Amines

• Amines are produced when one or more of the hydrogen atoms in ammonia is replaced by an organic group either by nucleophilic substitution or by the reduction of nitriles.
• Primary amines have one organic group, secondary amines have two, and tertiary amines have all three bonds as organic groups.
• Amines can be produced by nucleophilic substitution by the reaction of halogenoalkane with ammonia, producing a primary amine and an ammonium salt.
• Nucleophilic substitution can also occur with primary amines to form secondary amines, secondary to form tertiary and tertiary to form a quaternary ammonium salt.
• Ammonia can be added in excess to a nucleophilic substitution reaction in order to only produce a primary amine, or the mixture of products can be separated using fractional distillation.
• Nitriles can be reduced via hydrogenation to produce amines, requiring LiAlH4, a reducing agent and acidic conditions, or hydrogen and nickel (catalytic hydrogenation).
• Aromatic amines can be produced from the reduction of nitrobenzene using concentrated hydrochloric acid and a tin catalyst.
• Cationic surfactants are complexes with a positive and negative end, making them good conditioners as the two ends are attracted to different substances, preventing static building up on surfaces.
• Amines are weak bases because the lone electron pair on the nitrogen atom can accept protons.
• The inductive effect is how different functional groups can affect how available a lone electron pair is by changing the electron density around the bond.
• Benzene rings draw electron density towards them and alkyl groups push the electron density away from them.
• Aliphatic amines are stronger bases than aromatic amines due to the inductive effect of an alkyl group vs a benzene ring.
• Amines can act as nucleophiles because the lone electron pair is attracted to partially positive regions on other molecules.
• Amines can undergo nucleophilic addition-elimination reactions with acyl chlorides to produce amides and N-substituted amides.
• Amines can undergo nucleophilic addition-elimination with acid anhydrides to produce an amide and a carboxylic acid.
• An N-substituted amide is an amide group with an alkyl group attached to the nitrogen atom.
• N-substituted amides are named in a similar way to esters: N - [prefix of group directly attached to nitrogen] [prefix of alkyl group] amide.
• In nucleophilic addition-elimination, a nucleophile attacks the carbon with a double bond oxygen. One of the double bond breaks and the oxygen becomes negative. The chlorine (acyl chlorides) or alkyl (acid anhydrides) group is eliminated and the double bond reforms.