Predict the major product for the following reaction.

Question

Quizplus · Accepted Answer

The reaction involves a Grignard reagent reacting with an ester. The Grignard reagent will act as a nucleophile, attacking the carbonyl carbon of the ester. The resulting intermediate will undergo protonation to yield the final product. In this case, the Grignard reagent is an alkyl magnesium bromide, CH3CH2MgBr. When it attacks the ester, it will displace the leaving group (in this case, the ethoxy group) and form a new bond with the carbonyl carbon. This results in the formation of an alkoxide intermediate. Protonation of the alkoxide intermediate will yield the final product. The product formed will be a tertiary alcohol, III, because the carbonyl carbon in the ester is attached to two alkyl groups and one hydrogen atom, and the Grignard reagent adds another alkyl group, resulting in the formation of a tertiary alcohol. None of the other products have this arrangement of alkyl groups on the alcohol carbon.

Predict the Major Product for the Following Reaction