TAILIEUCHUNG - Chapter 13: AMINES-DIAZONIUM SALTS

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: ptsnam@ 1 .Chapter 13: AMINES-DIAZONIUM SALTS 2 .NOMENCLATURE OF | 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: ptsnam@ Chapter 13: AMINES-DIAZONIUM SALTS NOMENCLATURE OF AMINES Common names: alkyl + amine IUPAC names: alkan + amine Substituents are listed in alphabetical order, regardless of whether they are attached to the nitrogen or the hydrocarbon PREPARATIONS OF AMINES Alkylation of ammonia Gabriel synthesis of primary amines Amines by reduction Preparation of arylamines It is possible to selectively reduce just 1 of 2 nitro groups using S2- H2 /Pd, Fe/HCl will reduce both nitro groups 1:1 molar ratio Amines by reductive amination Amines by Hoffman Rearrangement Have 1 less carbon atom BASICITY OF AMINES NOTE: pKa of conjugate acid in water at 25 oC REACTIONS OF AMINES Reactions with primary amines Reactions with secondary amines Reactions with carboxylic acid derivatives Reactions with alkyl halides Nucleophilic substitution reaction Excess amine The Hofmann elimination reaction Quaternary ammonium hydroxide formation Different from Zaitsev’s product Oxidation reactions Amines can be oxidized by hydrogen peroxide, peroxyacids, other common oxidizing agents Reaction of primary amines with HNO2 Stable NOT stable HNO2 is unstable, aqueous NaNO2 / acid should be used Mechanism: Alkyl diazonium salt is NOT stable REACTIONS OF DIAZONIUM SALTS Sandmeyer reactions KCl, KBr can NOT be used in place of CuCl, CuBr This Cl is from CuCl Schiemann reaction Preparation of phenol from diazonium salt Reductive deaminations Anhydrous C2H5OH, NaBH4 can be used in place of H3PO2 Azo coupling reactions Substitution will occur at 1 ortho position if the para is blocked Electrophilic aromatic substitution Electron-donating group DESIGNING A SYNTHESIS

• Trung học phổ thông
• organic chemistry
• hóa hữu cơ
• công nghệ hóa học
• Chemical Engineering
• amines
• diazonium salts
• In this workbook
• experiments are elaborated using small scale glassware and equipments from a Small Lab Kit
• developed at the Department of Chemistry
• Faculty of Science
• Chulalongkorn University in Thailand
• This Small Lab Kit was created as a result of the research project entitled “Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” sponsored by Thai Research Fund (RDG 3 07 2543)
• One of the outcomes of this project is the organic laboratory book entitled “Organic Chemistry Laboratory Based on Chemical Safety and Pollution Minimization” written in Thai by professors from 7 universities in this project
• They compiled
• adjusted and tested the experiments taken from several traditional organic chemistry laboratory books using the prototype of Small Lab Kit
• Currently
• some selected experiments from this Thai organic chemistry laboratory text have further been modified
• rewritten and edited in English as appeared in this workbook
• Some experiments ar
• Ebook Organic chemistry
• Nucleophilic substitution
• Determining organic structures
• nucleophilic addition
• Organic structures
• Electrophilic aromatic substitution
• Principles of organic chemistry
• Methods of organic chemistry
• The methane series
• The acetylene series
• Polybasic acids
• High school
• University entrance exam
• Teaching organic chemistry
• Organic chemistry exam question
• Interdisciplinary science
• Advanced practical organic chemistry
• Functional groups
• Organic synthesis reagents
• The structure
• Reactions of organic names
• Fundamentals of organic chemistry
• Carbonyl alpha substitution reactions
• Condensation reactions
• Structure determination
• The organic chemistry
• Organic chemistry principles in context
• Starch to the principles
• The structures of organic molecules
• Mass spectrometers
• Infrared spectrometers
• Nuclear magnetic resonance spectrometers
• Modern physical organic chemistry
• Strain and stability
• Covalent binding forces
• Electronic organic materials
• Thermal pericyclic reactions
• The study of organic chemistry
• Stereochemistry and resonance
• Identification of organic compounds
• Elimination reactions
• Electrophilic addition reactions
• Electron delocalization
• Organic compounds
• Cyclic hydrocarbons
• Aromatic alcohols
• Aromatic compounds containing
• Inorganic chemistry
• A guidebook to mechanism in organic chemistry
• Aromatic systems
• Linear free energy relationships
• Symmetry controlled reactions
• Fatty acid catabolism
• The chemistry of the carbonyl group
• The industrial road toward increasing efficiency
• Lecture Organic chemistry
• Hóa học hữu cơ
• Bài giảng Hóa học hữu cơ
• Chemistry of benzene
• Derivatives of benzene
• Summary of Organic Chemistry Dotoral Thesis
• Organic Chemistry Dotoral Thesis
• Natural Products Chemistry
• Biological evaluation
• Chemistry of natural compounds
• Ideas in chemistry
• Molecular sciences
• Synthetic chemistry
• Innovative processes in organic chemistry
• Predictive tools
• Organic chemical reactions
• Electronic Structure
• Electronic configurations of atoms
• Electronic configurations
• Wave properties of electrons
• Wave interactions
• Stereochemistry of alkanes
• Alkane conformations
• Chemical reactions
• Chlorination of Methane
• Chiral carbons
• Nonmobile conformers
• Alkyl Halides