Write a mechanism for the formation of triphenylmethanol from the reaction of phenylmagnesium bromide and diethyl carbonate..
1 answer:
The reaction proceeds through nucleophilic acyl substitution reaction.
Phenyl magnesium bromide substitutes one ethoxide ion in the nucleophilic acyl substitution reaction that drives the process forward. A subsequent equivalent of phenyl magnesium bromide produces triphenyl methanol through a nucleophilic addition reaction with the resultant keto group.
There are two ethoxy leaving groups in diethyl carbonate. Tertiary alcohol is created when diethyl carbonate combines with too much Grignard reagent. The Grignard reagent attacks the carbonyl carbon three times in the mechanism to produce the tertiary alcohol.
The mechanism is shown below:
Learn more about Grignard reagent here:
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