CH 18 - Carboxylic Acid Derivatives

nomenclature - acid halide

-yl halide in place of acid

nomenclature - acid anhydride

anhydride in place of acid

nomenclature - ester

replace ic acid with -ate

• name group on O before the ester root name

nomenclature - cyclic esters

root based on longest carbon chain, position of ester O indicated with number of greek letter nom

nomenclature - amide

replace -ic acid with -amide

• name groups on N before the amide root name

• use N to indicate group is attached to the N

cyclic amines

root based on carbon chain, position of ester N indicated with number or greek letter

imides nomenclature

replace -ic acid with -imide

• N substituents named like amides

nomenclature - nitrile

replace -oic acid with -nitrile

• count C in CN as part of root

amides are significantly more acidic than

amines

amide

ketone bonded to N

amine

single bond (N)

like aldehydes/ketones, carboxylic acid derivatives have

electrophilic carbon that undergoes nucleophilic addition

unlike aldehydes/ketones, the end product is

a carbonyl, not an alcohol

nucleophilic addition to carboxylic acid derivates results in a

substitution reaction, rather than addition th

nucleophilic acyl addition - reaction only proceeds if the

product is less reactive than the starting material

all carboxylic acid derivatives can be converted to a carboxylic acid by

hydrolysis, often under acidic or basic conditions