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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3:52 minutes

Problem 24e

Textbook Question

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

Verified step by step guidance

Identify the structure of the ether in question. Ethers have the general formula R-O-R', where R and R' are alkyl or aryl groups. Determine the specific groups attached to the oxygen atom in the given ether.

Understand the reaction mechanism: When an ether reacts with HI, the bond between the oxygen and one of the alkyl groups (R or R') is cleaved. This occurs via an SN2 or SN1 mechanism, depending on the nature of the alkyl groups. Primary and secondary alkyl groups typically undergo SN2, while tertiary alkyl groups favor SN1.

Determine which bond will break: The bond between the oxygen and the less sterically hindered alkyl group (or the group that forms a more stable carbocation in the case of SN1) is more likely to break. This results in the formation of an alcohol (R-OH) and an alkyl iodide (R'-I).

Write the products: After the bond cleavage, one product will be an alcohol (R-OH) formed from the group still attached to the oxygen, and the other product will be an alkyl iodide (R'-I) formed from the group that was cleaved.

Verify the stoichiometry: Since one equivalent of HI is used, ensure that only one ether bond is cleaved, resulting in the formation of one molecule of alcohol and one molecule of alkyl iodide as the major products.

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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 in the presence of 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 a bimolecular nucleophilic substitution (SN2) pathway. In this mechanism, the iodide ion acts as a nucleophile, attacking the carbon atom bonded to the ether oxygen after the ether is protonated. Understanding this mechanism is essential for predicting the major products and their formation during the reaction.

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