One mole of the aldehyde ester shown is treated with a large excess of methylmagnesium bromide, followed by work-up. Assuming only nucleophilic additions and acyl substitution occur (no enolisation), how many moles of $CH X_{3} MgBr$ are consumed per mole of the compound? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

Methyl 4-oxobutanoate has an aldehyde and an ester. The aldehyde consumes 1 mol of Grignard reagent to give a secondary alkoxide. The ester consumes 2 mol: the first displaces methoxide to give a ketone, the second adds to that ketone to give a tertiary alkoxide. Total = 1 + 2 = 3.

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One mole of the aldehyde ester shown is treated with a large excess of methylmagnesium bromide, followed by work-up. Assuming only nucleophilic additions and acyl substitution occur (no enolisation), how many moles of CHX3​MgBr are consumed per mole of the compound? Give the answer as an integer.

Answer: 3

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