Amines and Amides Cheat Sheet

Amines are organic compounds containing nitrogen, derived from ammonia, and are classified by the number of alkyl/aromatic groups attached to the nitrogen. Amides are derivatives of carboxylic acids where the hydroxyl group is replaced by a nitrogen group. Both classes have distinct naming conventions, properties, and reactions.

Core Principles

• Amines are derivatives of ammonia (NH3) with one or more H atoms replaced by alkyl or aromatic groups.
• Amides are derivatives of carboxylic acids where -OH is replaced by -NH2, -NHR, or -NR2.
• Amines can be primary (1°), secondary (2°), or tertiary (3°) based on N substitution.
• IUPAC naming for amines involves replacing the 'e' of the parent alkane with 'amine'.
• IUPAC naming for amides involves replacing 'oic acid' or 'ic acid' with 'amide'.
• Alkyl groups on the nitrogen of amides are named with the prefix 'N-'.
• Amines act as weak bases in water.
• Amides have higher melting points than alkanes but lower than alcohols.
• Amides can undergo hydrolysis (acid or base catalyzed) to form carboxylic acids/salts and amines/ammonia.
• Heterocyclic amines contain nitrogen atoms within a ring structure.
• Alkaloids are naturally occurring amines with physiological activity.

Action Steps

• Identify the longest carbon chain attached to the nitrogen for IUPAC amine naming.
• Replace the final 'e' of the alkane name with 'amine'.
• Number the carbon chain to indicate the position of the -NH2 group and any substituents.
• For N-substituted amides, name the alkyl group(s) attached to nitrogen with the prefix 'N-'.
• Determine amine classification (primary, secondary, tertiary) by counting carbons bonded to nitrogen.
• Recognize heterocyclic amines by the presence of nitrogen within a ring.
• Predict hydrolysis products by breaking the amide bond and adding H2O (acid) or NaOH (base).

Formulas

• General amine structure: R-NH2 (primary), R2NH (secondary), R3N (tertiary)
• General amide structure: R-C(=O)-NH2 (primary), R-C(=O)-NHR (secondary), R-C(=O)-NR2 (tertiary)
• Amine reaction with water (base): R-NH2 + H2O <=> R-NH3+ + OH-
• Acid hydrolysis of amide: R-C(=O)-NR'R'' + H2O + HCl --Heat--> R-C(=O)-OH + R'NH3+Cl-
• Base hydrolysis of amide: R-C(=O)-NR'R'' + NaOH --Heat--> R-C(=O)-O-Na+ + R'NH2

Key Terms

• Amine: Organic compounds derived from ammonia with one or more hydrogen atoms replaced by alkyl or aromatic groups.
• Amide: Organic compounds containing a carbonyl group bonded to a nitrogen atom.
• Primary Amine (1°): An amine where the nitrogen atom is bonded to one alkyl/aromatic group and two hydrogen atoms.
• Secondary Amine (2°): An amine where the nitrogen atom is bonded to two alkyl/aromatic groups and one hydrogen atom.
• Tertiary Amine (3°): An amine where the nitrogen atom is bonded to three alkyl/aromatic groups and no hydrogen atoms.
• Heterocyclic Amine: A cyclic organic compound containing nitrogen atoms within the ring.
• Alkaloid: Naturally occurring amine compounds produced by plants, often with physiological effects.
• Amidation: The reaction forming an amide, typically from a carboxylic acid and an amine/ammonia with heat.
• Hydrolysis: The reaction of an amide with water (catalyzed by acid or base) to break the amide bond.