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 106c(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.'
(c)

Verified step by step guidance

Identify the functional groups present in the molecule. In this case, the molecule contains two alcohol groups (OH).

Consider the reaction conditions (xi) HOCl, H₂O. This is a hypochlorous acid in water, which can act as an oxidizing agent. It can convert alcohols to chlorohydrins.

For the reaction with HOCl, H₂O, the secondary alcohol group is more likely to react, forming a chlorohydrin by replacing the OH group with a Cl atom.

Consider the reaction conditions (xii) HIO₄. Periodic acid (HIO₄) is known to cleave vicinal diols (1,2-diols) into aldehydes or ketones.

For the reaction with HIO₄, the vicinal diol (the two adjacent OH groups) will be cleaved, resulting in the formation of two carbonyl compounds, typically ketones or aldehydes, depending on the structure of the original diol.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically occurring in alkenes and alkynes. In the context of HOCl and HIO₄, understanding how these reagents interact with double or triple bonds is crucial for predicting the products. The electrophile attacks the nucleophilic site, leading to the formation of new bonds and potentially rearranging the structure of the original molecule.

Oxidation-Reduction Reactions

Oxidation-reduction (redox) reactions involve the transfer of electrons between species, resulting in changes in oxidation states. HIO₄ is a strong oxidizing agent that can cleave carbon-carbon bonds and oxidize alcohols to carbonyl compounds. Recognizing whether a reaction leads to oxidation or reduction is essential for predicting the final products of the reactions in question.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another. In the reactions with HOCl and HIO₄, it is important to identify the functional groups present in the starting materials and how they may change during the reaction. This understanding helps in predicting the structure of the products formed after the reaction, including any potential rearrangements or eliminations.

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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.'

(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.'

(k)

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?

Textbook Question

In Hinkley, the cleanup continues today. In one process PG&E is using to mitigate the chromium(VI) toxicity, ethanol is injected into the soil. How would this reduce the chromium(VI) contamination?

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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.'(c)

Key Concepts

Electrophilic Addition Reactions

Oxidation-Reduction Reactions

Functional Group Transformations

Watch next

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)