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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: Explain why only one C=C of geraniol is epoxidized with the Sharpless reagent.

Question: Explain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene.

Question: Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by 鈥� OH (in H2O ). Explain how these reactions illustrate that anti-dihydroxylation is stereospecific.

Question: What alkene is needed to synthesize each 1,2-diol using [1] followed by NAHSO3 in H2O ; or [2] CH3CO3H followed by -OH in H2O ?

a.

b.

c.

Question: Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent:

(a) mCPBA; (b) Br2 , H2O followed by base? Explain these results.
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