AQA Chemistry A-Level
3.3.11: Amines
Detailed Notes
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3.3.11.1 - Preparation of Amines
Amines are produced when one or more of the hydrogen atoms in ammonia is replaced with
an organic group. They can be 1o , 2o or 3o amines depending on how many hydrogen atoms
are replaced.
Example:
Amines can be produced in two ways.
Nucleophilic Substitution
This reaction produced amines from the reaction of a halogenoalkane with ammonia in a
sealed tube. One mole of halogenoalkane reacts with two moles of ammonia producing a
primary amine and an ammonium salt.
Example:
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This substitution reaction can continue until all the hydrogen atoms have been replaced with
organic groups. Following this, an additional substitution can occur, producing a quaternary
ammonium salt.
Example:
The multiple number of possible substitutions means that a mixture of products are produced.
Therefore the reaction has low efficiency and reaction conditions have to be changed so that
only a single substitution occurs. Ammonia can be added in excess in order to achieve only the
primary amine, or the mixture of products can be separated using fractional distillation.
Reduction of Nitriles
Reducing nitriles via hydrogenation can produce amines. This reduction require LiAlH4, a
reducing agent, and acidic conditions or a combination of hydrogen and nickel (catalytic
hydrogenation).
Example:
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Aromatic Amines
These can be produced from the reduction of nitrobenzene using concentrated hydrochloric
acid (HCl) and a tin catalyst.
Example:
Cationic Surfactants
These molecules are complexes with a positive and negative end. This makes them good
conditioners as the two ends are attracted to different substances, preventing static from
building up on surfaces. Cationic surfactants are therefore useful in industry.
Example:
3.3.11.2 - Amine Base Properties
Amines are weak bases because the lone electron pair on the nitrogen atom can accept
protons. The base strength of amines depends on how available the electron pair is on the
molecule. The more available the electrons, the more likely it is to accept a proton meaning it is
a stronger base.
The Inductive Effect
In an organic molecule, different functional groups can affect how available a lone electron pair
is by changing electron density around the bond.
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1. Benzene rings - draw electron density away from the nitrogen making it ‘less available’
Example:
Negative inductive effect.
2. Alkyl groups - push electron density towards the nitrogen making it ‘more available’.
More alkyl groups means more ‘pushing’.
Example:
Positive inductive effect.
This means aliphatic amines are stronger bases and aromatic amines are weaker.
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3.3.11.3 - Nucleophilic Properties
Nucleophilic Substitution
Amines can act as nucleophiles because the lone electron pair is attracted to ∂+ regions on
other molecules. This mean amines can substitute halides on halogenoalkanes to form 1o, 2o
or 3o amines and quaternary ammonium salts.
Nucleophilic Addition-Elimination
Amines can also undergo nucleophilic addition-elimination reactions with acyl chlorides to
produce amides and N-substituted amides.
Mechanism
This same reaction mechanism can also occur with acid anhydrides to produce an amide and
a carboxylic acid.
N-substituted Amides
When naming n-substituted amides, they are treated in a similar way to esters.
Example:
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