Chapter 22 Reagents

1. NaCN

2. xs LiAlH₄

3. H₂O

Preparation of an amine (from an alkyl halide)

1. SOCl₂

2. xs NH₃

3. xs LiAlH₄

4. H₂O

Preparation of an amine (from a carboxylic acid)

1. Fe, H₃O⁺

2. NaOH

NO2 aromatic ring to NH2 aromatic ring

1. NaN₃

2. LiAlH₄

3. H₂O

convert an alkyl halide into an amine, without a change in the carbon skeleton

Gabriel

prepare primary amines

NaBH3CN

This process can be used to convert a primary amine into a secondary amine. Similarly, a secondary amine is converted into a tertiary amine

acetyl chloride

An amine will undergo acetylation (giving an amide) when treated with acetyl chloride.

1. Excess CH₃I

2. Ag₂O, H₂O, heat

These reagents can be used to achieve elimination of H and NH₂ to give an alkene. When there are two possible regiochemical outcomes for the elimination process, the less substituted alkene predominates.

NaNO2, HCl

A mixture of sodium nitrite and HCl will convert a primary amine into a diazonium salt. Under the same conditions, a secondary amine is converted into an N-nitrosamine.

HBF4

When an aryldiazonium salt is treated with HBF₄, the diazonium group is replaced with a fluorine atom

H2O, heat

Preparation of phenol. When an aryldiazonium salt is treated with water and heat, the diazonium group is replaced with an OH group.

H3PO2

When an aryldiazonium salt is treated with H3PO2, the diazonium group is replaced with a hydrogen atom