Reaction Name: Ozonolysis of 2-Methylbut-2-ene

Conversion: Alkene to

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General Form:

H 3C CH3 O
1. O3 O
2. (CH3 )2 S H 3C CH3
+
H 3C
H 3C

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Mechanism:

H3C
H 3C CH3
O H 3C H3C - +
- +
+ O O
H 3C
O O + O
O
CH
CH3
H 3C O O H3C
Important to choose the right direction
that electrons will flow.

H3C
O
O O

H 3C CH3

This product used to begin reaction 2. The

nucleophile will attack the weakest bond, the
peroxide bond (O-O).

H 3C -
H3C O CH3 O O CH3
O
O O + S CH3
O
CH3 CH3 + H3C + S
+ H CH3 CH3 O CH3
S
H 3C CH3 O CH3
H3C

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Notes: In the second step of the mechanism the electrons should flow in a way that would form
the most positive carbocation. In the step with dimethyl sulfide, the sulfide will attack the
oxygen with the weakest bond, typically the peroxide bond.

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Examples: Alkenes with ozone References: Lecture Notes