Question:
Identify the product formed when aryl-alkyl ether reacts with cold HI.
Identify the product formed when aryl-alkyl ether reacts with cold HI.
Show Hint
The alkyl-oxygen bond breaks, while the aryl-oxygen bond is stronger and stays intact.
Updated On: Nov 12, 2026
- alkyl iodide and water
- aryl iodide and water
- alkyl iodide, aryl iodide and water
- phenol and alkyl iodide
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The Correct Option is D
Solution and Explanation
Step 1: Understanding the Concept
Ethers are cleaved by HI through protonation of the oxygen followed by attack of iodide on the alkyl group.
Step 2: Aryl alkyl ether
\(\text{Ar-O-R}+\text{HI}\rightarrow\text{Ar-OH}+\text{R-I}\)
Step 3: Why not aryl iodide
The \(\text{C}_\text{aryl}-\text{O}\) bond has partial double bond character because of resonance, and the iodide cannot attack an sp2 carbon of the ring.
Final Answer:
The products are phenol and an alkyl iodide. \[ \boxed{\text{(D) }\text{phenol and alkyl iodide}} \]
Ethers are cleaved by HI through protonation of the oxygen followed by attack of iodide on the alkyl group.
Step 2: Aryl alkyl ether
\(\text{Ar-O-R}+\text{HI}\rightarrow\text{Ar-OH}+\text{R-I}\)
Step 3: Why not aryl iodide
The \(\text{C}_\text{aryl}-\text{O}\) bond has partial double bond character because of resonance, and the iodide cannot attack an sp2 carbon of the ring.
Final Answer:
The products are phenol and an alkyl iodide. \[ \boxed{\text{(D) }\text{phenol and alkyl iodide}} \]
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