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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 all alkenes that react with one equivalent of H2 in the presence of a palladium catalyst to form each alkane. Consider constitutional isomers only

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Question: What alkane is formed when each alkene is treated with H2 and a Pd catalyst?

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Question: Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3+H2O. Explain how these reactions illustrate that syndihydroxylation is stereospecific.

Question: Draw the product of each asymmetric epoxidation reaction.
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