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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1:17 minutes

Problem 34c

Textbook Question

Predict the major products of the following reactions.
(c)

Verified step by step guidance

Step 1: Identify the functional groups in the given molecule. The molecule contains an aldehyde group (-CHO) and a ketone group (C=O) attached to a cyclohexane ring.

Step 2: Recognize the reagent used in the reaction. The reagent is Tollens' reagent, which consists of [Ag(NH3)2]+ and OH-. Tollens' reagent selectively oxidizes aldehydes to carboxylic acids while leaving ketones unaffected.

Step 3: Predict the reaction mechanism. The aldehyde group (-CHO) will be oxidized by Tollens' reagent to form a carboxylic acid group (-COOH). The ketone group (C=O) will remain unchanged because Tollens' reagent does not react with ketones.

Step 4: Write the structure of the major product. Replace the aldehyde group (-CHO) with a carboxylic acid group (-COOH) while keeping the ketone group (C=O) intact.

Step 5: Verify the stereochemistry and connectivity of the product. Ensure that the cyclohexane ring remains unchanged and the functional groups are correctly positioned in the major product.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity patterns and the types of reactions that can occur, which is essential for determining the major products of a reaction.

Regioselectivity and Stereoselectivity

Regioselectivity refers to the preference of a chemical reaction to occur at one location over another in a molecule, while stereoselectivity involves the preference for the formation of one stereoisomer over others. Understanding these concepts is vital for predicting the major products, especially in reactions involving multiple possible sites of reaction or stereochemical outcomes.

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Related Practice

Textbook Question

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(a)

Textbook Question

The intermediates for the Swern oxidation, a reaction introduced in Section 13.9.4, are shown. Provide the arrow-pushing mechanism that rationalizes the formation of each intermediate and the final product(s).

Textbook Question

What product is obtained from the reaction of each of the following alcohols with

a. H₂CrO₄?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol

Textbook Question

What product is obtained from the reaction of each of the following alcohols with

c. the regents required for a Swern oxidation?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol

Textbook Question

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

(d) CH₃CH₂CH₂CH₂CH(OH)OCH₃

(e) CH₃CH₂CH₂CH₂CH(OCH₃)₂

(f)

Textbook Question

The following reaction involves a starting material with a double bond and a hydroxy group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.

Textbook Question

Predict the products formed by periodic acid cleavage of the following diols.

(c)

(d)

Textbook Question

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

(d) cyclopentylmethanol + CrO₃·pyridine·HCl

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