Benzene RXN

Question 1

Add Br

Answer 1

Br2, FeBr3.

Br+, Fe-Br4

Question 2

Add Cl

Answer 2

Cl2, AlCl3

Question 3

Add I

Answer 3

I2, CuCl2

Question 4

Nitrate

Answer 4

Adds NO2.
HNO3, H2SO4.

Nitric takes H, loses H2O. NO2+ intermediate.

Question 5

Add NH2

Answer 5

1. HNO3, H2SO4.

2. SnCl2, H2O

Question 6

Diazonium Ion

Answer 6

1. HNO3, H2SO4
2. SnCl2, H2O
3. NaNO2, HCl

Question 7

Diazonium to X

Answer 7

CuX

Question 8

Diazonium to D

Answer 8

D2PO3

Question 9

Diazonium to H

Answer 9

H2PO3

Question 10

Diazonium to OH

Answer 10

Cu2O, H2O

Question 11

Diazonium to CN

Answer 11

CuCN

Question 12

Friedel-Crafts Alkylation

Answer 12

RCl, AlCl3

No EWG or free amino on ring. Carbocation intermediate.

Question 13

Friedel-Crafts Acylation

Answer 13

RCOCl, AlCl3.

No EWG or free amino on ring.

Question 14

Removing carbonyls

Answer 14

H2, Pd/C

Or Zn(Hg), HCl

Question 15

Form Carboxylic Acid

Answer 15

KMnO4, to any place with an H.

Question 16

Halogen to NH2

Answer 16

NaNH2, NH3

At or adjacent LG. Needs adjacent proton. Benzyne intermediate can do Diels-Alder.

Question 17

OR- for Halogen

Answer 17

OR-, ROH.

NES, needs EWG in O/P.

Question 18

Sulfation

Answer 18

Adds SO3H

SO3, H2SO4