1. Diazonium salts synthesis benzenediazonium ion

2. Diazonium salts, reactions 1.Coupling to form azo dyes 2.Replacements a) -Br, -Cl, -CN b) -I c) -F d) -OH e) -H f) etc.

3. coupling to form azo dyes

4. Sandmeyer Ar-N 2 + + CuCl  Ar-Cl + N 2 Ar-N 2 + + CuBr  Ar-Br + N 2 Ar-N 2 + + CuCN  Ar-CN + N 2

5. Ar-N 2 + + KI  Ar-I + N 2 Ar-N 2 + + HBF 4  Ar-F + N 2 Ar-N 2 + + H 2 O, H +  Ar-OH + N 2 Ar-N 2 + + H 3 PO2  Ar-H + N 2

10. p-bromotoluene

12. 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!

13. m-bromotoluene

14. m-bromophenol

15. p-toluic acid

16. 1,2,3-tribromobenzene

17. 1,3,5-tribromobenzene

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

19. p-toluidine N—H stretch N—H bend

20. p-ethylaniline d c b a