Chapter 18

Question 1

structure of acid halides

Answer 1

• functional group is acyl group bonded to halide
• carbonyl group bonded to halogen atom
• most common is acid chlorides
• -ic acid to -yl halide

Question 2

preparation of acid halides

Answer 2

treat a carboxylic acid with thinoyl chloride (SOCl2)

Question 3

mechanism for acid halides

Answer 3

1. Reaction with SOCl2 transforms OH, a poor leaving group, into a chlorosulfite group, a good leaving group.
2. Attack of chloride ion gives a tetrahedral carbonyl addition intermediate, which collapses to give the acid chloride.

Question 4

sulfonyl chlorides

Answer 4

Replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride.

Question 5

acid anhydrides

Answer 5

• 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.

Question 6

phosphoric anhydrides

Answer 6

contains two phosphoryl groups bonded to an oxygen atom

Question 7

esters

Answer 7

• 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

Question 8

lactone

Answer 8

a cyclic ester

-name the parent carboxylic acid, drop the suix -ic acid-ic acidand add -olactone

Question 9

phosphoric acid

Answer 9

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.

Question 10

amides

Answer 10

-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–.

Question 11

lactams

Answer 11

cyclic amide

-Name the parent carboxylic acid, drop the suix -ic acid-ic acidand add -lactam-lactam.

Question 12

imides

Answer 12

-functional group: 2 acyl groups bonded to nitrogen atom

-

Question 13

nitriles

Answer 13

-functional group: cyano group
-IUPAC names: name as an alkanenitrilealkanenitrile.
–common names: drop the -ic acid-ic acidand add -onitrile-onitrile.