Conversion of carboxylic acids to amide using DCC as an activating agent
المؤلف:
University of Missouri System
المصدر:
Organic Chemistry ii
الجزء والصفحة:
.................
19-10-2020
4587
Conversion of carboxylic acids to amide using DCC as an activating agent
The direct conversion of a carboxylic acid to an amide is difficult because amines are basic and tend to convert carboxylic acids to their highly unreactive carboxylates. In this reaction the carboxylic acid adds to the DCC molecule to form a good leaving group which can then be displaced by an amine during nucleophilic substitution. DCC induced coupling to form an amide linkage is an important reaction in the synthesis of peptides.
Going from reactants to products simplified
Mechanism
1) Deprotonation
2) Nucleophilic attack by the carboxylate
3) Nucleophilic attack by the amine
4) Proton transfer
5) Leaving group removal
الاكثر قراءة في مواضيع عامة في الكيمياء العضوية
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