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Chapter 6: Problem 58

Which of the following sequence is best suited to convert benzene to 3 -chloro aniline? (a) nitration, reduction, chlorination (b) chlorination, nitration, reduction (c) nitration, chlorination, reduction (d) nitration, reduction, acetylation, chlorination, hydrolysis

Short Answer

Expert verified
A. Nitration, reduction, chlorination B. Chlorination, nitration, reduction C. Nitration, chlorination, reduction D. Nitration, reduction, acetylation, chlorination, hydrolysis Answer: B. Chlorination, nitration, reduction

Step by step solution

01

(Option A)

(a) nitration, reduction, chlorination: 1. Nitration: Benzene reacts with nitric acid (HNO₃) in the presence of a catalyst, typically sulfuric acid (H₂SO₄), to form nitrobenzene (C₆H₅NO₂). 2. Reduction: Nitrobenzene can be reduced to aniline (C₆H₇N) by treating it with a suitable reducing agent, such as hydrogen in the presence of a metal catalyst. 3. Chlorination: At this point, we have aniline and not 3-chloroaniline, so this sequence is not correct.
02

(Option B)

(b) chlorination, nitration, reduction: 1. Chlorination: Benzene reacts with chlorine gas (Cl2) in the presence of a catalyst, such as aluminum chloride (AlCl3) to give chlorobenzene (C6H5Cl). 2. Nitration: Chlorobenzene reacts with nitric acid (HNO3) in the presence of a catalyst, sulfuric acid (H2SO4) to form 3-nitrochlorobenzene (C6H4ClNO2). 3. Reduction: 3-nitrochlorobenzene can be reduced to 3-chloroaniline (C6H6ClN) by treating it with a suitable reducing agent, like hydrogen in the presence of a metal catalyst. This sequence of reactions does indeed produce the desired product, so option B is correct.
03

(Option C)

(c) nitration, chlorination, reduction: 1. Nitration: As in option A, benzene reacts with nitric acid to form nitrobenzene. 2. Chlorination: Nitrobenzene cannot be directly chlorinated at the desired position (meta-substituted), so this sequence is not correct.
04

(Option D)

(d) nitration, reduction, acetylation, chlorination, hydrolysis: 1. Nitration: As in option A, benzene reacts with nitric acid to form nitrobenzene. 2. Reduction: As in option A, nitrobenzene is reduced to aniline. 3. Acetylation: Aniline reacts with acetic anhydride ((CH₃CO)₂O) to form acetanilide (C₈H₉NO). 4. Chlorination: Acetanilide cannot be directly chlorinated at the desired position (meta-substituted), so this sequence is not correct. Based on the analysis of each option, the best-suited sequence to convert benzene to 3-chloroaniline is
05

Option B

chlorination, nitration, reduction.

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Most popular questions from this chapter

Identify the reactions in which both the nitrogen atoms of benzene diazonium chloride are retained in the product. (a) Reduction with zinc and hydrochloric acid (b) Reduction with \(\mathrm{SnCl}\), and hydrochloric acid (c) Reduction with sodium sulphite (d) Coupling reaction

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