Carboxylic Acids - What Is Decarboxylation?

3 important questions on Carboxylic Acids - What Is Decarboxylation?

When is a carboxylic acid decarboxylated?

For most carboxylic acid only when heated to very high temperatures, except carboxylic acids with a carbonyl group on the β-carbon. These will decarboxylate under mild heating.

What are the steps in the decarboxylation mechanism of β-ketocarboxylic acid (3-oxocarboxylic acid)?

1. Rearrangement of bonds to give carbon dioxide and the enol of a ketone.
2. Keto-enol tautomerism to form the stable keto form.

How to predict the product of a β-decarboxylation reaction?

1. Identify the carboxyl that has a β-carbonyl.
2. Replace the identified carboxyl with a hydrogen.

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