Reactions of Amines and

Amides
 Reactions of Amines
Ammonia (NH3) acts as a base because the nitrogen
atom has a lone pair of electrons that can accept a
proton. Amines also have a lone electron pair on their
nitrogen atoms and can accept a proton from water
to form substituted ammonium (NH4+) ions and
hydroxide (OH−) ions:
As a specific example, methylamine reacts with water
to form the methylammonium ion and the OH−ion.
 Reactions of Amines
Nearly all amines, including those that are not
very soluble in water, will react with strong acids
to form salts soluble in water.

Amine salts are named like other salts: the name of

the cation is followed by the name of the anion.
 Reactions of Amines
Primary, secondary, and tertiary amines can be alkylated
by reaction with alkyl halides.
Primary and secondary (but not tertiary) amines can also
be acylated by nucleophilic acyl substitution reactions
with acid chlorides or acid anhydrides to give amides.
 Reactions of Amides
The most common reactions of amides are their
hydrolysis to give carboxylic acids and their
reduction with LiAlH4. Interestingly, though, the
reduction product of an amide is an amine rather
than the expected alcohol
 Conversion of Amides into Acids
(RCONH2  RCO2H)
Amides undergo hydrolysis in either aqueous acid or base
to yield carboxylic acids plus amine. Although the reaction
is slow and requires prolonged heating,the overall
transformation is a typical nucleophilic acyl substitution of
OH for NH2. In biochemistry, the reaction is particularly
useful for hydrolyzing proteins to their constituent amino
acids.
Conversion of Amides into Amines by
Reduction (RCONH2 n RCH2NH2)
Like other carboxylic acid derivatives, amides are
reduced by LiAlH4. The product of this reduction,
however, is an amine rather than an alcohol

The effect of amide reduction is to convert the amide

carbonyl group into a methylene group (C=O  CH2).
This kind of reaction is specific for amides and does not
occur with other carboxylic acid derivatives