Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(d) ethyl acetate → 3-methylpentan-3-ol

검증된 단계별 안내

Identify the starting material (ethyl acetate) and the target product (3-methylpentan-3-ol). Ethyl acetate is an ester, and the target compound is a tertiary alcohol. This suggests that the synthesis will involve a Grignard reaction, as Grignard reagents are commonly used to form tertiary alcohols.

Prepare the Grignard reagent needed for the reaction. To form 3-methylpentan-3-ol, the Grignard reagent should be derived from 2-methylpropyl bromide (CH₃)₂CHCH₂Br. React this alkyl halide with magnesium (Mg) in dry ether to form the Grignard reagent (CH₃)₂CHCH₂MgBr.

React the Grignard reagent (CH₃)₂CHCH₂MgBr with ethyl acetate (CH₃COOCH₂CH₃). The Grignard reagent will attack the carbonyl carbon of the ester, leading to the formation of a ketone intermediate (3-methylpentan-2-one).

Add a second equivalent of the Grignard reagent (CH₃)₂CHCH₂MgBr to the ketone intermediate (3-methylpentan-2-one). This will result in the formation of a tertiary alcohol after the addition reaction.

Perform an acidic workup (e.g., using H₃O⁺) to protonate the alkoxide intermediate and obtain the final product, 3-methylpentan-3-ol.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the synthesis of 3-methylpentan-3-ol from ethyl acetate, understanding how nucleophiles can displace groups is crucial for planning the reaction steps.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles, allowing for the formation of carbon-carbon bonds. In this synthesis, a Grignard reagent can be used to add a carbon chain to the carbonyl carbon of an intermediate, facilitating the conversion of ethyl acetate to the desired alcohol.

Functional Group Interconversion

Functional group interconversion refers to the transformation of one functional group into another, which is often necessary in multi-step syntheses. In the conversion of ethyl acetate to 3-methylpentan-3-ol, it is essential to understand how to manipulate functional groups, such as converting esters to alcohols, to achieve the final product.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.(d) ethyl acetate → 3-methylpentan-3-ol