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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4:05 minutes

Problem 34k

Textbook Question

Predict the product(s) of the following reactions.
(k)

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Identify the functional groups present in the starting material. The molecule contains an ether linkage (R-O-R') and a cyclopentane ring.

Recognize the reagents used in the reaction. The presence of H2 and Pd/C indicates a catalytic hydrogenation reaction, which typically reduces double bonds or other unsaturated systems.

Consider the stability of the ether linkage under the reaction conditions. Ethers are generally stable to hydrogenation, so the ether bond is unlikely to be cleaved.

Evaluate the potential sites of hydrogenation. Since the molecule does not contain any double or triple bonds, the reaction may not proceed as typical hydrogenation.

Conclude that the reaction conditions may not significantly alter the structure of the starting material, as there are no unsaturated bonds to reduce.

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Key Concepts

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

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to a compound, typically in the presence of a catalyst such as palladium on carbon (Pd/C). This process is commonly used to reduce or saturate organic compounds, such as converting alkenes to alkanes. In the context of ethers, hydrogenation generally does not affect the ether linkage unless specific conditions are met.

Catalysis by Pd/C

Palladium on carbon (Pd/C) is a widely used catalyst in organic chemistry for hydrogenation reactions. It facilitates the addition of hydrogen to unsaturated bonds, such as double or triple bonds, under mild conditions. Pd/C is particularly effective due to its high surface area and ability to adsorb hydrogen, making it a versatile catalyst for various reduction reactions.

Stability of Ethers

Ethers are generally stable compounds that resist many types of chemical reactions, including hydrogenation. The ether linkage (C-O-C) is not typically affected by hydrogenation under standard conditions, as it lacks the unsaturated bonds that are usually targeted by such reactions. This stability is due to the strong C-O bond and the lack of reactive sites in the ether structure.

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Related Practice

Textbook Question

Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.

The reaction is thought to involve attack by a bromide ion on the Lewis acid–base adduct of the ether with BBr₃ (a strong Lewis acid). Propose a mechanism for the reaction of butyl methyl ether with BBr₃ to give (after hydrolysis) butan-1-ol and bromomethane.

Textbook Question

Predict the products of the following reactions. An excess of acid is available in each case.

(d)

Textbook Question

Predict the product of the following reactions.

(a)

Textbook Question

Predict the product of the following reactions.

(b)

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

When diethyl ether (CH₃CH₂OCH₂CH₃) is treated with concentrated HBr, the initial products are CH₃CH₂Br and CH₃CH₂OH. Propose a mechanism to account for this reaction.