Mesitylene

Acetone on distillation with conc. H2SO4 forms?

Acetone, also known as propanone, is a commonly used organic solvent. When it undergoes distillation with concentrated sulfuric acid (H2SO4), it can produce a variety of compounds. The main products obtained from this reaction are phorone, acrolein, mesitylene, and mesityl oxide.

The products formed:

1. Phorone:
- Phorone is a cyclic compound that contains a conjugated system of double bonds.
- It is formed by the condensation reaction of two molecules of acetone in the presence of concentrated sulfuric acid.
- The reaction proceeds through an aldol condensation mechanism, where the α-carbon of one acetone molecule attacks the carbonyl carbon of another acetone molecule.
- The resulting intermediate undergoes dehydration to form phorone.

2. Acrolein:
- Acrolein is an unsaturated aldehyde with the chemical formula CH2=CHCHO.
- It is formed by the dehydrogenation of acetone in the presence of concentrated sulfuric acid.
- The reaction proceeds through the removal of two hydrogen atoms from acetone, resulting in the formation of a double bond between the α-carbon and the carbonyl carbon.

3. Mesitylene:
- Mesitylene is a hydrocarbon with the chemical formula C6H3(CH3)3.
- It is formed by the condensation and rearrangement reactions of acetone in the presence of concentrated sulfuric acid.
- The reaction proceeds through the dimerization of acetone, followed by a rearrangement of the resulting intermediate to form mesitylene.

4. Mesityl Oxide:
- Mesityl oxide is an α,β-unsaturated ketone with the chemical formula C6H10O.
- It is formed by the oxidation of mesitylene, which is produced during the distillation of acetone with concentrated sulfuric acid.
- The oxidation is typically carried out using an oxidizing agent such as potassium permanganate (KMnO4) or chromic acid (H2CrO4).

Summary:
- Acetone, when distilled with concentrated sulfuric acid, can form phorone, acrolein, mesitylene, and mesityl oxide.
- Phorone is formed through aldol condensation and dehydration of acetone.
- Acrolein is formed through dehydrogenation of acetone.
- Mesitylene is formed through condensation and rearrangement reactions of acetone.
- Mesityl oxide is formed through the oxidation of mesitylene.