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

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

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1:49 minutes

Problem 53g

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.
g. Tollens reagent

Verified step by step guidance

Step 1: Recognize the functional group in cyclohexanone. Cyclohexanone is a ketone, characterized by a carbonyl group (C=O) bonded to two alkyl groups.

Step 2: Understand the nature of Tollens reagent. Tollens reagent is an aqueous solution of silver nitrate (AgNO₃) and ammonia (NH₃), which is used to test for aldehydes. It oxidizes aldehydes to carboxylic acids and reduces Ag⁺ ions to metallic silver (Ag).

Step 3: Determine the reactivity of ketones with Tollens reagent. Ketones, unlike aldehydes, generally do not react with Tollens reagent because they cannot be oxidized under these conditions. The carbonyl group in ketones is less reactive toward oxidation due to the absence of a hydrogen atom directly bonded to the carbonyl carbon.

Step 4: Predict the outcome of the reaction. Since cyclohexanone is a ketone, it will not react with Tollens reagent, and no oxidation or reduction will occur. The solution will remain unchanged, and no silver mirror will form.

Step 5: Summarize the result. Cyclohexanone does not produce any products when treated with Tollens reagent because ketones are resistant to oxidation by this reagent.

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Key Concepts

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

Tollens' Reagent

Tollens' reagent is a solution of silver nitrate in ammonia, commonly used to test for aldehydes. It contains the complex ion [Ag(NH3)2]+, which oxidizes aldehydes to carboxylic acids while reducing silver ions to metallic silver. In the case of cyclohexanone, which is a ketone, it does not react with Tollens' reagent, as ketones are generally not oxidized by this reagent.

Oxidation-Reduction Reactions

Oxidation-reduction (redox) reactions involve the transfer of electrons between substances, leading to changes in oxidation states. In organic chemistry, oxidation often refers to the addition of oxygen or the removal of hydrogen, while reduction is the opposite. Understanding these concepts is crucial for predicting the outcomes of reactions involving reagents like Tollens' reagent, which specifically oxidizes aldehydes but not ketones.

Reactivity of Ketones vs. Aldehydes

Ketones and aldehydes are both carbonyl compounds, but they differ in reactivity due to their structural features. Aldehydes have at least one hydrogen atom attached to the carbonyl carbon, making them more susceptible to oxidation. In contrast, ketones, such as cyclohexanone, have two alkyl groups attached to the carbonyl carbon, which makes them less reactive towards oxidizing agents like Tollens' reagent.

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Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(a) CH₃CH₂CH₂COCH₃

(b) CH₃CH₂CH₂CH₂CHO

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A chemist attempted to oxidize a primary alcohol to a carboxylic acid using chromic acid. The product shown was obtained as a major component in the mixture. Suggest an arrow-pushing mechanism that accounts for its formation. [Think about what chromic acid would normally do to a phenol and make a list of bonds formed and bonds broken.]

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Predict the product of the following oxidation reactions.

(d)

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