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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4:50 minutes

Problem 15c

Textbook Question

Predict the products of the following reactions. An excess of acid is available in each case.
(c) anisole (methoxybenzene) + HBr

Verified step by step guidance

Identify the type of reaction taking place. In this case, since an excess of acid is available, consider the possibility of an acid-catalyzed reaction such as hydration, esterification, or hydrolysis.

Examine the structure of the reactants. Look for functional groups that are reactive in the presence of acid, such as alkenes, alcohols, or esters.

Determine the mechanism of the reaction. For example, if the reactant is an alkene, the reaction might proceed through an electrophilic addition mechanism where the acid protonates the alkene to form a carbocation intermediate.

Predict the formation of intermediates. In the case of a carbocation intermediate, consider possible rearrangements that could lead to a more stable carbocation.

Identify the final products by considering the stability of the intermediates and the possible nucleophiles present in the reaction mixture. For example, water could act as a nucleophile in an acid-catalyzed hydration reaction, leading to the formation of an alcohol.

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Key Concepts

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

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, acids can donate protons, while bases accept them. Understanding the role of acids in promoting reactions, especially in the presence of excess acid, is crucial for predicting the products formed in various organic transformations.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism where a nucleophile attacks an electrophile, replacing a leaving group. This concept is essential for predicting products in reactions involving alkyl halides or other electrophilic centers, especially when acid catalysis can enhance the nucleophilicity of the attacking species.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule, often facilitated by acidic conditions. These reactions can lead to the formation of more stable products or different isomers. Recognizing when and how rearrangements occur is vital for accurately predicting the outcomes of organic reactions under acidic conditions.

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Suggest the reagents used to effect the transformations shown.

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Suggest a mechanism by which TXB₂ might be formed from TXA₂ in an acid-catalyzed hydrolysis reaction. [The structure has been simplified.]

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Propose a mechanism for each of the following reactions:

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What is the major product(s) of each of the following reactions?

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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)

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