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

12. Alcohols, Ethers, Epoxides and Thiols

Ether Cleavage

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Ether Cleavage

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Problem 35c

Textbook Question

Suggest the reagents used to effect the transformations shown.
(c)

Verified step by step guidance

Identify the starting material and the products. The starting material is an ether with a phenyl group and a cyclopropyl group. The products are toluene and cyclopropanol.

Recognize that the transformation involves breaking the ether bond and forming an alcohol group on the cyclopropyl moiety while converting the phenyl group to toluene.

Consider the mechanism of ether cleavage. Acidic conditions are typically used to cleave ethers, often involving a strong acid like HBr or HI.

Propose the use of a strong acid such as HBr or HI to cleave the ether bond. The acid will protonate the ether oxygen, making it a better leaving group.

The protonated ether can then undergo nucleophilic attack by the halide ion, leading to the formation of toluene and cyclopropanol as the final products.

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Key Concepts

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

Ether Cleavage

Ether cleavage involves breaking the C-O bond in ethers, typically using strong acids like HI or HBr. The reaction often results in the formation of alcohols and alkyl halides. In this transformation, the ether is cleaved to produce a phenol and a cyclic ether, indicating the use of acidic conditions to facilitate the cleavage.

Acidic Conditions

Acidic conditions are crucial for ether cleavage, as they protonate the ether oxygen, making the C-O bond more susceptible to nucleophilic attack. Common acids used include hydrobromic acid (HBr) or hydroiodic acid (HI), which can effectively cleave ethers to form alcohols and other products, as seen in the transformation to phenol and a cyclic ether.

Phenol Formation

Phenol formation in ether cleavage reactions occurs when the aromatic ring stabilizes the resulting carbocation, allowing the formation of a stable phenol product. This stability is due to resonance within the aromatic ring, which is a key factor in the transformation shown, where the ether is cleaved to yield a phenol and a cyclic ether.