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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5:29 minutes

Problem 4c(1,2)

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

Verified step by step guidance

Step 1: Understand the reagents and their roles. Sodium dichromate (Na₂Cr₂O₇) in the presence of sulfuric acid (H₂SO₄) is a strong oxidizing agent. It can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Pyridinium chlorochromate (PCC) is a milder oxidizing agent that oxidizes primary alcohols to aldehydes and secondary alcohols to ketones without further oxidation to carboxylic acids.

Step 2: Analyze the structure of 4-hydroxydecanal. It contains both an aldehyde (-CHO) group and a hydroxyl (-OH) group. The hydroxyl group is on the fourth carbon, and the aldehyde group is on the first carbon of the decanal chain.

Step 3: Predict the reaction with Na₂Cr₂O₇/H₂SO₄. The strong oxidizing agent will oxidize the primary alcohol (if present) to a carboxylic acid. However, in this case, the aldehyde group (-CHO) will be further oxidized to a carboxylic acid (-COOH). The hydroxyl group on the fourth carbon will remain unaffected as it is a secondary alcohol.

Step 4: Predict the reaction with PCC. PCC, being a milder oxidizing agent, will not oxidize the aldehyde group further. It will leave the aldehyde group intact and will not affect the secondary alcohol group on the fourth carbon.

Step 5: Summarize the products. For Na₂Cr₂O₇/H₂SO₄, the product will be 4-hydroxydecanoic acid (the aldehyde oxidized to a carboxylic acid). For PCC, the product will remain 4-hydroxydecanal as PCC does not oxidize aldehydes or secondary alcohols further.

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Key Concepts

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

Oxidation of Alcohols

Alcohols can undergo oxidation to form carbonyl compounds, such as aldehydes or ketones, depending on the structure of the alcohol and the oxidizing agent used. Primary alcohols typically oxidize to aldehydes, while secondary alcohols oxidize to ketones. Tertiary alcohols do not oxidize easily due to the lack of a hydrogen atom on the carbon bearing the hydroxyl group.

Oxidizing Agents

Different oxidizing agents can yield different products from alcohols. Sodium dichromate (Na2Cr2O7) in acidic conditions is a strong oxidizer that can fully oxidize primary alcohols to carboxylic acids, while pyridinium chlorochromate (PCC) is milder and typically oxidizes primary alcohols to aldehydes without further oxidation to carboxylic acids.

Functional Group Transformation

The transformation of functional groups is a key concept in organic chemistry. In the case of 4-hydroxydecanal, the hydroxyl (-OH) group can be oxidized to a carbonyl group (C=O), resulting in the formation of a ketone or aldehyde, depending on the oxidation conditions. Understanding how functional groups react and change is essential for predicting the products of organic reactions.

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Related Practice

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

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.