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

10. Addition Reactions

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

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6:02 minutes

Problem 37

Textbook Question

How do the major products obtained from rearrangement of the following arene oxides differ?

Verified step by step guidance

Step 1: Analyze the given arene oxides. The structures provided are two arene oxides with isotopic labels (H and D) on the hydroxyl group and adjacent carbon. These isotopic labels will influence the rearrangement products due to their positions.

Step 2: Understand the rearrangement mechanism. Arene oxides typically undergo rearrangement via a NIH shift, where the substituent (hydrogen or deuterium) migrates to the adjacent carbon during the formation of phenols.

Step 3: Predict the migration pattern. In the first structure, the hydrogen (H) is positioned on the carbon adjacent to the oxygen, while deuterium (D) is on the hydroxyl group. During rearrangement, the hydrogen is likely to migrate to the oxygen-bearing carbon. In the second structure, the positions of H and D are reversed, so the deuterium will migrate instead.

Step 4: Consider the stereochemical implications. The migration of H or D will result in phenols with different isotopic labeling patterns. The major products will differ based on which isotope (H or D) migrates during the rearrangement.

Step 5: Conclude the difference in products. The major products obtained from the rearrangement of the two arene oxides will differ in the placement of isotopic labels (H and D) on the phenol ring, reflecting the migration patterns during the NIH shift.

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Key Concepts

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

Arene Oxides

Arene oxides are reactive intermediates formed from the oxidation of aromatic compounds. They typically contain an epoxide structure, where an oxygen atom is incorporated into the aromatic ring. Understanding their formation and reactivity is crucial, as they can undergo various rearrangements leading to different products, depending on the substituents on the aromatic ring and the reaction conditions.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule to form a different isomer. In the context of arene oxides, these reactions can lead to the formation of different products through mechanisms such as migration of substituents or ring opening. The specific pathways taken during rearrangement can significantly influence the nature and distribution of the final products.

Product Distribution

Product distribution refers to the relative amounts of different products formed in a chemical reaction. In the case of arene oxide rearrangements, factors such as sterics, electronics, and the stability of intermediates play a critical role in determining which products are favored. Analyzing product distribution helps chemists understand the underlying mechanisms and predict the outcomes of similar reactions.

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Related Practice

Textbook Question

Three arene oxides can be obtained from phenanthrene.

a. Draw the structures of the three phenanthrene oxides.

Textbook Question

Ethylene oxide reacts readily with HO^- because of the strain in the three-membered ring. Explain why cyclopropane, a compound with approximately the same amount of strain, does not react with HO^-.

Textbook Question

Propose a mechanism for each of the following reactions:

Textbook Question

Three arene oxides can be obtained from phenanthrene.

d. Which of the three phenanthrene oxides is most likely to be carcinogenic?

Textbook Question

What products are obtained from the reaction of cyclohexene oxide with

a. methoxide ion?

Textbook Question

Draw all possible resonance contributors for the two carbocations in the preceding reaction. Use the resonance contributors to explain why 1-naphthol is the major product of the reaction.

Textbook Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

b. What would be the major product if the carbocation forms phenol by losing H⁺ or D⁺, rather than by going through the NIH shift?

Textbook Question

Which of the following reactions occurs more rapidly?

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