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Chapter 20, Problem 29P

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QUESTION:

A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide.

Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction ( Section \(11.10\) ) , called a Cope elimination.

In this reaction, a tertiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base.

Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?

Equation Transcription:

Text Transcription:

11.10

Questions & Answers

QUESTION:

A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide.

Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction ( Section \(11.10\) ) , called a Cope elimination.

In this reaction, a tertiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base.

Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?

Equation Transcription:

Text Transcription:

11.10

ANSWER:

Solution 29P

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