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Chapter 12: PROBLEM 12.49 (page 490)

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

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

Step by step solution

01

Alkene and alkyne

An alkene has a double bond, and an alkyne has a triple bond. Therefore, the physical and chemical properties of alkene and alkyne are different from each other.

02

Ozonolysis of alkene

An alkene can have more substitution. Therefore, an alkene can form an aldehyde and a ketone both.

If there is a substituted alkene, the ketone will be the product of ozonolysis. If there is an unsubstituted alkene, the ketone and aldehyde will be the products.

03

Explanation

a. The given compounds are one ketone and one molecule of aldehyde. Therefore, the alkene is an unsubstituted alkene from the aldehyde end.

The reaction is shown as:

Ozonolysis of a

b. The given compounds are ketones. Therefore, the alkene is a substituted alkene.

The reaction is shown as:

Ozonolysis of b

c. The given compounds are aldehydes. Therefore, the alkene is a less substituted alkene.

The reaction is shown as:

Ozonolysis of c

d. The given compounds are ketone and two moles of aldehydes. Therefore, the alkene is a less substituted alkene.

The reaction is shown as:

Ozonolysis of d

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