Haloalkanes and Haloarenes · Chemistry · COMEDK

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MCQ (Single Correct Answer)

1

With reference to the two statements Assertion and Reason, choose the correct option.

Assertion: The order of reactivity towards $\mathrm{S}_{\mathrm{N}} 1$ reaction is: $\mathrm{C}_6 \mathrm{H}_5-\mathrm{CH}_2 \mathrm{Br}>\left(\mathrm{CH}_3\right)_3-\mathrm{C}-\mathrm{Br}>\left(\mathrm{CH}_3\right)_2-\mathrm{CH}-\mathrm{Br}$.

Reason: Among the given 3 compounds, the Benzyl carbocation formed is the most stable while Isopropyl carbocation is the least stable one.

COMEDK 2026 Afternoon Shift
2

Identify the wrong statement from the following

COMEDK 2026 Morning Shift
3

Select the reagents needed to convert Benzene to 4-Bromophenylpropene in the correct sequential order.

(A). $\mathrm{Cl}_2 / \Delta$

(B). $\left(\mathrm{CH}_3\right)_2-\mathrm{CHCl}$ /anhyd. $\mathrm{AlCl}_3$

(C). Alc. KOH

(D). $\mathrm{Br}_2 / \mathrm{Fe}$

COMEDK 2026 Morning Shift
4

Two statements, Assertion and Reason are given. With reference to them, choose the correct option.

Assertion: Hydrolysis of 2-Bromo-2-methylpropane follows $S_N 1$ mechanism which involves 2 steps and the first step is:

COMEDK 2026 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 2 English

Reason: The energy required to cleave $\mathrm{C}-\mathrm{Br}$ is taken from the energy released due to Inductive effect and hyper-conjugative effect.

COMEDK 2026 Morning Shift
5
The correct order of reactivity of halogens with alkanes is :
COMEDK 2025 Evening Shift
6
Choose the incorrect statement from the following.
COMEDK 2025 Afternoon Shift
7
Identify the incorrect statement.
COMEDK 2025 Afternoon Shift
8
Toluene when reacted with $\mathrm{Cl}_2$ gas at 385 K forms a product X which undergoes further reaction with Sodium ethoxide to yield product Y . The structure of Y is ___________ .
COMEDK 2025 Afternoon Shift
9

Identify the reagents to be used to complete the given reaction.

COMEDK 2025 Afternoon Shift Chemistry - Haloalkanes and Haloarenes Question 6 English

COMEDK 2025 Afternoon Shift
10

Identify the final product $[Z]$ formed when Chlorobenzene undergoes the given series of reactions:

COMEDK 2025 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 10 English

COMEDK 2025 Morning Shift
11
Which one of the following is a true statement with reference to reaction between 2- Bromo-2-methylpropane and aqueous KOH ?
COMEDK 2025 Morning Shift
12
Which of the following haloalkanes will give more than one isomeric product, on being heated with alc. KOH ?
COMEDK 2025 Morning Shift
13

Both reactions (i) and (ii) give the same compound X as the major product. Identify X

(i). 3-Methylbut-1-ene $+\mathrm{HCl} \rightarrow \mathrm{X}$

(ii). Neopentyl alcohol $+\mathrm{HCl}\left(\right.$ anh. $\left.\mathrm{ZnCl}_2\right) \rightarrow \mathrm{X}$

COMEDK 2025 Morning Shift
14

Identify the compound which gives an optically active haloalkane on reaction with $\mathrm{H}_2$ / Ni on heating.

A B C D
COMEDK 2025 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 11 English 1 COMEDK 2025 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 11 English 2 COMEDK 2025 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 11 English 3 COMEDK 2025 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 11 English 4

COMEDK 2025 Morning Shift
15

Identify the final product formed when Toluene undergoes a series of reactions with reagents given in the order:

(i) $$\mathrm{Cl}_2$$ / Sunlight

(ii) $$\mathrm{H}_2 \mathrm{O} / 373 \mathrm{~K}$$

(iii) Acetophenone / $$\mathrm{OH^-}$$ at $$293 \mathrm{~K}$$

COMEDK 2024 Evening Shift
16

Arrange the following compounds in the increasing order of their reactivity when each of them is reacted with chloroethane / anhydrous AlCl$$_3$$.

COMEDK 2024 Evening Shift Chemistry - Haloalkanes and Haloarenes Question 15 English

COMEDK 2024 Evening Shift
17

Match the names of reactions given in Column I with the appropriate reactions given in Column II.

No. Name of reaction No. Equations representing reactions
(A) Sandmeyer (P) $$
2 \mathrm{C}_6 \mathrm{H}_5 \mathrm{Cl}+\mathrm{Na} \text { (dry ether) } \rightarrow \text { Diphenyl. }
$$
(B) Fittig (Q) $$
\mathrm{CH}_3-\mathrm{CHBr}-\mathrm{CH}_3+\mathrm{AgF} \rightarrow \mathrm{CH}_3-\mathrm{CHF}-\mathrm{CH}_3+\mathrm{AgBr}
$$
(C) Swarts (R) $$
\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{Br}+\mathrm{Nal} \text { ( Acetone) } \rightarrow \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{I}+\mathrm{NaBr}
$$
(D) Finkelstein (S) $$
\mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}_2+\mathrm{Cl}-+\mathrm{Cu}_2 \mathrm{Br}_2 / \mathrm{HBr} \rightarrow \mathrm{C}_6 \mathrm{H}_5 \mathrm{Br}+\mathrm{N}_2
$$

COMEDK 2024 Evening Shift
18

Arrange the compounds $$\mathrm{A}, \mathrm{B}, \mathrm{C}$$ and $$\mathrm{D}$$ in the increasing order of their reactivity towards $$\mathrm{S_N}1$$ reaction.

$$ \begin{aligned} & \mathrm{A}=\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Cl} \\ & \mathrm{B}=\mathrm{C}_6 \mathrm{H}_5 \mathrm{Cl} \\ & \mathrm{C}=\mathrm{CH}_2=\mathrm{CH}-\mathrm{Cl} \\ & \mathrm{D}=\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{Cl} \end{aligned}$$

COMEDK 2024 Evening Shift
19

Identify the products C, D and F formed in the following sets of reactions.

COMEDK 2024 Evening Shift Chemistry - Haloalkanes and Haloarenes Question 16 English

COMEDK 2024 Evening Shift
20

Arrange the following compounds in the decreasing order of reactivity towards electrophilic substitution reaction.

(I) Chlorobenzene

(II) Nitrobenzene

(III) Benzene

(IV) Isopropylbenzene

COMEDK 2024 Afternoon Shift
21

Arrange the following in the order of increasing reactivity towards $$\mathrm{SN}_{\mathrm{2}}$$ reactions.

$$\begin{array}{ll} \left(\mathrm{CH}_3\right)_3 \mathrm{CCH}_2 \mathrm{Br}(\mathrm{P}) ; & \\\mathrm{CH}_3\left(\mathrm{CH}_2\right)_3 \mathrm{Br}(\mathrm{Q}) ; &\\ \mathrm{CH}_3 \mathrm{CH}_2-\mathrm{CH}\left(\mathrm{CH}_3\right)-\mathrm{CH}_2 \mathrm{Br}(\mathrm{R}) ; & \\\left(\mathrm{CH}_3\right)_2 \mathrm{CHCH}_2 \mathrm{CH}_2 \mathrm{Br}(\mathrm{S}) \end{array}$$

COMEDK 2024 Afternoon Shift
22

Choose the incorrect statement from the following.

COMEDK 2024 Afternoon Shift
23

Consider the following reaction

$$(\mathrm{CH}_3)_2 \mathrm{CHCH}_2 \mathrm{Br}+(\mathrm{CH}_3)_3 \mathrm{CCH}_2 \mathrm{Br} \xrightarrow[\Delta]{\mathrm{Na} \text { /dry ether }} \mathrm{X}+\mathrm{Y}+\mathrm{Z}$$

Identify the product which is not formed?

COMEDK 2024 Afternoon Shift
24

The major product obtained in the following reaction is :

COMEDK 2024 Afternoon Shift Chemistry - Haloalkanes and Haloarenes Question 20 English

COMEDK 2024 Afternoon Shift
25

Which one of the following compounds when reacted with $$\mathrm{NaOH}$$ (aq) undergoes Substitution Nucleophilic Bimolecular reaction with retention of configuration?

COMEDK 2024 Morning Shift
26

$$t$$-butyl chloride preferably undergo hydrolysis by

COMEDK 2023 Morning Shift
27

In Friedal-Crafts alkylation reaction of phenol with chloromethane, the product formed will be

COMEDK 2023 Morning Shift
28

COMEDK 2023 Morning Shift Chemistry - Haloalkanes and Haloarenes Question 31 English

Identify A, B and C.

COMEDK 2023 Morning Shift
29

Identify the compounds A, B, C and D.

$$ \text { 1,2,2,2-tetrachloroethane } \xrightarrow[\Delta]{\mathrm{Zn}}[\mathrm{A}] $$

[A] $$ \xrightarrow[675 \mathrm{~K}]{\text { Fe tube }} $$ [B] $$ \xrightarrow[\text { Conc. } \mathrm{H}_2 \mathrm{SO}_4]{\text { Conc. } \mathrm{HNO}_3} $$ [C] $$ \xrightarrow[\text { Anhydrous } \mathrm{AlCl}_3]{\mathrm{Cl} /}$$ [D]

COMEDK 2023 Evening Shift
30

The reactions taking place with $$\mathrm{2- Phenyl-2-bromopropane}$$ as the starting material is shown below. Identify [A] and [B] formed in the reaction.

$$ \mathrm{C}_6 \mathrm{H}_5-\mathrm{C}\left(\mathrm{CH}_3\right)_2^{-} \mathrm{Br} \xrightarrow[\Delta]{\text { KOH Alcoholic }}[\mathrm{A}] $$

$$ [\mathrm{A}]+\mathrm{HBr} \xrightarrow{\left(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CO})_2 \mathrm{O}\right.}[\mathrm{B}]$$

COMEDK 2023 Evening Shift
31

Which one of the following will undergo Nucleophilic substitution, by $$\mathrm{S}_{\mathrm{N}}{ }^1$$ mechanism, fastest?

COMEDK 2023 Evening Shift
32

Alkyl halides undergoing SN2 reaction do inverse

COMEDK 2022
33

The reaction $$\mathrm{ArN_2^ + C{l^ - }\buildrel {Cu/HCl} \over \longrightarrow ArCl + {N_2} + CuCl}$$ is called as

COMEDK 2021
34

Benzene reacts with chlorine in sunlight to give a final product

COMEDK 2020
35

An alkyl halide reacts with alcoholic ammonia in a sealed tube, the product formed will be

COMEDK 2020