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Chapter 22: Q29E (page 752)

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

Short Answer

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Mechanism

Step by step solution

01

Mechanism of the reaction

The mechanism of the given reaction using curved arrows is

Mechanism

02

Explanation of the mechanism

The decarboxylation initiated by the electrons on the oxygen of the carboxylate ion forms the enolate. Then the enolate gets protonated and forms the desired product.

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Most popular questions from this chapter

When an optically active carboxylic acid such as (R)-2-phenylpropanoic acid is brominated under Hell–Volhard–Zelinskii conditions, is the product optically active or racemic? Explain.

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.

The two isomers cis- and trans-4-tert-butyl-2-methylcyclohexanone are interconverted by base treatment. Which isomer do you think is more stable, and why?


The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.

Draw structures for the enol tautomers of the following compounds:

(a) Cyclopentanone

(b) Methyl thioacetate

(c) Ethyl acetate

(d) Propanal

(e) Acetic acid

(f) Phenylacetone
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