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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6:56 minutes

Problem 24c,d

Textbook Question

What are the major products obtained when each of the following ethers is heated with one equivalent of HI?
c.
d.

Verified step by step guidance

Step 1: Understand the reaction mechanism. When ethers are treated with hydrogen iodide (HI), they undergo cleavage via an SN2 or SN1 mechanism depending on the structure of the ether. The reaction typically produces an alcohol and an alkyl iodide.

Step 2: Analyze the structure of the given ethers. For each ether, identify the alkyl groups attached to the oxygen atom. Determine whether the alkyl groups are primary, secondary, or tertiary, as this will influence the reaction pathway (SN2 or SN1).

Step 3: Predict the site of cleavage. In the case of an SN2 mechanism, the less sterically hindered alkyl group will be attacked by the iodide ion (I⁻), leading to the formation of an alkyl iodide and an alcohol. For an SN1 mechanism, the more stable carbocation will form, leading to the corresponding products.

Step 4: Write the reaction products. For each ether, show the cleavage of the C-O bond and the formation of the alcohol and alkyl iodide. Use the structural information from Step 2 to determine the major products.

Step 5: Verify the major products. Consider factors such as steric hindrance, carbocation stability, and the reactivity of the alkyl groups to confirm the major products for each ether when treated with one equivalent of HI.

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Key Concepts

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

Ethers

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. They are generally stable and non-reactive under normal conditions but can undergo cleavage reactions when treated with strong acids, such as hydroiodic acid (HI). Understanding the structure and reactivity of ethers is crucial for predicting the products formed during their reaction with HI.

Acid-Catalyzed Cleavage

Acid-catalyzed cleavage of ethers involves the protonation of the ether oxygen, making the ether bond more susceptible to nucleophilic attack. When heated with HI, the ether is cleaved to form an alcohol and an alkyl iodide. This reaction is significant in organic synthesis as it allows for the generation of useful products from relatively stable starting materials.

Reaction Mechanism

The reaction mechanism for ether cleavage by HI typically involves two main steps: protonation of the ether oxygen followed by nucleophilic attack by iodide ion. This mechanism highlights the importance of understanding the role of acids and nucleophiles in organic reactions, as well as the stability of intermediates formed during the process. A clear grasp of these mechanisms is essential for predicting the major products of the reaction.

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