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(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.'
(f)

Verified step by step guidance

Identify the structure of the given molecule: The molecule is a tertiary alcohol, specifically 2-phenyl-2-propanol.

Consider the reaction with HOCl, H₂O: Tertiary alcohols can undergo halogenation with HOCl to form alkyl chlorides. The hydroxyl group will be replaced by a chlorine atom.

Write the reaction mechanism for HOCl: The hydroxyl group is protonated by H⁺ from HOCl, forming water as a leaving group. The carbocation intermediate is then attacked by Cl⁻, resulting in the formation of 2-chloro-2-phenylpropane.

Consider the reaction with HIO₄: Periodic acid (HIO₄) is typically used to cleave vicinal diols (1,2-diols) into aldehydes or ketones. Since the given molecule is not a diol, no reaction will occur with HIO₄.

Summarize the products: The reaction with HOCl will yield 2-chloro-2-phenylpropane, while no reaction will occur with HIO₄.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the context of phenols, the hydroxyl group (OH) activates the benzene ring, making it more susceptible to electrophilic attack, particularly at the ortho and para positions. This concept is crucial for predicting reactions involving aromatic compounds with substituents.

Oxidation of Alcohols

Alcohols can undergo oxidation to form carbonyl compounds. The presence of oxidizing agents like HOCl can convert secondary alcohols into ketones. In the given structure, the tertiary alcohol group is resistant to oxidation under typical conditions, which is important for predicting the reaction outcome with oxidizing agents.

Periodic Acid (HIO₄) Cleavage

Periodic acid (HIO₄) is known for cleaving vicinal diols, breaking the C-C bond between them to form carbonyl compounds. However, in the absence of vicinal diols, as in the given structure, no reaction occurs. Understanding this selective cleavage is essential for predicting the reactivity of compounds with periodic acid.

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Related Practice

Textbook Question

Draw a mechanism for the following oxidation reactions.

(d)

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: (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

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)

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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.'(f)

Key Concepts

Electrophilic Aromatic Substitution

Oxidation of Alcohols

Periodic Acid (HIO₄) Cleavage

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.'
(f)