Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with

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Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with alcohol to give an ester.

(a) Propose a mechanism for formation of the unsymmetrical anhydride.

(b) Why is the unsymmetrical anhydride unusually reactive?

(c) Why does the unsymmetrical anhydride react as indicated rather than giving a trifluoroacetate ester plus carboxylicacid?

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Organic Chemistry

ISBN: 9780495112587

7 Edition

Authors: John McMurry

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Question Posted: Feb 28, 2011 04:55 AM

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Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with

Question:

R'OH (CF3CO20 CF3CO2H OR' CF3 он

Step by Step Answer:

0 HO OCOCF3 addition of carboxylic acid F3C 0 HC Q OCOCF3 R F30000 GOCOCF...View the full answer

Organic Chemistry

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