The Addition of Either the Methyl Grignard Reagent or Methyllithium

question 2

Multiple Choice

The addition of either the methyl Grignard reagent or methyllithium to camphor,followed by hydrolysis,produces a tertiary alcohol known as 2-methylisoborneol,an algal metabolite which imparts a musty odor to water at very low concentrations.However,the yield of alcohol does not exceed 50%,and large amounts of camphor are recovered from the reaction even when a large excess of the Grignard or lithium reagent are used.What would be the most plausible explanation?

• A) Ketones do not react with Grignard or lithium reagents.
• B) The Grignard or lithium reagent had obviously degraded during storage.
• C) The mechanism requires that,for each alcohol formed,one ketone molecule must remain unreacted.
• D) With hindered ketones,the organometallic reagent could function as a base rather than as a nucleophile.
• E) Alcohol formed early in the reaction could form an unreactive hemiacetal with remaining ketone.

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