ORGANIC CHEMISTRY (PETRO)

ORGANIC CHEMISTRY
Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 8647256 ext. 5681
Email:
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Chapter 13:

AMINES-DIAZONIUM
SALTS

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NOMENCLATURE OF AMINES

Common names: alkyl + amine

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IUPAC names: alkan + amine

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Substituents are listed in alphabetical order,

regardless of whether they are attached to the
nitrogen or the hydrocarbon
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PREPARATIONS OF AMINES

Alkylation of ammonia

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Gabriel synthesis of primary amines

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Amines by reduction

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Preparation of arylamines

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1:1 molar ratio

• It is possible to selectively reduce just 1 of 2

nitro groups using S2• H2 /Pd, Fe/HCl… will reduce both nitro groups10


Amines
by
reductive
amination

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Amines by Hoffman Rearrangement

Have 1 less
carbon atom

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BASICITY OF AMINES

NOTE:
•pKa of conjugate
acid
• in water at 25 oC

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REACTIONS OF AMINES

Reactions
with
primary
amines

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Reactions with secondary amines

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Reactions with carboxylic acid derivatives

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Reactions with alkyl halides

Nucleophilic
substitution
reaction
Excess amine

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The Hofmann elimination reaction

Quaternary ammonium hydroxide formation
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Different from Zaitsev’s product

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Oxidation reactions

Amines can be oxidized by hydrogen peroxide,
peroxyacids, other common oxidizing agents
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Reaction of primary amines with HNO2
HNO2 is unstable, aqueous
NaNO2 / acid should be used
Stable
NOT stable

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Mechanism:

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Alkyl diazonium salt is NOT stable

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REACTIONS OF DIAZONIUM SALTS
Sandmeyer reactions

KCl, KBr can NOT be used in place of CuCl, CuBr
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