Aromatic routes

Question 1

Benzene —> Alkyl benzene

Answer 1

CH3Cl/ AlCl3
Alkylation
ELECTROPHILIC SUBSTITUTION

Question 2

Benzene —> Nitrobenzene

Answer 2

conc H2SO4 & conc HNO3
NO2+ formed in situ
ELECTROPHILIC SUBSTITUTION

Question 3

Nitrobenzene —> Phenylamine

Answer 3

1. Sn/ conc HCl
2. Excess NaOH (aq) added to turn salt into amine

Question 4

Phenylamine —> Bromophenylamine

Answer 4

Br2 (aq)
(forms multi-substituted product)

Question 5

Benzene —> Bromobenzene

Answer 5

Br2/ Halogen carrier (e.g. AlBr3 or FeBr3)
ELECTROPHILIC SUBSTITUTION

Question 6

Benzene —> Chlorobenzene

Answer 6

Cl2/ Halogen carrier (e.g. AlCl3 or FeCl3)
ELECTROPHILIC SUBSTITUTION

Question 7

Benzene —> Phenylketone

Answer 7

Acyl Chloride/ AlCl3.
(e.g. +ethanoyl chloride forms phenylethanone)

Question 8

Phenylketone —> Phenyl alcohol

Answer 8

NaBH4

REDUCTION

Question 9

Phenol —> Bromophenol

Answer 9

Br2 (aq)
ELECTROPHILIC SUBSTITUTION

Question 10

Phenol —> Sodium Phenoxide

Answer 10

NaOH (aq)
Phenol acts as a weak acid, NEUTRALISATION

Question 11

Phenol —> Nitrophenol

Answer 11

Dilute HNO3 (aq)
Produces mixture of 2 isomers. (NO2 at posititions 2 and 4)