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Chapter 22: 53E (page 752)

When an optically active carboxylic acid such as (R)-2-phenylpropanoic acid is brominated under Hell鈥揤olhard鈥揨elinskii conditions, is the product optically active or racemic? Explain.

Short Answer

Expert verified

The compound, (R)-2-phenylpropanoic acid is brominated under Hell鈥揤olhard鈥揨elinskii conditions produces racemic mixture.

Step by step solution

01

The overall reaction

The overall reaction involves the reaction between a carboxylic acid and Br2/PBr3 followed by hydrolysis. This forms an alpha bromo carboxylic acid.

The overall reaction

02

Mechanism of Hell-Volhard-Zelinskii reaction

The mechanism of Hell-Volhard-Zelinskii reaction with (R)-2-phenylpropanoic acid is as follows,

HVZ reaction

Bromination of (R)-2-phenylpropanoic acid produces racemic mixture of 2-bromo-2-phenylpropanoic acid.

Formation of racemic mixture

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Most popular questions from this chapter

Heating carvone with aqueous sulfuric acid converts it into carvacrol. Propose a mechanism for the isomerization.


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.

For each reaction below, give the corresponding keto/enol tautomer and provide the complete mechanism.

Show how you might prepare the following compounds using an alkylation reaction as the key step:

If methanol rather than water is added at the end of a Hell鈥揤olhard鈥揨elinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.
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