What is the possible product when CH_3MgBr (e | vedclass

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(C) When an ester $(RCOOR')$ reacts with an excess of Grignard reagent $(R''MgX)$,it first forms a ketone,which then reacts further with another molec

Vedclass · Accepted Answer

$2-$methylbutan$-2-$ol

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(C) When an ester $(RCOOR')$ reacts with an excess of Grignard reagent $(R''MgX)$,it first forms a ketone,which then reacts further with another molecule of the Grignard reagent to form a tertiary alcohol.For an ethyl ester $(RCOOCH_2CH_3)$,the reaction with excess $CH_3MgBr$ proceeds as follows:$1$. $RCOOCH_2CH_3 + CH_3MgBr \rightarrow RCOCH_3 + CH_3CH_2OMgBr$$2$. $RCOCH_3 + CH_3MgBr \rightarrow R-C(OH)(CH_3)_2$Assuming the ethyl ester is ethyl acetate $(CH_3COOCH_2CH_3)$:$CH_3COOCH_2CH_3 + 2CH_3MgBr \rightarrow CH_3-C(OH)(CH_3)_2 + CH_3CH_2OMgBr$The product is $2$-methylpropan-$2$-ol (tert-butyl alcohol).However,if the ester is ethyl propionate $(CH_3CH_2COOCH_2CH_3)$:$CH_3CH_2COOCH_2CH_3 + 2CH_3MgBr \rightarrow CH_3CH_2-C(OH)(CH_3)_2 + CH_3CH_2OMgBr$The product is $2$-methylbutan-$2$-ol.Given the options provided,option $C$ represents $2$-methylbutan-$2$-ol,which corresponds to the reaction of ethyl propionate with excess $CH_3MgBr$.

What is the possible product when $CH_3MgBr$ (excess) reacts with an ethyl ester?

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