Chapter 22

Haloalkanes and Haloarenes

Only One Option Correct Type Questions

1. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT-JEE-2007 (Paper-2)]

(A) 1 (B) 2
(C) 3 (D) 4

2. The major product of the following reaction is [IIT-JEE-2008 (Paper-1)]

Me Br

F – +
PhS Na
dimethylformamide

NO2

Me SPh SPh
Me

F F
(A) (B)

NO2 NO2

Me Br Me SPh

SPh SPh
(C) (D)

NO2 NO2

3. KI in acetone, undergoes SN2 reaction with each of P, Q, R and S. The rates of the reaction vary as
[JEE (Adv)-2013 (Paper-1)]
O
Cl
H3 C – Cl Cl Cl

P Q R S

(A) P > Q > R > S (B) S > P > R > Q

(C) P > R > Q > S (D) R > P > S > Q
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One or More Option(s) Correct Type Questions

4. The correct statement(s) about the compound given below is (are) [IIT-JEE-2008 (Paper-1)]

Cl H
CH3
H 3C
Cl H
(A) The compound is optically active
(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
5. The correct statement(s) about the compound H3C(HO)HC—CH=CH—CH(OH)CH3 (X) is are
[IIT-JEE-2009 (Paper-1)]
(A) The total number of stereoisomers possible for X is 6
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2
6. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct?
[IIT-JEE-2012 (Paper-2)]
Cl
HO H HO H
H Cl
Cl CH 3
HO H H OH HO H

CH3 Cl CH3
M N O

CH3 CH3

H OH HO H

HO H HO H

Cl Cl
P Q
(A) M and N are non-mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical

7. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are)

[JEE (Adv)-2015 (Paper-1)]

H Br H Br
(A) (B) CH3
H 3C CH3 H 2C

H Br
H2C Br H
(C) CH3 (D)
H2C CH3
CH3

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8. For the following compounds, the correct statement(s) with respect to nucleophilic substitution reaction is(are)
[JEE (Adv)-2017 (Paper-2)]
Br Br

I II

CH3 CH3

H3C – C – Br Br
CH3
III IV
(A) I and III follow SN1 mechanism
(B) Compound IV undergoes inversion of configuration
(C) The order of reactivity for I, III and IV is : IV > I > III
(D) I and II follow SN2 mechanism
9. Which of the following plots is(are) correct for the given reaction?
CH3 CH3
([P]0 is the initial concentration of P) H 3C Br + NaOH H3 C OH + NaBr
CH3 CH3
P Q
[JEE (Adv)-2020 (Paper-2)]
Initial rate

t1/2
(A) (B)

[P]0
[P]0

[Q]  [P] 
ln  
(C) [P]0 (D)  [P]0 

time time
10. The reaction of Q with PhSNa yields an organic compound (major product) that gives positive Carius test on
treatment with Na2O2 followed by addition of BaCl2. The correct option(s) for Q is(are)
[JEE (Adv)-2021 (Paper-1)]

O2N

(A) O2N F (B) I

NO 2 O 2N

MeS

(C) Br (D) O2N

Cl

O2N MeS

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Matrix-Match / Matrix Based Type Questions

11. LIST-I contains reactions and LIST-II contains major products. [JEE (Adv)-2018 (Paper-2)]
List-I List-II

P. + 1.
ONa Br OH

Q. + HBr 2.
OMe Br

R. + NaOMe 3.
Br OMe

S. + MeBr 4.
ONa
O
5.

Match each reaction in LIST-I with one or more products in LIST-II and choose the correct option.
(A) P  1,5; Q  2; R  3; S  4 (B) P  1,4; Q  2; R  4; S  3
(C) P  1,4; Q  1,2; R  3,4; S  4 (D) P  4,5; Q  4; R  4; S  3,4

Integer / Numerical Value Type Questions

12. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic
KOH is [IIT-JEE-2011 (Paper-1)]

13. The maximum number of isomers (including stereoisomers) that are possible monochlorination of the following
compound, is [IIT-JEE-2011 (Paper-2)]
CH3
C
CH3CH2 CH2CH3
H
14. The total number(s) of stable conformers with non-zero dipole moment for the following compound is (are)
[JEE (Adv)-2014 (Paper-1)]
Cl
Br CH3
Br Cl
CH3
15. The total number of stereoisomers that can exist for M is [JEE (Adv)-2015 (Paper-1)]
H3C CH3

H3C

O
M
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16. In the following monobromination reaction, the number of possible chiral products is [JEE (Adv)-2016 (Paper-1)]

CH2CH2CH3
H Br Br2 (1.0 mole)

CH3 300 ºC
(1.0 mole)
(enantiomerically pure)

17. For the given compound X, the total number of optically active stereoisomers is _________.
[JEE (Adv)-2018 (Paper-2)]

HO HO

HO HO
X

This type of bond indicates that the configuration at the

specific carbon and the geometry of the double bond is fixed
This type of bond indicates that the configuration at the
specific carbon and the geometry of the double bond is NOT fixed

18. The maximum number of possible isomers (including stereoisomers) which may be formed on mono-
bromination of 1-methylcyclohex-1-ene using Br2 and UV light is ______. [JEE (Adv)-2021 (Paper-1)]
19. The number of isomeric tetraenes (NOT containing sp-hybridized carbon atoms) that can be formed from the
following reaction sequence is ________. [JEE (Adv)-2022 (Paper-2)]

20. The total number of chiral molecules formed from one molecule of P on complete ozonolysis (O3, Zn/H2O) is
________. [JEE (Adv)-2022 (Paper-2)]

  

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