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-N CuCl  Ar-Cl N2
Ar-N CuBr  Ar-Br N2
Ar-N CuCN  Ar-CN N2

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

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 – 3500 cm-1
1o often two bands o one band o no bands
N—H bend
1o strong bands cm-1(broad) and 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