Skip to main content
Ch. 9 - Alkenes II: Oxidation and Reduction
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 9 - Alkenes II: Oxidation and ReductionProblem 29b
Chapter 8, Problem 29b

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3
(b)

Verified step by step guidance
1
Identify the alkene in the given structure. The double bond is located between the two carbon atoms connecting the isopropyl group and the cyclohexane ring.
Understand that ozonolysis involves the cleavage of the carbon-carbon double bond. Ozone (O₃) will react with the alkene to form an ozonide intermediate.
Recognize that the ozonide intermediate will be reduced by dimethyl sulfide (CH₃SCH₃) to form carbonyl compounds. Each carbon of the former double bond will become a carbonyl group.
Draw the products by replacing the double-bonded carbons with carbonyl groups. The isopropyl group will be attached to an aldehyde, and the cyclohexane ring will be attached to a ketone.
Ensure that the final structures are correctly drawn, showing an aldehyde and a ketone as the products of the ozonolysis reaction followed by reduction with dimethyl sulfide.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Ozonolysis

Ozonolysis is a reaction where ozone (O₃) cleaves alkenes to form carbonyl compounds. The process involves the formation of an ozonide intermediate, which is then reduced to yield aldehydes or ketones. This reaction is useful for breaking down complex alkenes into simpler, identifiable fragments.
Recommended video:
Guided course
06:30
General properties of ozonolysis.

Reductive Workup

Reductive workup in ozonolysis involves using a reducing agent, such as dimethyl sulfide (CH₃SCH₃), to convert the ozonide intermediate into stable carbonyl compounds. This step prevents the formation of carboxylic acids, ensuring that aldehydes are produced instead, which is crucial for maintaining the integrity of the original carbon skeleton.
Recommended video:
Guided course
03:16
Reductive Workup Mechanism:

Alkene Structure

Understanding the structure of the alkene is essential for predicting the products of ozonolysis. The alkene in the image is a cyclohexene with an isopropyl group attached, indicating that ozonolysis will cleave the double bond, resulting in two carbonyl compounds: an aldehyde from the isopropyl group and a ketone from the cyclohexene ring.
Recommended video:
1:59
Alkene Metathesis Concept 5
Related Practice
Textbook Question

Despite it being equally favorable, opening of the epoxide does not happen in the absence of an acid catalyst. How does acid make the reaction faster? Demonstrate this concept by directly comparing the reaction coordinate diagram for both situations A and B.

2
views
Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(c)

Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(a)

Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(d)

3
views
Textbook Question

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.

(a)

Textbook Question

In Assessment 9.26, what is the relationship between the enantiomers of compound A and the enantiomers of compound B?

1
views