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.
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.
2. Replace the identified carboxyl with a hydrogen.
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