Numford
Name reaction

Ozonolysis

Ozone adds to an alkene to form an ozonide, which is cleaved by zinc and water to give aldehydes or ketones.

Class 11, Chapter 9 Hydrocarbons

  1. But-2-eneCH₃CH=CHCH₃Alkene
  2. Step 1

    (i) O₃ (ii) Zn, H₂O

    Ozonolysis
    i

    Ozonolysis splits the double bond into two molecules of ethanal.

    OH
    EthanalCH₃CHOAldehyde

Reagents: (i) O₃ (ii) Zn, H₂O

Mechanism

How it works

  1. Ozone adds across the C=C to give a molozonide, then an ozonide.
  2. Zn and water cleave the ozonide.
  3. Two carbonyl compounds form, and zinc prevents over-oxidation to acids.
Used to prepare

What it makes

Aldehydes and ketones; also locates a double bond.

Limitations

Where it fails

Zinc is needed to keep aldehydes from being oxidised by hydrogen peroxide.

Which chapter

Class 11, Chapter 9 Hydrocarbons

Questions

Ozonolysis: quick answers

What is the role of zinc dust?

It reacts with H2O2 formed, so aldehydes are not oxidised to acids.

What does but-2-ene give?

Two molecules of ethanal.

What does propene give?

Ethanal and methanal.

Plan an organic conversion