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

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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Problem 22c

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?
(c)

Verified step by step guidance

Step 1: Understand the permanganate test. The permanganate test is used to identify the presence of unsaturation (double or triple bonds) or certain functional groups like alcohols or aldehydes. A positive test results in the purple KMnO₄ solution turning brown due to the formation of MnO₂.

Step 2: Analyze the given molecule. The structure provided is an ether, specifically diisopropyl ether. It contains no double or triple bonds and no functional groups like alcohols or aldehydes that can react with KMnO₄.

Step 3: Recall the reactivity of ethers. Ethers are generally inert to KMnO₄ under standard conditions because they lack the functional groups required for oxidation.

Step 4: Compare with the criteria for a positive permanganate test. Since the molecule does not have unsaturation or oxidizable functional groups, it would not give a positive permanganate test.

Step 5: Conclude that the molecule shown in the image would not result in the purple KMnO₄ solution turning brown, as it does not meet the requirements for a positive test.

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Key Concepts

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

Permanganate Test

The permanganate test is a qualitative analysis used to detect the presence of alkenes and alkynes in organic compounds. When these unsaturated hydrocarbons react with potassium permanganate (KMnO₄), the purple color of the solution is reduced to brown manganese dioxide (MnO₂), indicating a positive result. This reaction is due to the oxidation of the double or triple bonds present in the molecules.

Unsaturation in Organic Molecules

Unsaturation refers to the presence of double or triple bonds between carbon atoms in organic molecules. These unsaturated bonds are reactive and can participate in addition reactions, making them susceptible to oxidation by reagents like KMnO₄. Identifying whether a molecule is saturated (single bonds only) or unsaturated is crucial for predicting its behavior in the permanganate test.

Oxidation-Reduction Reactions

Oxidation-reduction (redox) reactions involve the transfer of electrons between substances, leading to changes in oxidation states. In the context of the permanganate test, the unsaturated organic compound is oxidized, while the permanganate ion is reduced, resulting in the color change from purple to brown. Understanding these reactions is essential for interpreting the results of the test and determining the presence of unsaturation in the tested molecules.

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Related Practice

Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.

(d)

Textbook Question

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(l)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(f)

Textbook Question

How might you make the catalytic cycle in Figure 9.31 more sustainable while still using NMO as the co-oxidant?

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Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(d)

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(f)

Textbook Question

Predict the major products of the following reactions, including stereochemistry.

e. trans-pent-2-ene + OsO₄/H₂O₂

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Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?(c)

Key Concepts

Permanganate Test

Unsaturation in Organic Molecules

Oxidation-Reduction Reactions

Watch next

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?
(c)