Predict the major, organic product for the following reaction. <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch13_Q11_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 1 is single bonded to O on the upper right. O is single bonded to C H 3 on the right in the form of a line. C 1 is single bonded to C H 3 on the upper left in the form of a line. The second reactant is H C l written over the reaction arrow. One equivalent of the second reactant is used." />

Table of contents

Skip topic navigation

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

Previous problemNext problem

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structures of two products. The first product has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 1 is single bonded to C l on the upper right. C 1 is single bonded to C H 3 on the upper left in the form of a line. The second product is H O in which O is single bonded to C H 3 on the right in the form a line.

Previous problemNext problem

Verified step by step guidance

Identify the starting material: The starting material is a tertiary alkoxide ion, specifically a tert-butoxide ion attached to a cyclopentane ring.

Recognize the reagent: The reagent used is hydrochloric acid (HCl), which is a strong acid capable of protonating the alkoxide ion.

Consider the mechanism: The reaction likely proceeds via an acid-base mechanism where the alkoxide ion is protonated by HCl, forming an alcohol and releasing a chloride ion.

Predict the major product: Protonation of the alkoxide ion will convert it into the corresponding alcohol, tert-butyl alcohol, while the chloride ion remains as a byproduct.

Evaluate the stability: The tertiary alcohol formed is stable, and the reaction is driven by the formation of a stable alcohol and the release of a chloride ion.