Bài giảng Organic chemistry - Chapter 13: Amines-diazonium salts - Phan Nam
ORGANIC CHEMISTRY
Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 38647256 ext. 5681
Email: [email protected].vn
1
Chapter 13: AMINES-DIAZONIUM
SALTS
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NOMENCLATURE OF AMINES
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Common names: alkyl + amine
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 groups
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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
Reactions with alkyl halides
Nucleophilic
substitution
reaction
Excess amine
The Hofmann elimination reaction
Quaternary ammonium hydroxide formation
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Different from Zaitsev’s product
Oxidation reactions
Amines can be oxidized by hydrogen peroxide,
peroxyacids, other common oxidizing agents
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