Ozonolysis Mechanism (Exercise in Arrow Pushing):

The general reaction is as follows:

1) O3 R O
R + R'
R' 2) Zn/ H 2O O

Notice both of σ and π bonds of the alkene are broken, to produce two new
carbon oxygen double bonds.
A mechanism is presented below. Try to follow the motion of the electrons
through each step of this mechanism. Remember each arrow indicates the
motion of two electrons, either a) from a lone pair to a bond, b) from a bond
to a lone pair, c) from a bond to another bond. Try to find examples of each
of these types of electron motion in the following mechanism.
O

O O O O
O O O O
R H

R H R H

H R' R' R'

H H
Ozonide
These pieces flip
around

OH

OH H
O
OH O
O O H 2O O R'
H H
R R
H
R
O R' H O R' O
H
H

R O
+ R' H2O2
O +

The purpose of the zinc is to reduce the hydrogen peroxide which is generated in the hydrolysis
of the ozonide intermediate. (see pp 245-247 Carey).