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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: How many rings and 蟺 bonds are contained in compounds A鈥揅? Draw one possible structure for each compound.

a. Compound A has molecular formula C5H8 and is hydrogenated to a compound having molecular formula C5H10.

b. Compound B has molecular formula C10H16 and is hydrogenated to a compound having molecular formula C10H18 .

c. Compound C has molecular formula C8H8 and is hydrogenated to a compound having molecular formula C8H16.

Question: What alkane is formed when each alkene is treated with H2 and a Pd catalyst?

a.

b.

c.

Question: A chiral alkyne A with molecular formula C6H10 is reduced with and Lindlar catalyst to B having the R configuration at its stereogeniccentre. What are the structures of A and B?

Question: In the Cr6+oxidation of cyclohexanols, it is generally true that sterically hindered alcohols react faster than unhindered alcohols. Which of the following alcohols should be oxidized more rapidly?

Question: Draw the products formed in each oxidative cleavage.

a.

b.

c.

d.
See all solutions

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