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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6:42 minutes

Problem 41c

Textbook Question

Three arene oxides can be obtained from phenanthrene.

c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?

Verified step by step guidance

Identify the structure of phenanthrene and locate the positions where epoxidation can occur to form arene oxides. Phenanthrene is a polycyclic aromatic hydrocarbon with three fused benzene rings.

Understand that arene oxides are formed by the epoxidation of the double bonds in the aromatic rings. In phenanthrene, the most reactive positions for epoxidation are typically at the 9,10 positions due to the higher electron density.

Consider the mechanism of arene oxide rearrangement to phenols. Arene oxides can undergo a rearrangement via a 1,2-hydride or 1,2-alkyl shift, leading to the formation of phenols.

Analyze the stability of the possible phenols formed from the rearrangement. The phenol that is more stable due to resonance or steric factors will generally be formed in greater yield.

Evaluate the regioselectivity of the rearrangement process. The phenol formed in greater yield will likely be the one where the rearrangement leads to a more stable carbocation intermediate, facilitating the shift and subsequent formation of the phenol.

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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, such as phenanthrene. They are characterized by an epoxide structure, where an oxygen atom is incorporated into the aromatic ring, creating a three-membered cyclic ether. Understanding the formation and reactivity of arene oxides is crucial for predicting the products of subsequent reactions, including the formation of phenols.

Phenol Formation

Phenols are organic compounds containing a hydroxyl (-OH) group attached to an aromatic ring. The formation of phenols from arene oxides typically involves nucleophilic attack by water or other nucleophiles, leading to ring-opening and rearrangement. The specific conditions and substituents on the aromatic ring can influence which phenol is produced and in what yield, making it essential to analyze the reaction pathways.

Reaction Mechanisms

Understanding reaction mechanisms is vital in organic chemistry as it explains the step-by-step process by which reactants transform into products. In the context of phenanthrene oxides, the mechanism will detail how the arene oxide can lead to different phenols, including factors that affect the yield of each phenol. Knowledge of mechanisms helps predict the most favorable pathways and the stability of intermediates, guiding the expected outcomes of the reaction.

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Related Practice

Textbook Question

What products are obtained from the reaction of cyclohexene oxide with

b. methylamine?

Textbook Question

b. A small amount of a product containing a six-membered ring is also formed. Draw the structure of that product.

c. Why is so little six-membered ring product formed?

Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?

a. trans-2-butene

b. cis-2-butene

Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?

c. cis-2-pentene

d. trans-2-pentene

Textbook Question

Cellosolve® is the trade name for 2-ethoxyethanol, a common industrial solvent. This compound is produced in chemical plants that use ethylene as their only organic feedstock. Show how you would accomplish this industrial process.

Textbook Question

Show the rest of the mechanism for formation of the cyclized intermediate in Figure 14-6.

Textbook Question

Predict the products of the following reactions.

(g) trans-2,3-epoxyoctane + H⁺, H₂O

(h) propylene oxide + methylamine (CH₃NH₂)

Textbook Question

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.

(a) Draw the enantiomers of propylene oxide.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide.

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Three arene oxides can be obtained from phenanthrene.c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?

Key Concepts

Arene Oxides

Phenol Formation

Reaction Mechanisms

Watch next

Three arene oxides can be obtained from phenanthrene.

c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?