Aromatic Synthetic Routes

Question 1

Benzene to Chlorobenzene

Answer 1

Halogenation
Cl2 + AlCl3 catalyst

Question 2

Benzene to Alkylbenzene

Answer 2

Friedel-Crafts Alkylation
R-Cl + AlCl3 catalyst

Question 3

Benzene to Bromobenzene

Answer 3

Halogenation
Br2 + FeBr3 catalyst

Question 4

Benzene to Nitrobenzene

Answer 4

Nitration
Conc H2SO4 catalyst + Conc HNO3 (aqua regia)

Question 5

Benzene to Phenylketone

Answer 5

Friedel-Crafts Acylation
Acyl Chloride + AlCl3 catalyst

Question 6

Phenol to 2,4,6 Tribromophenol

Answer 6

Halogenation
3Br2

Question 7

Phenol to Phenylester

Answer 7

Condensation
Acyl Chloride or Acid Anhydride or Carboxylic Acid

Question 8

Phenol to 2-nitrophenol

Answer 8

Nitration
Dilute HNO3

Question 9

Benzoic acid to Benzoylchloride

Answer 9

Substitution
SOCl2

Question 10

Benzonitrile to Benzoic Acid

Answer 10

Hydrolysis
H2O + HCl catalyst

Question 11

Benzaldehyde to Benzoic Acid

Answer 11

Oxidation
Acidified Potassium Dichromate
reflux

Question 12

Benzoylchloride to Benzoic Acid

Answer 12

Substitution
H2O

Question 13

Nitobenzene to Phenylamine

Answer 13

Reduction
Sn, conc HCl (reducing agent [H])

Question 14

Electron withdrawing

Answer 14

pulls electron density from delocalised ring system
directs route to the 3 position

Question 15

Electron Donating

Answer 15

Adds electron density to the delocalised ring system
directs routes to the 2,4 position