Reactivity of 2-Butanone with Grignard Reagent

Very Hard Organic Chemistry Carbonyl Chemistry

Consider the reaction of 2-butanone, a simple ketone, with 1 equivalent of a Grignard reagent (ethylmagnesium bromide) followed by acidic work-up. This reaction involves the formation of a tertiary alcohol. However, when considering reactivity and potential side reactions, there are several mechanistic steps to analyze.

Which of the following statements about the product of this reaction is true?

The product will be optically active due to the presence of a chiral center.

The product contains no functional groups that would undergo further reaction with excess Grignard reagent.

The product will have a higher boiling point than the starting ketone due to increased hydrogen bonding.

The product will form a stable hemiacetal under acidic conditions after reaction with water.

Hint

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