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
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