (B,C)

122. (A,B,C,D) 123. (A,B,D)

124.(B,D)

125. (A,C,D)

126. (B,C)

127. (A,B,C)

128.(A,C,D)

129. (C,D)

130. (B,C,D)

131. (A,B,C,D) 132.(A,B,C)

133. (B,C)

134. (A,B,C)

135. (A,B)

137. (A,B,C,D) 138. (A,C,D)

136.(A,B,C)

139. (A,B,C,D) 140.(A,C)

141. (B,D)

142. (A,B,C,D) 143. (A,B,C,D) 144.(A,B,D)

145. (A,B,C)

146. (A,B)

149. (C,D)

150. (A,B)

147. (A,C)

148.(B,C)

151. (A)

152. (A)

153. (C)

154. (A)

155.

(B)

156. (B)

157. (C)

158. (A)

159. (A)

160.

(B)

161. (AP, BQ, CS, DT)

162. (AP, BR, CS, DQ)

163. (AQ, BP, CR, DS)

164. (AS, BR, CP,Q, DP,Q)

165. (AR, BP,Q, CP, DQ,R,S)


166. (B)

167. (A)

168. (A)

169. (C)

170.

(C)

171. (D)

172. (B)

173. (C)

174. (C)

175.

(B)

176. (4)

177. (3)

178. (1)

179. (4)

180.

(2)

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Answers
03
World of Competitions

01.

06.

(C)

(B)

02.

07.

(C)

(A)

03.

08.

(C)

(A)

04.

(D)

05.

OH

Q H

09.

(D)

10.

(A)

11.

(A)

12.

(B)

13.

P
(C)

15.

(D)

16.

(C)

17.

(D)

18.

(A)

19.

(C)

20.

(A)

21.

(C)

22.

(C)

23.

(A)

24.

(B)

25.

(A)

26.

(B)

27.

(A)

28.

(B)

29.

(B)

30.

(D)

31.

(C)

32.

(B)

33.

(A)

34.

(B)

35.

(C)

14.

(A)

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