Tài liệu Bài giảng organic chemistry chapter13

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] 1 Chapter 13: AMINES-DIAZONIUM SALTS 2 NOMENCLATURE OF AMINES Common names: alkyl + amine 3 IUPAC names: alkan + amine 4 Substituents are listed in alphabetical order, regardless of whether they are attached to the nitrogen or the hydrocarbon 5 PREPARATIONS OF AMINES Alkylation of ammonia 6 Gabriel synthesis of primary amines 7 Amines by reduction 8 Preparation of arylamines 9 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 10 Amines by reductive amination 11 Amines by Hoffman Rearrangement Have 1 less carbon atom 12 BASICITY OF AMINES NOTE: •pKa of conjugate acid • in water at 25 oC 13 REACTIONS OF AMINES Reactions with primary amines 14 Reactions with secondary amines 15 Reactions with carboxylic acid derivatives 16 Reactions with alkyl halides Nucleophilic substitution reaction Excess amine 17 The Hofmann elimination reaction Quaternary ammonium hydroxide formation 18 Different from Zaitsev’s product 19 Oxidation reactions Amines can be oxidized by hydrogen peroxide, peroxyacids, other common oxidizing agents 20