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Question

How will you convert benzene into
(i) p-nitrobromobenzene

(ii) m-nitrochlorobenzene

(iii) p -nitrotoluene

(iv) acetophenone

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Solution

(i) Benzene can be converted into p-nitrobromobenzene as:
Electrophilic aromatic substitution of benzene with bromine in presence of ferric bromide gives bromobenzene. Nitration with conc. nitric acid and concentric sulphuric acid give a mixture of ortho-bromonitrobenzene and para-bromo nitrobenzene which are separated by fractional distillation.


(ii) Benzene can be converted into m-nitrochlorobenzene:
Nitration of benzene with conc nitric acid and conc sulphuric acid gives nitrobenzene. Chlorination with chlorine in presence of anhydrous aluminum chloride gives meta nitro chlorobenzene.

(iii) Benzene can be converted into p-nitrotoulene as:
Benzene reacts with methyl chloride in presence of anhydrous aluminum chloride to give toluene. After that, toulene reacts with a nitrating mixture to give a mixture of p-nitrotoluene and o-nitrotoluene. The mixture of p-nitrotoluene and o-nitrotoluene can be separated by fractional distillation.

(iv) Benzene can be converted into acetophenone as:
Friedel Craft's acylation of benzene with acetyl chloride in presence of anhydrous aluminum chloride gives acetophenone.




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