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JEE Main Chemistry question

ChemistryAlcohols, Phenols and EthersJEE Main

How many of the following ethers will produce methyl iodide on treatment with hot concentrated HI? Dimethyl ether, tert-butyl ethyl ether, methyl -propyl ether, ethyl methyl ether, dipropyl ether.

Answer: 3

Solution

Cleavage by hot concentrated HI proceeds by iodide attacking the least hindered alkyl carbon; dimethyl ether, ethyl methyl ether, and methyl -propyl ether all have a methyl group attached to the ether oxygen, which is cleaved

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Question ID VK-149036