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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2:37 minutes

Problem 23

Textbook Question

What are the major products obtained when the following ether is heated with one equivalent of HI?

Verified step by step guidance

Step 1: Analyze the structure of the ether provided. The ether consists of an oxygen atom bonded to two alkyl groups: ethyl (CH₃CH₂-) and isopropyl (CH₃CH(CH₃)-).

Step 2: Understand the reaction mechanism. When an ether is heated with one equivalent of HI, the bond between the oxygen and one of the alkyl groups is cleaved. The cleavage occurs via an SN2 mechanism if the alkyl group is primary or secondary, and via an SN1 mechanism if the alkyl group is tertiary.

Step 3: Determine which bond will break. In this case, the ethyl group is primary, and the isopropyl group is secondary. The bond between the oxygen and the ethyl group is more likely to break due to the SN2 mechanism being favored for primary alkyl groups.

Step 4: Predict the products. The cleavage of the ether will result in the formation of two products: ethyl iodide (CH₃CH₂I) and isopropanol (CH₃CH(CH₃)OH). The ethyl group reacts with the iodide ion (I⁻), while the isopropyl group retains the hydroxyl group (OH).

Step 5: Summarize the reaction. Heating the ether with one equivalent of HI results in the major products ethyl iodide and isopropanol, formed through the cleavage of the ether bond.

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Key Concepts

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

Ethers and Their Reactions

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. When heated with strong acids like HI, ethers undergo cleavage, breaking the C-O bond. This reaction typically results in the formation of alcohols and alkyl halides, depending on the structure of the ether and the conditions of the reaction.

Hydroiodic Acid (HI) as a Cleavage Agent

Hydroiodic acid is a strong acid that can protonate ethers, making them more susceptible to nucleophilic attack. In the presence of HI, the ether is cleaved to yield iodide ions and alcohols. The reactivity of HI facilitates the breaking of the ether bond, leading to the formation of the corresponding alkyl iodide and alcohol.

Mechanism of Ether Cleavage

The mechanism of ether cleavage involves protonation of the ether oxygen, followed by nucleophilic attack by iodide ions. This results in the formation of an alkyl iodide and an alcohol. Understanding this mechanism is crucial for predicting the products of the reaction, as the structure of the ether influences the pathway and the major products formed.

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