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Chapter 16: Q26E (page 524)

How would you synthesize the following compound starting from benzene? More than one step is needed.

Short Answer

Expert verified

It is the process of adding alkyl by replacing hydrogen in the aromatic ring. It is the electrophilic aromatic substitution reaction of the arene with the alkyl chloride.

Benzene first reacts with methyl chloride to form methylbenzene.

Step by step solution

01

Step-by-Step SolutionStep1:  Friedel craft alkylation

It is the process of adding alkyl by replacing hydrogen in the aromatic ring. It is the electrophilic aromatic substitution reaction of the arene with the alkyl chloride.

Benzene first reacts with methyl chloride to form methylbenzene.

02

 Nitration

Nitration occurs in the presence of nitrous acid with sulphuric acid which leads to direct substitution of the nitro group at the para position of 1-methyl benzene.

03

 Reaction with potassium permanganate

Potassium permanganate is a reagent used for the reduction of the methyl group to the carboxylic acid followed by hydrolysis.

04

 Formation of 4-nitrobenzoic acid

Steps followed in the formation of 4-nitrobenzoic aid are as follows:

  1. Friedel craft alkylation
  2. Nitration
  3. Reduction with potassium permanganate

Formation of 4-nitrobenzoic acid

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Most popular questions from this chapter

How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and para-substitution products can

be separated.

(a)o-Bromobenzoic acid (b)p-Methoxytoluene

(c)2,4,6-Trinitrobenzoic acid (d)m-Bromoaniline

Question: Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring has a large effect. Thepka of unsubstituted phenol, for example, is 9.89, while that of p-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.

At what position, and on what ring, would you expect the followingsubstances to undergo electrophilic substitution?

(a)

(b)

(c)

(d)

How would you prepare diphenylmethane, (Ph)2CH2 , from benzene and an acid chloride?

Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.
See all solutions

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