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Amine Chemistry
Amines have general formula R-NH2 and are organic derivatives of ammonia
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Primary Amine- N bonded to one alkyl group
Methylamine/ Amminomethane
Secondary Amine- N bonded to two alkyl groups
Dimethylamine/ Methylaminomethane
Tertiary Amine- N bonded to three alkyl groups
Trimethylamine/ Dimethylaminomethane
Amines can act as bases due to lone pair of electrons on nitrogen atom
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Relative Base Strength
The relative base strength is determined by how available the lone pair on the nitrogen is for
protonation
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So methylamine is more basic than ammonia
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So ammonia is more basic than phenylamine
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They will undergo nucleophilic substitution reactions with haloalkanes
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Ammonia acts as nucleophile and substitute the bromine, an ethylammonium salt is produced;
NH3 + CH3CH2Br CH3CH2NH3+BrThe salt then undergoes proton exchange with another molecule of ammonia to produce the
primary amine and Ammonium Bromide salt
CH3CH2NH3+Br- + NH3 CH3CH2NH2 + NH4Br
Step 2
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Secondary amine can also react with haloalkane present to form a tertiary ammonium salt
(CH3CH2)2NH + CH3CH2Br (CH3CH2)3NH+BrTertiary ethylammonium salt will also undergo proton exchange with ammonia to produce a tertiary
amine
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Tertiary amine can also react with bromoethane to form a quaternary ammonium salt
(CH3CH2)3N + Ch3CH2Br [(CH3CH2)4N]+BrAmmonia + Haloalkanes produces a range of products which may be a disadvantage as it requires
separation
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A large excess of ammonia will favour formation of
the primary amine
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The addition reaction can be achieved by using lithium tetrahydridoaluminate (LiAlH 4) dissolved in
dry ethoxyethane, followed by aqueous hydrolysis
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Reduction of Nitrobenzene
6 hydrogen ions of 3 hydrogen molecules are needed