Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Oxidative Cleavage

Organic Chemistry

10. Addition Reactions

Oxidative Cleavage

Previous problemNext problem

5:14 minutes

Problem 31a

Textbook Question

What alkene would give only a ketone with three carbons as a product of oxidative cleavage?

Verified step by step guidance

Identify the reaction type: Oxidative cleavage of alkenes typically involves breaking the double bond and forming carbonyl compounds (ketones or aldehydes) depending on the substituents attached to the double bond. In this case, the product is specified as a ketone with three carbons.

Recall the structure of a ketone: A ketone has the general formula R-CO-R', where the carbonyl group (C=O) is bonded to two alkyl groups. For a three-carbon ketone, the structure would be CH3-CO-CH3 (acetone).

Work backward to determine the alkene: To form a ketone upon oxidative cleavage, the double bond in the alkene must be flanked by two alkyl groups. For acetone, the alkene must have a structure where the double bond is between two methyl groups, such as 2,3-dimethyl-2-butene.

Verify the oxidative cleavage process: When the double bond in 2,3-dimethyl-2-butene undergoes oxidative cleavage (e.g., using reagents like ozone followed by reductive workup or KMnO4 under acidic conditions), the bond breaks, and each carbon of the double bond forms a carbonyl group. This results in two molecules of acetone.

Conclude the reasoning: The alkene that would give only a ketone with three carbons (acetone) as the product of oxidative cleavage is 2,3-dimethyl-2-butene.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Oxidative Cleavage

Oxidative cleavage is a reaction where alkenes are broken down into carbonyl compounds, such as aldehydes and ketones, typically using reagents like ozone (O3) or potassium permanganate (KMnO4). This process involves the addition of oxygen across the double bond, leading to the formation of carbonyl groups. Understanding this reaction is crucial for predicting the products formed from specific alkenes.

Alkene Structure

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. The position and substitution of this double bond significantly influence the reactivity of the alkene during oxidative cleavage. Identifying the correct alkene structure is essential to determine which alkene will yield a specific carbonyl product, such as a ketone with three carbons.

Ketone Formation

Ketones are organic compounds characterized by a carbonyl group (C=O) flanked by two carbon atoms. In the context of oxidative cleavage, a ketone is formed when the cleavage of an alkene results in a carbonyl group being attached to two alkyl groups. Recognizing the conditions under which a ketone is produced, particularly from a three-carbon chain, is vital for solving the given question.

Watch next

Master General properties of strong oxidative cleavage. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Predict the major products of the following reactions.

(e) 1-ethylcycloheptene + warm, concentrated KMnO₄

Textbook Question

Unknown X, C₅H₉Br does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C₅H₈. Unlike X, Y decolorizes bromine and changes KMnO₄ from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C₅H₈O₂. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

Textbook Question

An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic reduction to give decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-cyclohexane-1,2-dicarboxylic acid and oxalic acid. Propose a structure for the unknown compound.

Multiple Choice

Predict the product of the following reaction.

Textbook Question

Predict the major products of the following reactions.

(b) (Z)-3-methyloct-3-ene + warm, concentrated KMnO₄

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(k)

Textbook Question

The sex attractant of the housefly has the formula C₂₃H₄₆. When treated with warm potassium permanganate, this pheromone gives two products: CH₃(CH₂)₁₂COOH and CH₃(CH₂)₇COOH. Suggest a structure for this sex attractant. Explain which part of the structure is uncertain.

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(b) hex-3-ene → propanoic acid

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap