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Chapter 22: Q28E (page 752)

Using curved arrows, propose a mechanism for the following reaction, one of the steps in the metabolism of the amino acid alanine.

Short Answer

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You need to propose a mechanism for the given reaction.

Step by step solution

01

Mechanism of the reaction

The mechanism of the given reaction using curved arrows is

02

Explanation of the mechanism

The starting material has one hydrogen on the carbon to the carboxylate ion. The abstraction of this proton shifts the electron flow towards the positively charged nitrogen. This helps the nitrogen to neutralize and gives the desired product.

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Most popular questions from this chapter

Although 2-substituted 2-cyclopentenones are in a base-catalyzed equilibrium with their 5-substituted 2-cyclopentenone isomers (Problem 22-55), the analogous isomerization is not observed for 2-substituted 2-cyclohexenones. Explain.

In the Hell–Volhard–Zelinskii reaction, only a catalytic amount of PBr3 is necessary because of the equilibrium below. Review the mechanism for the reaction of a carboxylic acid with thionyl chloride and propose a mechanism for the equilibrium.

Amino acids can also be prepared by a two-step sequence that involves Hell–Volhard–Zelinskii reaction of a carboxylic acid followed by treatment with ammonia. Show how you would prepare leucine, (CH3)2CHCH2CH(NH2)CO2H, and identify the mechanism of the second step.

How might you convert geraniol into either ethyl geranylacetate or geranylacetone?

Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case.

(a)Ethyl pentanoate (b)Ethyl 3-methylbutanoate

(c)Ethyl 2-methylbutanoate (d) Ethyl 2,2-dimethylpropanoate
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