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Chapter 17: 52P (page 847)

Which of the following compounds decarboxylates when heated?

Short Answer

Expert verified

On heating, carboxylic acid releases carbon dioxide gas. After releasing carbon dioxide, the remaining product should be stable.[l1]

Compound C is a β ketone. Hence, the remaining electron can be delocalized by the keto group as shown below.

[l1]Nothing about delocalization of electrons mentioned here.

Step by step solution

01

Delocalization of electrons in (c)

On heating, carboxylic acid releases carbon dioxide gas. After releasing carbon dioxide, the remaining product should be stable.[l1]

Compound C is a β ketone. Hence, the remaining electron can be delocalized by the keto group as shown below.

[l1]Nothing about delocalization of electrons mentioned here.

02

A and B do not have β carboxylic group

Compounds A and B don't decarboxylate on heating because they don't have βcarboxylic group to stabilize the negative charge on the ring by the loss of carbon dioxide.

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Most popular questions from this chapter

How could each of the following compounds be prepared from a ketone and an organohalide?

a.

b.

An α,β-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation–oxidation reaction. A selenoxide is formed as an intermediate. Propose a mechanism for the reaction.

a. If the biosynthesis of palmitic acid were carried out with CD3COSR and nondeuterated malonyl thioester, how many deuterium atoms would be incorporated into palmitic acid?

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Use retrosynthetic analysis to plan a synthesis of the following target molecules. The only carbon-containing compounds available for the syntheses are cyclohexanol, ethanol, and carbon dioxide.

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Explain why a racemic mixture is formed when (R)-2-methylpentanal is dissolved in an acidic or basic solution.
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