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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

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.

Why do you suppose ketone halogenations in acidic media are referred to as being acid-catalyzed,whereas halogenations in basic media are base-promoted? In other words, why is a full equivalent of base required for halogenation?

Rank the following compounds in order of increasing acidity:

How would you synthesize the following compounds from cyclohexanone?

More than one step may be required.

Would you expect optically active (S)-3-methylcyclohexanone to be racemized on acid or base treatment in the same way as 2-methylcyclohexanone (Problem 22-51)? Explain.
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