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Chapter 12: PROBLEM 12.30 (page 487)

Question: Draw the products formed when the following diene is treated with O3followed by H3CSCH3 .

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01

Oxidative cleavage of alkenes using  O3/CH3SCH3

The oxidative cleavage of alkenes, also known as ozonolysis, is done by treating them with ozone to form an unstable intermediate called molozonide.

This intermediate is then converted into ketone and aldehyde by treating it with dimethyl sulfide,CH3SCH3 .

The general reaction scheme is given below:

Oxidation cleavage of alkenes

02

Determination of product 

The skeletal structure of the given compound is as follows:

Skeletal structure

When this compound reacts with O3/ H3CSCH3 , the product that is formed is given below:

Reductive oxidation withO3/ H3CSCH3

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Most popular questions from this chapter

Question: Draw the organic products formed in each reaction.

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d.

Question: In the Cr6+oxidation of cyclohexanols, it is generally true that sterically hindered alcohols react faster than unhindered alcohols. Which of the following alcohols should be oxidized more rapidly?

Question: Draw the organic products in each of the following reactions.

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Question: Draw the products formed when each alkyne is treated with O3 followed by H2O .

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Question: Draw a stepwise mechanism for the following reaction.
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