O-Chem : Exam 1

Benzoic Acid

phenol

toluene

Aniline

Benzaldehyde

Styrene

Br2, FeBr3 (or ALBr3)

Bromination

Cl2, FeCl3 (or AlCl3)

Chlorination

I2, CuCl2

Iodination

H2SO4, HNO3

Nitration (NO2)

H2SO4, SO3

Sulfonation (SO3H)

R-x, AlX3 X= Cl, Br, I

alkylation (Friedel Crafts)

acid chloride, AlCl3

acylation (Friedel Crafts)

Zn(Hg), HCL

Clemmensen Reduction

N2H4, KOH, Heat

Wolff-Kishner Reduction

To make anilines (NH2)

1. HNO3, H2SO4

2. Sn, HCL

To make benzoic acids (CO2H)

1. CH3-Br, ALBr3

2. KMnO4

Electron Donating in order

1. NR2

2. OH

3. OR

4. R

5. Ph

Electron Withdrawing in order

1. X

2. COG

3. SO3H

4. C=N

5. No2