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Chapter 12: PROBLEM 12.19 (page 475)

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

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Oxidative cleavage

The term oxidative cleavage itself defines the reaction.

Oxidative-addition of oxygen, and cleavage- breaking of carbon-carbon double bond.

In oxidative cleavage, the 蟽 and 蟺bond of alkenes is cleaved, and two C=O (carbonyl bonds are formed).

02

Ozonolysis

Oxidative cleavage using ozone as an oxidizing agent is termed ozonolysis. It is a two-step mechanism where ozonide is formed in the first step, which is converted to carbonyl group using reagents Zn (in water)

03

Oxidative cleavage of compound

Depending on the R groups, aldehyde or ketone products are obtained.

a.

Oxidative cleavage- one aldehyde and one ketone product

b.

Oxidative cleavage- two aldehyde products

c.

Oxidative cleavage- two carbonyl bond formation

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Most popular questions from this chapter

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: 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鈥�12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: What alkene or alkyne yields each set of products after oxidative cleavage with ozone?

a.

b.

c.

d.

Question: Identify the starting material in each reaction.

a.

b.

Question: Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6-dimethyloctane when treated with H2and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C=O, CH2=O, CH2(CHO)2and CH3COCHO. Ozonolysis of myrcene yields (CH3)2CO, CH2=O(two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.
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