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

Ozonolysis

Organic Chemistry

10. Addition Reactions

Ozonolysis

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8:50 minutes

Problem 31b

Textbook Question

What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage

Verified step by step guidance

Identify the reaction type: Oxidative cleavage of alkenes typically involves reagents like ozone (O₃) followed by a reducing agent (e.g., Zn/H₂O) or KMnO₄ under acidic conditions. This reaction breaks the double bond and converts the resulting fragments into carbonyl compounds (aldehydes or ketones).

Determine the product: The problem specifies that the product is an aldehyde with four carbons. This means the alkene must be cleaved in such a way that one of the fragments forms an aldehyde with exactly four carbon atoms.

Analyze the structure of the product: An aldehyde with four carbons has the general formula CH₃(CH₂)₂CHO. This indicates that the alkene must have been cleaved to produce this specific aldehyde fragment.

Work backward to deduce the alkene: To form an aldehyde with four carbons, the double bond in the alkene must be positioned such that one of the resulting fragments after cleavage is CH₃(CH₂)₂CHO. For example, the alkene could be 1-hexene (CH₂=CH(CH₂)₃CH₃) or 2-hexene (CH₃CH=CH(CH₂)₂CH₃), as these would yield the desired aldehyde upon oxidative cleavage.

Verify the possibilities: Ensure that the proposed alkenes meet the criteria of producing only the specified aldehyde as a product. For example, symmetrical alkenes like 2-hexene would produce two identical aldehyde molecules, while unsymmetrical alkenes like 1-hexene would produce one aldehyde and one other fragment.

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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 smaller carbonyl compounds, typically aldehydes or ketones, through the addition of oxidizing agents. This process involves the cleavage of the carbon-carbon double bond, resulting in the formation of carbonyl groups. Understanding the conditions and reagents used in oxidative cleavage is crucial for predicting the products formed from specific alkenes.

Aldehyde Structure

Aldehydes are organic compounds characterized by the presence of a carbonyl group (C=O) at the end of a carbon chain. The general formula for aldehydes is RCHO, where R represents a hydrocarbon group. In the context of the question, identifying alkenes that yield a four-carbon aldehyde requires knowledge of how the carbon skeleton is rearranged during oxidative cleavage.

Alkene Reactivity

Alkenes are unsaturated hydrocarbons with at least one carbon-carbon double bond, making them reactive towards various chemical reactions, including oxidation. The position and substitution of the double bond in the alkene influence the products formed during reactions. Recognizing which alkenes can lead to a specific aldehyde product is essential for solving the question regarding oxidative cleavage.

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Related Practice

Textbook Question

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

(b)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O (viii) 1. O₃ 2. CH₃SCH₃

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O₃ 2. CH₃SCH₃

(f)

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

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

Textbook Question

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

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