Ether Cleavage
Ether cleavage by HI proceeds to give:
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About This Question
- Subject
- chemistry
- Chapter
- oxygen organics
- Topic
- ether cleavage
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Alcohol and alkyl iodide
- Step 1: The Ether oxygen is protonated by the strong acid HI building a dialkyl oxonium ion.
- Step 2 (SN2/SN1): The Iodide ion (I−), being a good nucleophile, attacks the less sterically hindered carbon (if SN2) or the one forming a stable carbocation (if SN1).
- Bond Breaking: This results in the cleavage of the C−O bond on one side.
- Fragments: The products are an Alkyl Iodide and an Alcohol.
- Excess Conditions: If HI is in excess and heated, the resulting alcohol can further react to form a second molecule of alkyl iodide.
This medium difficulty chemistry question is from the chapter oxygen organics, covering the topic of ether cleavage. It appeared in the 2025 exam.
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