Organic Chemistry II Problem Set 3 Reaction of Substituted Benzene

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Organic Chemistry II

Problem Set 3
Reaction of Substituted Benzene
Write products for these reactions. If no reaction occurs, write N.R.

1. HNO3
anisole
H2SO 4

O
2. Br2
O C
FeBr3

O
3. Br2
H3C C NH
FeBr3

4. Cl

CH3 C O
Cl
AlCl3

5. i-Pr-Cl
aniline
AlCl3

O t-Bu-Cl
6. H3C O C
AlCl3

7. HCl
CH CH CH3

8. EtCl NBS KOH(alc) cold dilute


AlCl3 heat KMnO 4

Cl
9. a. excess KMnO4 / OH- reflux
CH3 CH CH3
toluene
AlCl3 b. H+
10.
Br2

Light
cumene
Cl
11.
CH3 CH2 C O H2
AlCl3 Pd

12. a. acetyl chloride / AlCl3


t-butylbenzene
b. NaBH 4 in EtOH / H 2O

CH2Cl2
13.
AlCl3
excess

14. O
Zn(Hg)
CH2 CH2 C AlCl3 HCl
Cl

15. N2H4 / OH-


acetophenone
heat

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