Organic conversion

Benzene to acetophenone

1 step: Friedel-Crafts acylation

Class 12, Chapter 8 Aldehydes, Ketones and Carboxylic Acids

Alternative routes (3)

Benzene → Toluene → Benzoic acid → Benzoyl chloride → Acetophenone
1. Benzene to toluene: CH₃Cl, anhydrous AlCl₃.
2. Toluene to benzoic acid: KMnO₄, KOH, heat; then H₃O⁺.
3. Benzoic acid to benzoyl chloride: SOCl₂.
4. Benzoyl chloride to acetophenone: (CH₃)₂Cd.
Benzene → Ethylbenzene → Benzoic acid → Benzoyl chloride → Acetophenone
1. Benzene to ethylbenzene: CH₃CH₂Cl, anhydrous AlCl₃.
2. Ethylbenzene to benzoic acid: KMnO₄, KOH, heat; then H₃O⁺.
3. Benzoic acid to benzoyl chloride: SOCl₂.
4. Benzoyl chloride to acetophenone: (CH₃)₂Cd.
Benzene → Benzaldehyde → Benzoic acid → Benzoyl chloride → Acetophenone
1. Benzene to benzaldehyde: CO + HCl, anhydrous AlCl₃ / CuCl.
2. Benzaldehyde to benzoic acid: KMnO₄, KOH, heat; then H₃O⁺.
3. Benzoic acid to benzoyl chloride: SOCl₂.
4. Benzoyl chloride to acetophenone: (CH₃)₂Cd.

Why these reagents

Reagent and reason, step by step

Step 1: Benzene to acetophenone: CH₃COCl, anhydrous AlCl₃ Friedel-Crafts acylation: the acyl group deactivates the ring, so it stops at one substitution.

Questions

How many steps does it take to convert benzene to acetophenone?

1 step: Benzene, then acetophenone.

Which named reaction is used to convert benzene to acetophenone?

Friedel-Crafts acylation. Benzene reacts with an acyl chloride or anhydride in the presence of anhydrous AlCl3 to give an aromatic ketone.

What is the reagent for step 1 of benzene to acetophenone?

Benzene to acetophenone: CH₃COCl, anhydrous AlCl₃. Friedel-Crafts acylation: the acyl group deactivates the ring, so it stops at one substitution.