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Chapter 17: 74P (page 845)

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, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Short Answer

Expert verified

Usually, the Birch reduction is used to convert arenes to cyclohexadiene but in this, in the presence of liquid ammonia and lithium metal and alcohol, it eliminates the hydroxyl group present.

Step by step solution

01

Birch Reduction

Usually, the Birch reduction is used to convert arenes to cyclohexadiene but in this, in the presence of liquid ammonia and lithium metal and alcohol, it eliminates the hydroxyl group present.

02

Mechanism of the reaction

The ephedrine is treated with lithium metal and replaces hydrogen with Li which reacts with a proton to form the carbocation and then a radical. This radical on the addition of electron form a carbanion which reacts with ethyl alcohol to form the methamphetamine as the desired product.

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Most popular questions from this chapter

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)

Predict the site(s) of electrophilic attack on these compounds.

(a)

(b)

What products would you expect from the following coupling reactions?

(a)

(b)

(c)

(d)

(e)

1,4-Benzoquinone is a good Diels鈥揂lder dienophile. Predict the products of its reaction with

(a) buta-1,3-diene

(b) cyclopenta-1,3-diene

Unlike most other electrophilic aromatic substitutions, sulfonation is often reversible. When one sample of toluene is sulfonated at 0 掳C and another sample is sulfonated at 100 掳C, the following ratios of substitution products result:

(a) Explain the change in the product ratios when the temperature is increased.

(b) Predict what will happen when the product mixture from the reaction at 0 掳C is heated to 100 掳C.

(c) Because the SO3Hgroup can be added to a benzene ring and removed later, it is sometimes called a blocking group. Show how 2,6-dibromotoluene can be made from toluene using sulfonation and desulfonation as intermediate steps in the synthesis
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