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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4:44 minutes

Problem 39c,d

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.
(c) cyclooctanol + NaOCl/HOAC
(d) cyclopentylmethanol + CrO₃·pyridine·HCl

Verified step by step guidance

Step 1: Understand the reagents and their roles. For reaction (c), NaOCl (sodium hypochlorite) in the presence of HOAc (acetic acid) is a mild oxidizing agent. It oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. For reaction (d), CrO3・pyridine・HCl (Collins reagent) is a selective oxidizing agent that converts primary alcohols to aldehydes and secondary alcohols to ketones.

Step 2: Analyze the structure of cyclooctanol in reaction (c). Cyclooctanol is a secondary alcohol because the hydroxyl group (-OH) is attached to a carbon atom that is bonded to two other carbon atoms. When treated with NaOCl/HOAc, the secondary alcohol will be oxidized to a ketone. The product will retain the cyclooctane ring structure, with the ketone group replacing the hydroxyl group.

Step 3: Consider stereochemistry for reaction (c). Since the starting material is cyclooctanol, which is a cyclic compound, the stereochemistry of the product will depend on the stereochemistry of the starting alcohol. However, oxidation of a secondary alcohol to a ketone typically results in the loss of stereochemistry at the carbon bearing the hydroxyl group, as the ketone is planar (sp2 hybridized).

Step 4: Analyze the structure of cyclopentylmethanol in reaction (d). Cyclopentylmethanol is a primary alcohol because the hydroxyl group is attached to a carbon atom that is bonded to only one other carbon atom. When treated with CrO3・pyridine・HCl, the primary alcohol will be oxidized to an aldehyde. The product will retain the cyclopentane ring structure, with the aldehyde group replacing the hydroxymethyl group.

Step 5: Summarize the major products. For reaction (c), the major product is cyclooctanone, a ketone. For reaction (d), the major product is cyclopentylmethanal, an aldehyde. Ensure to consider the planar nature of the ketone and aldehyde functional groups when discussing stereochemistry.

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Key Concepts

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

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, this often pertains to the conversion of alcohols to carbonyl compounds (aldehydes or ketones) or carboxylic acids. Understanding the specific reagents used, such as CrO3 in the presence of pyridine, is crucial for predicting the products of these reactions.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving chiral centers, the stereochemical outcome can be significant, leading to different products based on the configuration of the starting materials. Recognizing stereochemical implications is essential when predicting the major products of reactions.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions can greatly influence the outcome of organic reactions. For example, NaOCl in acetic acid (HOAc) is a mild oxidizing agent that can selectively oxidize alcohols, while CrO3 in pyridine is a stronger oxidant that can fully oxidize primary alcohols to carboxylic acids. Understanding how these reagents interact with substrates is key to predicting the products.

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Related Practice

Textbook Question

Predict the major products of the following reactions.

(c)

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

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC

c. 4-hydroxydecanal

Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

c. 4-hydroxydecanal

Textbook Question

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