structure of acid halides
- functional group is acyl group bonded to halide
- carbonyl group bonded to halogen atom
- most common is acid chlorides
- -ic acid to -yl halide
preparation of acid halides
treat a carboxylic acid with thinoyl chloride (SOCl2)
mechanism for acid halides
- Reaction with SOCl2 transforms OH, a poor leaving group, into a chlorosulfite group, a good leaving group.
- Attack of chloride ion gives a tetrahedral carbonyl addition intermediate, which collapses to give the acid chloride.
sulfonyl chlorides
Replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride.
acid anhydrides
- 2 acyl groups bonded to an oxygen atom
- must be symmetrical or mixed
- replace “acid” with “anhydride”
- Cyclic anhydrides are named from the dicarboxylic acids from which they are derived.
phosphoric anhydrides
contains two phosphoryl groups bonded to an oxygen atom
esters
- functional group: acyl group bonded to -OR or -OAr
- Name the alkyl or aryl group bonded to oxygen, followed by the name of the acid.
- change -ic acid to -ate
lactone
a cyclic ester
-name the parent carboxylic acid, drop the suix -ic acid-ic acidand add -olactone
phosphoric acid
Phosphoric acid forms mono-, di-, and triesters.
–Name by giving the name of the alkyl or aryl group(s) bonded to oxygen followed by the word phosphatephosphate.
amides
-functional group: acyl group bonded to nitrogen atom
-IUPAC: drop -oic acidoic acidfrom the name of the parent acid and add -amide-amide. For the common name, drop -ic ic of the parent name and add -amide-amide
.–if the amide nitrogen is bonded to an alkyl or aryl group, name the group and show its locaion on nitrogen by NN–.
lactams
cyclic amide
-Name the parent carboxylic acid, drop the suix -ic acid-ic acidand add -lactam-lactam.
imides
-functional group: 2 acyl groups bonded to nitrogen atom
-
nitriles
-functional group: cyano group
-IUPAC names: name as an alkanenitrilealkanenitrile.
–common names: drop the -ic acid-ic acidand add -onitrile-onitrile.
