Treatment of a carboxylic acid with triflwergacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with an alcohol to give an ester. Q5. F3C O. CF3 trifluoroacetic anhydride CH;CH,OH HạC + CF,CO,H HO, H3C CF3 H3C OCH2CH3 Unsymmetrical anhydride 1 Ethyl ester 2 (a) Propose a mechanism, using curved arrows, for the formation of the unsymmetrical anhydride 1. (b) Propose a mechanism, using curved arrows, for the formation of the ethyl ester 2. (c) Why is the unsymmetrical anhydride unusually reactive?

Treatment of a carboxylic acid with triflwergacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with an alcohol to give an ester. Q5. F3C O. CF3 trifluoroacetic anhydride CH;CH,OH HạC + CF,CO,H HO, H3C CF3 H3C OCH2CH3 Unsymmetrical anhydride 1 Ethyl ester 2 (a) Propose a mechanism, using curved arrows, for the formation of the unsymmetrical anhydride 1. (b) Propose a mechanism, using curved arrows, for the formation of the ethyl ester 2. (c) Why is the unsymmetrical anhydride unusually reactive?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 27MP

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