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?

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Treatment of a carboxylic acid with trifluoraacetic anhydride leads to an
unsymmetrical anhydride that rapidly reacts with an alcohol to give an ester.
Q5.
F3C
CF3
trifluoroacetic anhydride
CH;CH,OH
H3C
+ 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?
Transcribed Image Text:Treatment of a carboxylic acid with trifluoraacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with an alcohol to give an ester. Q5. F3C CF3 trifluoroacetic anhydride CH;CH,OH H3C + 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?
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