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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

20. Phenols

Cleavage of Phenyl Ethers

Organic Chemistry

20. Phenols

Cleavage of Phenyl Ethers

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Multiple Choice

Choose the correct chemical sequence necessary for the following synthesis.

1. HBr (xs)/ heat

2. KOH

3. Benzyl bromide

1. HI (xs)/ heat

2. KOH

3. Bromobenzene

1. H₃O⁺

2. Br₂/ FeBr₃

3. NaOEt

1. HI (xs)/ heat

2. Benzyl bromide

3. KOH

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Verified step by step guidance

Analyze the starting material, which is phenethyl ether. The goal is to transform it into a compound with an additional benzene ring attached to the ethyl group.

Consider the first step: using an excess of a strong acid like HBr or HI with heat. This will cleave the ether bond, resulting in phenol and an ethyl halide (ethyl bromide or ethyl iodide).

In the second step, KOH is used. This is likely to deprotonate the phenol, forming phenoxide, which is a good nucleophile.

The third step involves the use of benzyl bromide. The phenoxide ion can perform a nucleophilic substitution on benzyl bromide, forming the desired ether linkage with the benzyl group.

Review the sequence of reactions: ether cleavage, formation of phenoxide, and nucleophilic substitution to form the final product. Ensure each step logically leads to the desired transformation.