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Chapter 8: 8-31 (page 262)

Propose a curved-arrow mechanism to show how ozone (O3) reacts

with a carbon鈥揷arbon double bond to form a molozonide, the first intermediate

in ozonolysis.

Short Answer

Expert verified

Curved-arrow mechanism:

Step by step solution

01

Ozonolysis

Christian Fredrich Schonbein was the one who did ozonolysis firstly further Carl Dietrich Harries attributed in the ozonolysis of alkene therefore; this reaction was also named as Harries ozonolysis. Ozonolysis is a type of oxidation reaction. With the help of ozone (O3) unsaturated hydrocarbons such as alkene or alkyne can be directly converted into aldehyde or ketone.

Ozonolysis of alkene can be shown as:

Ozonolysis of alkene

02

Molozonide

Molozonide is an unstable intermediate formed in the first step of ozonloysis. In the mechanism to form molozonide, 1 mole of ozone () will react with the alkene. It is a concerted (in which formation of bond and breaking of bond takes place simultaneously) cycloaddition reaction.

03

Curved-arrow mechanism

Curved -arrow mechanism to form molozonide with the help of ozone and alkene having carbon atoms is as shown below:

Formation of Molozonide

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Most popular questions from this chapter

Question:The addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as a sole product. Use resonance structures of the carbocation intermediate to explain why none of the alternate regioisomers isformed.

Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

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Question: Which of the following alcohols could notbe made selectively by hydroboration鈥搊xidation of an alkene? Explain.

When a single alkene monomer, such as ethylene, is polymerized, the product is a homopolymer. If a mixture of two alkene monomers is polymerized, however, a copolymer often results. The following structure represents a segment of a copolymer called Saran. What two monomers were copolymerized to make Saran?

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution:


a.CH3CH2CO2H+CO2
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