Chapter 22: Amines

Amines (e.g. RNH₂) are organic derivatives of ammonia, NH₃ (i.e. replace the N-H with N-C bonds) and so they have certain similarities with ammonia (e.g. basicity, nucleophilicity).

Nitrogen containing compounds are biologically very important (examples) amines, amino acids, amides, proteins, vitamins etc.

The important organic reactions of amines (nucleophiles) are with the common electrophiles as we have already encountered:

• via nucleophilic substitution with alkyl halides
• via nucleophilic addition aldehydes or ketones
•  via nucleophilic acyl substitution with carboxylic acid derivatives, especially acid chlorides or anhydrides

• Nomenclature
• Physical Properties
• Structure
• Reactivity
• Basicity

• Overview of alkylations
• Alkylation of Ammonia by Alkyl Halides
• Alkylation of Phthalimide (Gabriel synthesis of primary amines)
• Reductions of nitrogen containing functional groups:
• Azides
• Nitriles
• Nitro
• Amides
• Reductive Amination via Imines

• Overview
• Alkylation of Amines by Alkyl Halides
• Reaction of Amines with Aldehydes and Ketones
• Preparation of Amides
• Hofmann Elimination
• Electrophilic Aromatic Substitution of Aryl Amines
• Nitrosation
• Transformations of Aryl Diazonium salts

• IR
• 1H NMR
• 13C NMR
• UV-VIS
• Mass Spectrometry

• Sample Problems

© Dr. Ian Hunt, Department of Chemistry