Question: There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The following method converts the acid to an N-hydroxysuccinimide

There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The following method converts the acid to an N-hydroxysuccinimide (NHS) ester.

(a) Explain why an NHS ester is much more reactive than a simple alkyl ester.
(b) Propose a mechanism for the reaction shown.
(c) Propose a mechanism for the reaction of the NHS ester with an amine, R - NH2.

+ F3C O-N O-N NHS ester

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