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Diazonium salts synthesis. benzenediazonium ion. Diazonium salts, reactions Coupling to form azo dyes Replacements a) -Br, -Cl, -CN b) -I c) -F d) -OH e) -H f) etc. coupling to form azo dyes. Sandmeyer. Ar-N 2 + + CuCl  Ar-Cl + N 2

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Presentation Transcript
slide1

Diazonium salts

synthesis

benzenediazonium ion

slide2

Diazonium salts, reactions

  • Coupling to form azo dyes
  • Replacements
  • a) -Br, -Cl, -CN
  • b) -I
  • c) -F
  • d) -OH
  • e) -H
  • f) etc.
slide4

Sandmeyer

Ar-N2+ + CuCl  Ar-Cl + N2

Ar-N2+ + CuBr  Ar-Br + N2

Ar-N2+ + CuCN  Ar-CN + N2

slide5

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

slide12

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!

slide18

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)

slide19

p-toluidine

N—H

stretch

N—H bend