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 106k(xi,xii)

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)

Verified step by step guidance

Identify the functional groups present in the given molecule. The structure shows a cyclohexane ring with a tertiary alcohol group attached.

Consider the reaction conditions (xi) HOCl, H₂O. This is a hypochlorous acid in water, which typically adds across double bonds or reacts with alcohols to form chlorohydrins.

Since the molecule contains a tertiary alcohol, HOCl can react with the alcohol to form a chlorohydrin. The hydroxyl group will be replaced by a chlorine atom.

Next, consider the reaction conditions (xii) HIO₄. Periodic acid (HIO₄) is known for cleaving vicinal diols (1,2-diols) into aldehydes or ketones. However, since the molecule does not have a vicinal diol, no reaction will occur under these conditions.

Summarize the expected outcomes: Under condition (xi), the tertiary alcohol will be converted to a tertiary chloride. Under condition (xii), no reaction will occur as there is no vicinal diol present.

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Key Concepts

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

Oxidation of Alcohols

Oxidation of alcohols involves the conversion of an alcohol group into a carbonyl group. Primary alcohols can be oxidized to aldehydes or further to carboxylic acids, while secondary alcohols are typically oxidized to ketones. Tertiary alcohols generally do not undergo oxidation under mild conditions due to the lack of a hydrogen atom on the carbon bearing the hydroxyl group.

Periodic Acid (HIO₄) Cleavage

Periodic acid (HIO₄) is used to cleave vicinal diols, breaking the C-C bond between the two hydroxyl-bearing carbons and forming two carbonyl compounds. This reaction is specific to 1,2-diols and does not occur if the hydroxyl groups are not adjacent. In the absence of vicinal diols, no reaction occurs with HIO₄.

Reactivity of HOCl with Alcohols

Hypochlorous acid (HOCl) can react with alcohols to form alkyl hypochlorites, which can further undergo rearrangement or elimination reactions. The reaction is more favorable with primary and secondary alcohols, where the formation of a carbocation intermediate is possible. Tertiary alcohols may not react significantly due to steric hindrance and the stability of the starting material.

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Related Practice

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.'

(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.'

(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?

Textbook Question

Predict the product of the oxidation reactions shown.

(b)

Textbook Question

If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?

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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)

Key Concepts

Oxidation of Alcohols

Periodic Acid (HIO₄) Cleavage

Reactivity of HOCl with Alcohols

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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)