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amides
organic molecules which contain a carbonyl to nitrogen single bond
amide bond
bond that breaks when amides are hydrolysed - amide bond is also called a peptide bond
physical properties
amides are quite polar and have very strong intermolecular forces - high BP
chemical properties
amides are not proton acceptors (bases)
the carbonyl attracts the lone pair on nitrogen to prevent it from bonding to H+
amide preparation
amines + carboxylic acids
amines + acid chlorides
amines + carboxylic acids
poor method of preparation
poor reactivity of carboxylate group towards nucleophilic substitution
amines + acid chlorides
works for primary amines, secondary amines and ammonia
leaving group (Cl-)
excess of amine to neutralise all HCl
acidic hydrolysis
amine product is converted into its ammonium salt
basic hydrolysis
carboxylic acid product is converted into its carboxylate salt
biological hydrolysis
enzymes catalyse amide hydrolysis - digestion of proteins
amide bonds are readily cleaved in the stomach - pectin