Chapter 17: Carboxylic acids and their derivatives

Carboxylic acid

is a compound that has a carbonyl group bonded to an ¬OH group, RCOOH.

Dacron

is an example of a polyester, while Nylon is an example of a polyamide.

Ester

is a compound that has a carbonyl group bonded to an ¬OR′ group, RCOOR′.

Esterification

is the reaction between an alcohol and a carboxylic acid to yield an ester plus water.

¬OH groups

It may be esterified at one, two, or all three of its by reaction with an alcohol.

sodium

With strong bases, such as hydroxide, a carboxylic acid reacts to give water and a carboxylic acid salt.

Compounds

with a nitrogen directly attached to the carbonyl carbon atom are amides.

Amides

are extremely stable in water but do undergo hydrolysis with prolonged heating in the presence of acids or bases.

Saponification

is the reaction of an ester with aqueous hydroxide ion to yield an alcohol and the metal salt (usually sodium or potassium) of a carboxylic acid.

Polyesters

and polyamides are formed when a dicarboxylic acid is allowed to react with either a dialcohol or a diamine, respectively.

Volatile acids

have strong, sharp odours while volatile esters have pleasant, fruity odours.

carboxylic acids

Since , esters, and amides all contain a carbonyl carbon atom (C= O) bonded either to an oxygen or to a nitrogen, they are all polar.

Amide

is a compound that has a carbonyl group bonded to a nitrogen- atom group, RCONR′ 2, where the R′ groups may be alkyl groups or hydrogen atoms.

Esters

and amides are made from carboxylic acids.

Carboxylic acids

, primary amides, and secondary amides exhibit strong hydrogen bonding to one another; esters and tertiary amides do not hydrogen bond to one another.

carboxylic acids

All and their derivatives, however, can still hydrogen bond to water molecules.

acyl group

The portion of the carboxylic acid that does not change during a carbonyl-group substitution reaction

carboxylate anion

anion that results from ionization of a carboxylic acid, RCOO-