CHEM-2221 Lecture Notes - Lecture 19: Nucleophilic Acyl Substitution, Grignard Reaction, Aminolysis
27 May 2016
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Document Summary
Nomenclature of acid chlorides: replace the -ic acid ending of the iupac name of the corresponding carboxylic acid by yl chloride, the suffix -carbonyl chloride is used for attachments to rings other than benzene. Nomenclature of amides: when naming amides, replace the -ic acid or -oic acid of the corresponding carboxylic acid with -amide, substituents are listed in alphabetical order. Substitution on nitrogen is indicated by the locant n- 19. 2 structure and reactivity of carboxylic acid derivatives. Stabilization of the carbonyl: stabilization depends on resonance. Amides: amides have restricted rotation around the c-n bond. Acyl chlorides: anhydride formation - acid chlorides react with carboxylic acids to give acid anhydrides, alcoholysis - acid chlorides react with alcohols to give esters, 1 alcohols react faster than 2 alcohols, which react faster than 3 alcohols. Acyl chlorides: aminolysis - reaction of acid chlorides with ammonia, 1 or 2 amines to afford amides, hydrolysis - acid chlorides react with water to afford carboxylic acids.
