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Ch. 9 - Alkenes 2: Oxidation and Reduction
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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Tutti i libri di testoMullins 1st EditionCh. 9 - Alkenes 2: Oxidation and ReductionProblema 29b
Capitolo 8, Problema 29b

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

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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.

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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.
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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.
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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.
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Percorso guidato
1:59
Alkene Metathesis Concept 5
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Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3

(c)

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

(a)

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

(d)

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

(a)

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

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