Ch 20

A molecule containing an amino group, -NH2 , -NHR, or -NR2 , obtained by removing one or more hydrogen atoms from ammonia, with the general formula RNH2 , RNHR, or RNR2 . A primary amine has one R group attached to the N atom, a secondary amine has two R groups attached to the N atom, and a tertiary amine has three R groups attached to the N atom.

An amine that has one or more alkyl groups attached to the amine nitrogen, such as RNH2

The -NH2 group; if alky1ated, it becomes an alkylamino group -NHR, or a dialkylamino group -NR2

An amine that has one or more aromatic groups attached to the amine nitrogen, such as ArNH2

A derivative of an amine with a positively charged nitrogen atom having four bonds; an amine is protonated by an acid to give an ammonium salt: RNH2 + HA → RN+H3 A- ; a quaternary ammonium salt has a positively charged nitrogen atom bonded to four alkyl (or aryl) groups: R4N+

 A compound having the azido group, -N3

Synthesis of primary amines by alkylation of the potassium salt of phthalimide, followed by displacement of the amine by hydrazine

The reduction of an imine or oxime derivative of a ketone or aldehyde to an amine.

A compound with a carbon-nitrogen double bond, R2C=NR', formed by the reaction of a ketone or aldehyde with a primary amine; a substituted imine is often called a Schiff base.

Conversion of a primary carboxylic amide to a primary amine, with one fewer carbon atom, by treatment with bromine in aqueous NaOH, via an isocyanate intermediate

Conversion of a carboxylic acid to an amine having one fewer carbon atoms, which proceeds via thermal decomposition of an acyl azide into an isocyanate

The reaction of a primary aromatic amine with nitrous acid, HNO2 , which forms a diazonium ion, R-N+≡N: and can be used to prepare aryl halides, phenols, and aryl cyanides, or to deaminate the amine

Ion of the type R-N+≡N: Aryl diazonium ions are formed by treatment of primary aromatic amines with nitrous acid, HNO2 , which can be used to prepare aryl halides, phenols, and aryl cyanides, or to deaminate the amine

An amine with a nitroso group -N=O bonded to the amine nitrogen atom; the reaction of secondary amines with nitrous acid gives secondary nitrosoamines.

Replacement of the -N≡N group in an arenediazonium salt by a cuprous salt; usually cuprous chloride, bromide, or cyanide

The use of an electrophilic diazonium salt in electrophilic aromatic substitution, such as the reaction of an aryl diazonium salt with an arene, which forms a compound of the type ArN=NAr'. The arene must be strongly activated toward electrophilic aromatic substitution; that is, it must bear a powerful electron-releasing substituent such as -OH or -NR2 .

An amide of a sulfonic acid, which is the nitrogen analogue of a sulfonate ester.

The reaction of an amine with benzenesulfonyl chloride to form a benzenesulfonamide, in order to determine whether it is a primary, secondary, or tertiary amine.

Elimination of a quaternary ammonium hydroxide by pyrolysis into an alkene and a tertiary amine, which usually gives the least-substituted alkene (Hofmann product)

The major product of an elimination reaction that uses a bulky, strong base will be the less stable alkene, which has the less substituted double bond.

 Pyrolysis of a tertiary amine oxide into an alkene and a hydroxylamine.

An amine that occurs naturally in many plants, fungi and bacteria, and has profound physiological effects on animals, often toxic; the name derives from the word alkaline, since these compounds are weak bases with a bitter taste