Reaction of benzene with Me_{3}CCOCl in the p | vedclass

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Question

(B) The reaction of benzene with $Me_{3}CCOCl$ (pivaloyl chloride) in the presence of anhydrous $AlCl_{3}$ is a Friedel-Crafts acylation reaction. How

Vedclass · Accepted Answer

$Ph-CMe_{3}$

Vedclass · Answer

(B) The reaction of benzene with $Me_{3}CCOCl$ (pivaloyl chloride) in the presence of anhydrous $AlCl_{3}$ is a Friedel-Crafts acylation reaction. However, because the acyl group is bulky ($tert$-butyl group), the intermediate acylium ion is highly hindered. Under these conditions, the reaction often proceeds with decarbonylation, leading to the formation of $tert$-butylbenzene $(Ph-CMe_{3})$ as the major product. The reaction proceeds as follows: $C_{6}H_{6} + Me_{3}CCOCl \xrightarrow{Anhy. AlCl_{3}} C_{6}H_{5}COCMe_{3} + HCl$ $C_{6}H_{5}COCMe_{3} \xrightarrow{-CO} C_{6}H_{5}CMe_{3}$

Reaction of benzene with $Me_{3}CCOCl$ in the presence of anhydrous $AlCl_{3}$ gives:

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