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Amines - classification

Amines - classification. 1 o. 2 o. quaternary ammonium salts. 3 o. Nomenclature. To name aliphatic amines, name the alkyl groups bonded to the amine nitrogen and then add the suffix “ amine ”:. C 2 H 5 NHCH 3. (CH 3 ) 3 CNH 2. ethylmethylamine. t -butylamine.

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Amines - classification

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  1. Amines - classification 1o 2o quaternary ammonium salts 3o

  2. Nomenclature To name aliphatic amines, name the alkyl groups bonded to the amine nitrogen and then add the suffix “amine”: C2H5NHCH3 (CH3)3CNH2 ethylmethylamine t-butylamine Systematic nomenclature adds the suffix to the name of the hydrocarbon: CH3CH2NH2 C2H5NHCH3 ethanamine N-methylethanamine

  3. Nomenclature In the IUPAC system, the -NH2 group is called the amino group. The prefix “amino” (or “methylamino”, “diethylamino” etc.) is therefore used in naming complex molecules. 4-aminobutanoic acid -aminobutyric acid H2NCH2CH2CH2CO2H H2NCH2CH2OH 2-aminoethanol ethanolamine 2-methylaminoheptane

  4. Nomenclature m-nitroaniline 3-nitrobenzenamine N-ethyl-N-methylaniline N-ethyl-N-methylbenzenamine

  5. Nomenclature Salts of amines are named by replacing the suffix amineby ammonium:- ethylammonium sulfate trimethylammonium nitrate anilinium chloride

  6. Physical Properties Tertiary amines, having no N-H bonds, cannot form hydrogen bonds (N-H-------N). 1o and 2o amines can! Their intermolecular association by hydrogen bonding reduces their volatility relative to hydrocarbons of similar molecular weight. Amines having less than six carbon atoms show an appreciable water solubility.

  7. Preparation - alkylation

  8. Preparation - reduction of nitro compounds 1º amine

  9. Preparation - reductive amination amphetamine

  10. Preparation - reduction of nitriles

  11. Preparation - Hofmann degradation phentermine - an appetite suppressant

  12. Hofmann degradation

  13. Reactions - basicity weaker base stronger base

  14. Reactions - basicity Kb: CH3NH2 = 4.75x10-4, NH3 = 1.78x10-5, C6H5NH2 = 4.26x10-10

  15. Reactions - basicity Kb: CH3NH2 = 4.75x10-4, NH3 = 1.78x10-5

  16. Reactions - basicity

  17. Reactions - basicity

  18. Substituent effects Substituents attached to the aromatic ring which are electron attracting reduce the basicity of amines. Electron-repelling substituents increase amine basicity.

  19. Action of nitrous acid + 1. NaNO /H 2 RNH ROH 2 D 2. H O/ 2

  20. Aromatic diazonium salts

  21. Sandmeyer reaction

  22. Gattermann reaction

  23. Aromatic diazonium salts

  24. Aromatic diazonium salts Synthesis of phenols Substitution by H

  25. Synthesis of the three bromotoluenes oops

  26. Synthesis of the bromotoluenes

  27. Synthesis of m-bromotoluene

  28. Coupling Reactions of Diazonium Compounds An electrophilic attack...... p-(dimethylamino)azobenzene

  29. congo red

  30. Preparation of substituted amides

  31. Nomenclature of Substituted Amides

  32. Sulfanilic acid ? mp > 280-300o OH- - soluble H+ - insoluble dipolar ion - a zwitterion “zwitter” - hermaphrodite

  33. Sulfa drugs sulfanilimide

  34. Spectroscopic Properties N-H - stretching 3300 - 3500 cm-1 1o amines show 2 high intensity peaks NMR - the amino H gives a peak which can be found almost any where in the spectrum (similar to the -O-H proton).

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