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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4:52 minutes

Problem 15d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the structure of the reactant. The reactant is a cyclic ether (specifically, a benzopyran structure) with an oxygen atom in a six-membered ring fused to a benzene ring.

Step 2: Recognize the role of HI (hydroiodic acid) in the reaction. HI is a strong acid and a source of iodide ions (I⁻). It can protonate the oxygen atom in the ether, making it susceptible to cleavage.

Step 3: Protonation of the oxygen atom occurs first. The lone pair of electrons on the oxygen atom interacts with the hydrogen ion (H⁺) from HI, forming a positively charged oxonium ion.

Step 4: The bond between the oxygen atom and one of the adjacent carbon atoms breaks, leading to the formation of two products. The iodide ion (I⁻) attacks the positively charged carbon atom, resulting in the formation of an alkyl iodide.

Step 5: The other product formed is a phenol group (benzene ring with an -OH group attached) due to the cleavage of the ether bond. The final products are phenol and an alkyl iodide.

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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.

Reaction Mechanisms

A reaction mechanism outlines the step-by-step process by which reactants convert into products. It includes the formation and breaking of bonds, intermediates, and transition states. Familiarity with common mechanisms, such as nucleophilic substitution or electrophilic addition, is essential for predicting the outcome of reactions, especially when excess reagents are involved.

Functional Group Transformations

Functional groups are specific groups of atoms within molecules that determine their chemical reactivity. In organic reactions, the presence of certain functional groups can dictate the type of reaction that occurs. Recognizing how excess acid can affect functional groups, such as converting alcohols to alkyl halides or facilitating esterification, is vital for predicting reaction products.

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