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A common illicit synthesis of methamphetamine involves an

Chapter 11, Problem 67SP

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QUESTION:

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring (Section 17-14C), but in this case it eliminates the hydroxyl group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.

\(\text { OH }\)

\(\mathrm{CH}_{3}\)

\(\mathrm{NHCH}_{3}\)

\(\frac{L i}{N H_{3}(l), E t O H}\)

Equation transcription:

Text transcription:

{ OH }

{CH}{3}

{NHCH}{3}

frac{L i}{N H{3}(l), E t O H}

Questions & Answers

QUESTION:

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring (Section 17-14C), but in this case it eliminates the hydroxyl group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.

\(\text { OH }\)

\(\mathrm{CH}_{3}\)

\(\mathrm{NHCH}_{3}\)

\(\frac{L i}{N H_{3}(l), E t O H}\)

Equation transcription:

Text transcription:

{ OH }

{CH}{3}

{NHCH}{3}

frac{L i}{N H{3}(l), E t O H}

ANSWER:

Solution:

Step 1

In this reaction a solution of ephedrine in alcohol is added to liquid ammonia, followed by lithium metal. This reaction mechanism is similar to that of  Birch reduction reaction, in which the reduction of aromatic ring usually carried out , but in this case it eliminates the hydroxyl group of ephedrine to form methamphetamine.

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