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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Problem 106f(ix,x)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'
(f)

Verified step by step guidance

Identify the structure of the given molecule. The image shows a tertiary alcohol, specifically 2-methyl-2-phenylpropan-2-ol.

Understand the reagents: PCC (Pyridinium chlorochromate) is a mild oxidizing agent that typically oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. H₂CrO₄ (chromic acid) is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones.

Recognize that tertiary alcohols, like the one in the image, generally do not undergo oxidation with either PCC or H₂CrO₄ because there is no hydrogen atom on the carbon bearing the hydroxyl group to be removed during the oxidation process.

Predict the outcome for reaction (ix) with PCC: Since the molecule is a tertiary alcohol, no reaction will occur because PCC cannot oxidize tertiary alcohols.

Predict the outcome for reaction (x) with H₂CrO₄, H₂O: Similarly, no reaction will occur with H₂CrO₄ as it also cannot oxidize tertiary alcohols.

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Key Concepts

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

PCC (Pyridinium Chlorochromate)

PCC is a mild oxidizing agent commonly used in organic chemistry to convert primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation. It is favored for its ability to selectively oxidize alcohols while minimizing side reactions, making it useful in synthetic pathways where specific functional groups need to be preserved.

H₂CrO₄ (Chromic Acid)

H₂CrO₄ is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Its reactivity is higher than that of PCC, which means it can lead to over-oxidation if not controlled. Understanding its reactivity is crucial for predicting the outcomes of reactions involving alcohols and other functional groups.

Oxidation States and Functional Group Transformations

In organic chemistry, oxidation refers to the increase in oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. Recognizing how different reagents affect the oxidation states of functional groups is essential for predicting reaction products. This concept helps in understanding how alcohols can be transformed into aldehydes, ketones, or carboxylic acids depending on the oxidizing agent used.

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Related Practice

Textbook Question

Draw a mechanism for the following oxidation reactions.

(c)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(o)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(f)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(k)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(c)

Textbook Question

(a) Based on Figure 24.23, explain why meta-dihydroxybenzene is not oxidized to meta-quinone.

(b) If a meta-quinone is not produced, what would you expect the product of the oxidation of meta-dihydroxybenzene to be?

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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'(f)

Key Concepts

PCC (Pyridinium Chlorochromate)

H₂CrO₄ (Chromic Acid)

Oxidation States and Functional Group Transformations

Watch next

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'
(f)