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Question

Which of these will produce the highest yield in Friedel Craft reaction ?

A
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B
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C
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D
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Solution

The correct option is D
A Friedel-Crafts reaction is an organic coupling reaction involving an electrophilic aromatic substitution that is used for the attachment of substituents to aromatic rings. The two primary types of Friedel-Crafts reactions are the alkylation and acylation reactions. These reactions were developed in the year 1877 by the French chemist Charles Friedel and the American chemist James Crafts.

It can be noted that both these reactions involve the replacement of a hydrogen atom (initially attached to the aromatic ring) with an electrophile. Aluminium trichloride (AlCl3) is often used as a catalyst in Friedel-Crafts reactions since it acts as a Lewis acid and coordinates with the halogens, generating an electrophile in the process.

In option (a), here electron displacement is from ring to group due to −M effect of CONH2 group. Therefore ring is highly deactivated.

Both Phenol & Aniline do not undergo Friedel craft reaction as both of them will form the deactivated ring.

Electron displacement is from group to the ring due to +M effect of chlorine.

So most reactive among the given compounds for Friedel Craft reaction is chlorobenzene.

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