Identify the product formed when aryl-alkyl ether reacts with cold HI.
Show Hint
- alkyl iodide and water
- aryl iodide and water
- alkyl iodide, aryl iodide and water
- phenol and alkyl iodide
The Correct Option is D
Solution and Explanation
The oxygen of the ether picks up a proton from HI to form an oxonium ion.
Step 2: Attack of iodide
Iodide attacks the less hindered alkyl carbon and releases the phenol as the leaving group.
Step 3: Result
Cold HI stops at this stage, since the phenol does not react further to give an aryl iodide.
Final Answer:
Phenol and the alkyl iodide are formed. \[ \boxed{\text{(D) }\text{phenol and alkyl iodide}} \]
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IUPAC name of the given ether is:
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Replacement of a hydrogen atom in a hydrocarbon by an alkoxy or carboxyl group yields a class of compounds known as ethers. Ethers are classified as symmetrical or unsymmetrical on the basis of groups attached to the oxygen atoms. Diethyl ether, a symmetrical ether, has been widely used as an inhalation anesthetic. Ethers can be prepared by acid catalyzed intermolecular dehydration of alcohols and Williamson's synthesis. Acid catalyzed dehydration of alcohols is not generally preferred as it gives a mixture of elimination and substitution products. In Williamson's synthesis, an alkyl halide is allowed to react with sodium alkoxide. Ethers containing substituted Alkyl groups may also be prepared by this method. The C-O bond in ether is weakly polar and is cleaved under drastic conditions with excess of hydrogen halides. In electrophilic substitution, the alkoxy group deactivates the aromatic ring and directs the incoming group to ortho and para positions.
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