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60
Subjective

Write following conversions

(i) Nitrobenzene $\longrightarrow$ Acetanilide

(ii) Acetanilide $\longrightarrow \mathrm{p}$-nitroaniline

Explanation

(i) Nitrobenzene can be converted into acetanilide as follows

(ii) Acetanilide can be converted into p-nitroaniline as follows

61
Subjective

A solution contains 1 g mol. each of p-toluene diazonium chloride and p -nitrophenyl diazonium chloride. To this 1 g mol. of alkaline solution of phenol is added. Predict the major product. Explain your answer.

Explanation

The above stated reaction is an example of electrophilic aromatic substitution. In alkaline medium, phenol generates phenoxide ion which is more electron rich than phenol and more reactive for electrophilic attack. The electrophile in this reaction is aryldiazonium cation. As we know, stronger the electrophile faster is the reaction. p-nitrophenyldiazonium cation is a stronger electrophile than $p$-toluene diazonium cation.

So, nitrophenyl diazonium chloride couples preferentially with phenol.

62
Subjective

How will you bring out the following conversion?

Explanation

Complete conversion of above reaction can be shown as

63
Subjective

How will you carry out the following conversion?

Explanation

Conversion of benzene to p-nitroaniline can be done as

64
Subjective

How will you carry out the following conversion?

Explanation

Conversion of aniline to m-bromo nitrobenzene can be completed as