Arenes

Question 1

Benzene -> Methylbenzene + HCl

Answer 1

R-Cl, AlCl3 (anhydrous)

Question 2

Benzene -> Bromobenzene + HBr

Answer 2

Br2, FeBr3 (anhydrous)

Question 3

Requirement for E Sub of Arenes

Answer 3

Lewis acid, electron pair acceptor reacts with halogen/alkyl/acyl to form positively charged ephile. (delta plus not enough due to ring resonance)

Question 4

Benzene -> Nitrobenzene + H2O

Answer 4

Conc. HNO3, Conc. H2SO4, 60°C

Question 5

Benzene + acyl chloride = ?

Answer 5

Anhydrous AlCl3 catalyst

Removal of Chloride to form HCl, the rest of the reagent connects to the ring.

Question 6

Methylbenzene -> nitromethylbenzene

Answer 6

Conc. HNO3, Conc. H2SO4, 30°C

Question 7

Acidic oxidation of Methylbenzene

Answer 7

KMNO4, H2SO4 (aq), HEAT
Side chain (alkyl, alcohol, carbonyl) becomes C. Acid + form H2O
If side chain has more than one carbon, balance w CO2 pdt

Question 8

Alkaline oxidation of Methylbenzene

Answer 8

KMNO4, NaOH (aq), HEAT
Side chain (alkyl, alcohol, carbonyl) becomes COO- + form H2O
If side chain has more than one carbon, balance w Na2CO3 pdt

Question 9

Condition for side chain oxidation

Answer 9

Side chain must contain -H / -OH / =O directly bonded to the C bonded to ring.