amides

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10 Terms

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amides

organic molecules which contain a carbonyl to nitrogen single bond

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amide bond

bond that breaks when amides are hydrolysed - amide bond is also called a peptide bond

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physical properties

amides are quite polar and have very strong intermolecular forces - high BP

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chemical properties

amides are not proton acceptors (bases)

the carbonyl attracts the lone pair on nitrogen to prevent it from bonding to H+

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amide preparation

  1. amines + carboxylic acids

  2. amines + acid chlorides

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amines + carboxylic acids

poor method of preparation

poor reactivity of carboxylate group towards nucleophilic substitution

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amines + acid chlorides

works for primary amines, secondary amines and ammonia

leaving group (Cl-)

excess of amine to neutralise all HCl

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acidic hydrolysis

amine product is converted into its ammonium salt

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basic hydrolysis

carboxylic acid product is converted into its carboxylate salt

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biological hydrolysis

enzymes catalyse amide hydrolysis - digestion of proteins

amide bonds are readily cleaved in the stomach - pectin