(CHEM 3111) Amides

Preparation of Amines (alkyl halide)

Alkyl halide

1) NaCN

2) xs LiAlH₄

3) H₃O⁺

Amine

Preparation of Amines (carboxylic acids)

Carboxylic acid

1) SOCl₂

2) xs NH₃

3) xs LiAlH₄

4) H₃O⁺

Amine

Preparation of Aniline

Benzene

1) HNO₃, H₂SO₄

2) Fe, H₃O⁺

3) NaOH

Aniline

Azide Synthesis of Amines

Alkyl halide

1) NaN₃

2) LAlH₄

3) H₃O⁺

Amine

Gabriel Synthesis of Amines

Phthalimide

1) KOH

2) RX

3) H₃O⁺

Amine

Reductive Amination

Carbonyl

1) NH₃ or RNH₂ or R₂NH, [H⁺], NaBH₃CN

Amine

Acylation of Amines

Amine

1) Acyl chloride

Amide

Alkylation of Aniline

Aniline

1) Acyl chloride

2) RCl, AlCl₃

3) H₃O⁺

Para-alkylaniline

Hofmann Elimination

Amine

1) xs CH₃I

2) Ag₂O, H₂O, heat

Diazonium Synthesis

Amine

1) NaNO_2, HCl

Diazonium salt

Aryl Diazonium → Aryl Halogen

1) CuX

Aryl Diazonium → Aryl Hydrogen

1) H₃PO₂

Aryl Diazonium → Aryl Nitrile

1) CuCN

Aryl diazonium → aryl fluorine

HBF₄, heat

Azo Coupling

Activated aromatic ring + aryl diazonium