CH_3COOCH_2CH_3 + PhMgBr_{(excess)} to P xrig | vedclass

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(B) The starting material is ethyl acetate $(CH_3COOCH_2CH_3)$.When an ester reacts with an excess of a Grignard reagent $(PhMgBr)$,the first equivale

Vedclass · Accepted Answer

$Ph_2C(OH)CH_3$

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(B) The starting material is ethyl acetate $(CH_3COOCH_2CH_3)$.When an ester reacts with an excess of a Grignard reagent $(PhMgBr)$,the first equivalent of the Grignard reagent attacks the carbonyl carbon to form a ketone intermediate $(CH_3-CO-Ph)$ and an alkoxide $(CH_3CH_2O^-)$.The ketone intermediate is more reactive than the ester,so it immediately reacts with a second equivalent of $PhMgBr$ to form a tertiary alkoxide $(CH_3-C(Ph)_2-O^-)$.Upon hydrolysis with $H_2O$,the alkoxide is protonated to form the final tertiary alcohol product,$CH_3C(OH)(Ph)_2$.Comparing this with the options,the correct structure is $Ph_2C(OH)CH_3$.

$CH_3COOCH_2CH_3 + PhMgBr_{(excess)} \to P \xrightarrow{H_2O} Q$;
$Q$ is

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$CH_3COOCH_2CH_3 + PhMgBr_{(excess)} \to P \xrightarrow{H_2O} Q$;$Q$ is