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

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2:05 minutes

Problem 47e

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(e) hot, concentrated potassium permanganate

Verified step by step guidance

Step 1: Analyze the structure of limonene. Limonene is a cyclic terpene with two double bonds: one in the six-membered ring and one in the exocyclic position. These double bonds are susceptible to oxidation reactions.

Step 2: Understand the reagent used. Hot, concentrated potassium permanganate (KMnO₄) is a strong oxidizing agent that can cleave double bonds and oxidize them to carboxylic acids or ketones, depending on the structure of the molecule.

Step 3: Predict the reaction at the exocyclic double bond. The exocyclic double bond will undergo oxidative cleavage, resulting in the formation of a carboxylic acid group at the terminal carbon and another carboxylic acid group at the adjacent carbon.

Step 4: Predict the reaction at the double bond within the ring. The double bond in the ring will also undergo oxidative cleavage, breaking the ring and forming two carboxylic acid groups at the carbons originally involved in the double bond.

Step 5: Combine the products. The final products will include multiple carboxylic acid groups resulting from the cleavage of both double bonds. The cyclic structure of limonene will be broken, and the molecule will be fully oxidized to carboxylic acids.

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Key Concepts

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

Limonene Structure and Properties

Limonene is a cyclic monoterpene with a distinctive structure characterized by a six-membered ring and a double bond. It is known for its citrus aroma and is commonly found in the peels of citrus fruits. Understanding its structure is crucial for predicting its reactivity with various reagents.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, often resulting in the formation of alcohols, ketones, or carboxylic acids. In the case of limonene reacting with hot, concentrated potassium permanganate, it undergoes oxidative cleavage, leading to the formation of carboxylic acids or other oxidized products.

Potassium Permanganate as an Oxidizing Agent

Potassium permanganate (KMnO4) is a strong oxidizing agent used in organic chemistry to oxidize alkenes and other functional groups. When used in concentrated and heated conditions, it can cleave double bonds and oxidize hydrocarbons to form various products, making it essential for understanding the expected outcomes of reactions involving limonene.

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Related Practice

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

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.

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Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.(e) hot, concentrated potassium permanganate

Key Concepts

Limonene Structure and Properties

Oxidation Reactions

Potassium Permanganate as an Oxidizing Agent

Watch next

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(e) hot, concentrated potassium permanganate