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Chapter 12: PROBLEM 12.21 (page 476)

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

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Oxidative cleavage of alkenes

The oxidative cleavage of alkenes is also known as ozonolysis. The double bonds of alkene are cleaved to form aldehydes or ketone.The general reaction scheme is given below:

Oxidation cleavage of alkenes

02

Ozonolysis using  O3 / CH3SCH3

The ozone reacts with the alkene to form an unstable intermediate that is known as molozonide. This intermediate is converted to carbonyl compounds using the reagent dimethyl sulphide.

03

Determining the products

The given compounds are treated with ozone and dimethyl sulohide to give the following products:

a.

Ozonolysis of alkene

b.

Ozonolysis of alkene

c.

Ozonolysis of alkene

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Most popular questions from this chapter

Question: Draw the organic products formed when allylic alcohol A is treated with each reagent.

a. H2 +Pd-c

b. mCPBA

c. PCC

d. CrO3 ,H2SO4, H2O

e.(CH3)3COOH , Ti [OCH(CH3)3]4 (+) -DET

f.(CH3)3COOH , Ti [OCH(CH3)3]4 (-) -DET

g. [1] PBr3,[2] LiAlH4 ,[3] H2O

h. HCrO4- –Amberlyst A-26 resin

Question: What is the structure of cis-jasmone, a natural product isolated from jasmine flowers, formed by the treatment of alkyne A with H2in the presence of the Lindlar catalyst?

Question: Which alkyne has the smaller Heat of hydrogenation HC≡CCH2CH2CH3orCH3C≡CCH2CH3 ? Explain your choice.

Question: Draw the organic products formed in each reaction.

a.

b.

c.

d.

Question: Sodium hypochlorite (NaOCl, the oxidant in household bleach) in aqueous CH3COOH is also touted as a “green” oxidizing agent. For example, oxidation of (CH3)2CHOH with NaOCl forms along with NaCl and H2O. (a) What advantages and/or disadvantages does this method have over oxidation with HCrO4––Amberlyst A-26 resin? (b) What advantages and/or disadvantages does this method have over oxidation with CrO3, H2SO4,H2O.
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