Organic Chemistry : Organic Chemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

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Example Question #39 : Other Reactions

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What is the product of the given reaction?

Possible Answers:

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Correct answer:

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Explanation:

The reaction given involves the direct alkylation of a ketone containing compound by the production of an enolate ion. The alpha hydrogen to the ketone group which is weakly acidic can be deprotonated in the presence of a base. LDA is a mild base that converts these compounds to the enolate ion. On the last step, through nucleophilic substitution by reaction with an alkyl halide with the enolate ion yields an alkyl group in the alpha position. LDA is sterically hindered therefore allowing for the production of an enolate ion without nucleophlic addition. Similarly, an ester or nitrile containing compound can also undergo this type of reaction.

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