-Imino carboxylic acids such as the one in Fig. P20.53 decarboxylate very rapidly provided that the pH...

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β-Imino carboxylic acids such as the one in Fig. P20.53 decarboxylate very rapidly provided that the pH is neither too low nor too high.

(a) Give a curved-arrow mechanism for the decarboxylation reaction shown in Fig. P20.53.

(b) Explain why very low or very high pH values reduce the rate of this decarboxylation.

(c) The decarboxylation of acetoacetic acid is catalyzed by primary amines (amines of the form R¬NH₂). Explain. H3C 2 OH acetoacetic acid

HO + PhNH || HC + HO H 3-(N-phenylimino)butanoic acid (a -imino carboxylic acid) zwitterion form Figure

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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Question Posted: Dec 07, 2023 07:08 AM

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-Imino carboxylic acids such as the one in Fig. P20.53 decarboxylate very rapidly provided that the pH...

Question:

H3C Н2 OH acetoacetic acid

Step by Step Answer:

a The protonated imine nitrogen serves as an electron sink that accepts electrons from the departing ...View the full answer

Organic Chemistry

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