Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Identify the major product formed in the following reaction sequence:
Correct answer
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Step-by-step solution
The reaction sequence proceeds as follows: 1. Grignard Reaction: The starting material is methyl cyclohexanecarboxylate, an ester. When treated with excess phenylmagnesium bromide ( PhMgBr ), the Grignard reagent attacks the electrophilic carbonyl carbon. The first equivalent of PhMgBr substitutes the methoxy group ( -OMe ) to form a ketone, cyclohexyl phenyl ketone. A second equivalent of PhMgBr then attacks the ketone to form a tertiary alkoxide. Upon hydrolysis ( H ₂ O ), the alkoxide is protonated to yield the