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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: Dihydroxylation of an alkene can be carried out with H2O2 in HCO2H. In this reaction, transbut-2-ene affords (2R,3S)-butane-2,3-diol, whereas cis-but-2-ene affords a mixture of (2R,3R)-butane-2,3-diol and (2S,3S)-butane-2,3-diol. Does dihydroxylation by this method occur with syn or anti addition?

Question: It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions that you have learned in Chapters 8–12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: What carbonyl compound is formed when each alcohol is treated with HCrO4––Amberlyst A-26 resin?

a.

b.

c.

Question:Devise a synthesis of (3R,4S)-3,4-dichlorohexane from acetylene and any needed organic compounds or inorganic reagents.

Question: Draw the products formed when each diene is treated with O3 followed by CH3SCH3.

a.

b.

c.
See all solutions

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