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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
All carboxylic acid derivatives react by the same generalmechanism
The tetrahedral intermediate eliminates the weakest base
tetrahedral intermediate