Carboxylic Acids. Nomenclature of Carboxylic Acids Esters.

Carboxylic Acids

Nomenclature of Carboxylic Acids

Esters

Cyclic Esters Are Known as Lactones

Amides

Carboxylic acids have relatively high boiling points because of intermolecular hydrogen bonds

Amides have the highest boiling points

Acidity

Substituent Effects on Acidity

COOH

OCH3

COOH COOH

NO2

COOH

NO2

COOH

NO2

p-methoxy benzoic acid m-nitro p-nitro o-nitro

pKa = 4.46 pKa = 4.19 pKa = 3.47 pKa = 3.41 pKa = 2.16

Purifying an Acid by extraction

All carboxylic acid derivatives react by the same generalmechanism

The tetrahedral intermediate eliminates the weakest base

tetrahedral intermediate

Reactions of Acyl Halides

Reactions of Acid Anhydrides

Reactions of Esters

a hydrolysis reaction

a transesterification

Fats and Oils Are Triesters of Glycerol

Nucleophilic Acyl Substitution of Carboxylic Acids

Hydrolysis of Amides

The acyl halide can be used to prepare other carboxylicacid derivatives

Urea and Urethanes

• Urea is the diamide of carbonic acid.

• Urethanes are esters of a monoamide of carbonic acid.

+C

O

ClCl C

O

NH2H2N2 NH3urea

N C O

H2ONH C OH

O

a carbamic acid

ROHNH C OR

O

a urethane