Advices For Studying Organic Chemistry

ketone.

CH 3 CH 2 C

CH 3

CH 2

1. KMnO 4 , OH−, heat


2. H 3 O+

CH 3 CH 2 C O O +

CH 3

O + C H 2 O

4. The oxidative cleavage of alkenes has been used to establish the location of the

8.11A

pontaneously to form ozonides.

double bond in an alkene chain of ring.

OZONOLYSIS OF ALKENES

1. Ozone reacts vigorously with alkenes to form unstable initial ozonides
   (molozonides) which rearrange s

1. The rearrangement is thought to go through dissociation of the initial ozonide
   into reactive fragments that recombine to give the ozonide.

A Mechanism for the Reaction

Ozonide Formation from an Alkene

C

O

C

− O+O

+

Ozone adds to the alkene Initial ozonide

to form an initial ozonide.

CC CC

Th fragm

O

e initial ozonide ents.

O

O

−O O O

O

C

O

C C

O C

− O+O O

The fragments recombine to form the ozonide. Ozonide

(^)

2. Ozonides are very unstable compounds and low molecular weight ononides often
   explode violently.