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THE CHEMISTRY OF AMINES

THE CHEMISTRY OF AMINES. AMINES. CONTENTS Structure and classification Nomenclature Physical properties Basic properties Preparation of amines Reactions of amines. H. H. R. R. R N :. R N :. R N :. +. R N R. H. R. R. R. STRUCTURE & CLASSIFICATION.

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THE CHEMISTRY OF AMINES

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  1. THE CHEMISTRYOF AMINES

  2. AMINES • CONTENTS • Structure and classification • Nomenclature • Physical properties • Basic properties • Preparation of amines • Reactions of amines

  3. H H R R R N: R N: R N: + R NR H R R R STRUCTURE & CLASSIFICATION Structure Contain the NH2 group Classification primary (1°) amines secondary (2°) amines tertiary (3°) amines quarternary(4°) ammonium salts Aliphaticmethylamine, ethylamine, dimethylamine AromaticNH2 group is attached directly to the benzene ring (phenylamine)

  4. NOMENCLATURE Common names: Derived by listing the names of the groups surrounding the nitrogen and adding the suffix amine Methyl amine Benzyl methyl amine Trimethyl amine Tetramethyl ammonium bromide IUPAC names: Derived by considering the amino group as a substituent and its position onthe chain is indicated by the lowest number. 3-Amino-5-methylhexane 5-Aminoheptanoic acid 3-Amino-2- butanol

  5. Aniline o-Nitroanilinep-Toluidinep-aminophenol p-nitro- N-ethylaniline

  6. Physical Properties of Alcohols Boiling Points of Amines • Because they possess a polar N-H bond, primary and secondary amines are capable of forming intermolecular hydrogen bonds among their molecules; therefore they have: Higher boiling points than alkanes but lower than alcohols. • All amines are capable of forming hydrogen bonds with water thus they are soluble in water. Solubility Of Amines

  7. Basicity of Amines • Because the nitrogen atom of 1 ◦, 2◦ and 3 ◦ amines has a lone pair of electrons; amines can be lone pair donors and proton acceptors from acids (i.e. they have basic properties) to form ammonium salt. • a proton acceptor • Base strength :depends on the availability of the lone pair and its ability to pick up protons • The greater the electron density on the N, the better it can pick up protons • This is affected by the degree of substitution ; electron donating groups on N atom increase the bacisity: eg. CH3-NH-CH3 > NH2-CH3 > NH3 2 ◦ 1 ◦ Ammonia H CH3 N: H

  8. While electron withdrawing substituents decrease basicityas the electron density on N is lowered effective. H C6H5 N: • Aliphatic amines are considerably more basic than aromatics amines. e.g.2: methylamine > ammonia > phenylamine

  9. Preparation of amines 1- Reduction of nitro compounds, nitriles, amides, and oximes

  10. 2- Alkylation of ammonia

  11. 3- Hoffman degradation of Amides

  12. Reactions of Amines

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