Diazonium salts synthesis - PowerPoint PPT Presentation

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Diazonium salts synthesis

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  1. Diazonium salts synthesis benzenediazonium ion

  2. Diazonium salts, reactions • Coupling to form azo dyes • Replacements • a) -Br, -Cl, -CN • b) -I • c) -F • d) -OH • e) -H • f) etc.

  3. coupling to form azo dyes

  4. Sandmeyer Ar-N2+ + CuCl  Ar-Cl + N2 Ar-N2+ + CuBr  Ar-Br + N2 Ar-N2+ + CuCN  Ar-CN + N2

  5. Ar-N2+ + KI  Ar-I + N2 Ar-N2+ + HBF4 Ar-F + N2 Ar-N2+ + H2O, H+ Ar-OH + N2 Ar-N2+ + H3PO2  Ar-H + N2

  6. p-bromotoluene

  7. In syntheses, you may no longer assume that you can separate a pure para isomer from an ortho/para mixture. Either look up the physical properties of the compounds or rely on experience gained in the homework as to which mixtures are separable and which ones are not!

  8. m-bromotoluene

  9. m-bromophenol

  10. p-toluic acid

  11. 1,2,3-tribromobenzene

  12. 1,3,5-tribromobenzene

  13. Spectroscopy of amines Infrared: N—H stretch 3200 – 3500 cm-1 1o often two bands 2o one band 3o no bands N—H bend 1o strong bands 650-900 cm-1(broad) and 1560-1650 cm-1 nmr: N—H 1-5 ppm (often broad and low)

  14. p-toluidine N—H stretch N—H bend

  15. p-ethylaniline d c b a