Question

Draw the structure of the organic product(s) of the grignard reaction between dimethyl carbonate (ch3oco2ch3) and excess phenylmagnesium bromide, followed by aqueous workup.

Answer 1

When grignard reagent is used in excess then the intermediates formed will further react to give the corresponding product. This reaction will proceed until alcohol is produced.

In this reaction, in first step ester is formed, which further reduces to ketone and ketone further reacts with grignard reagent to produce tertiary alcohol. The reaction is shown below, with the products highlighted in RED.