Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions

Carboxylic Compounds
?Acyl group bonded to Y, an electronegative atom or leaving group
?Includes: Y = halide (acid halides), acyloxy (anhydrides), alkoxy (esters), amine (amides), thiolate (thioesters), phosphate (acyl phosphates)
General Reaction Pattern
?Nucleophilic acyl substitution
Why this Chapter?
?Carboxylic acids are among the most widespread of molecules.
?A study of them and their primary reaction “nucleophilic acyl substitution” is fundamental to understanding organic chemistry
21.1 Naming Carboxylic Acid Derivatives
?Acid Halides, RCOX
?Derived from the carboxylic acid name by replacing the -ic acidending with -ylor the -carboxylic acidending with –carbonyland specifying the halide
Naming Acid Anhydrides, RCO2COR
?If symnmetrical replace “acid”with “anhydride” based on the related carboxylic acid (for symmetrical anhydrides)
?From substituted monocarboxylic acids: use bis-ahead of the acid name
?Unsymmetrical anhydrides—cite the two acids alphabetically
Naming Amides, RCONH2
?With unsubstituted ?NH2group. replace -oic acidor -ic acidwith -amide, or by replacing the -carboxylic acidending with –carboxamide
?If the N is further substituted, identify the substituent groups (preceded by “N”) and then the parent amide