Which one of the following ether gives methanol as one of the product when heated with conc. HI

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answer is C.

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Detailed Solution

Mixed ethers (containing 1° (or) 2° alkyl groups) when heated with conc. HI give an alkyl halide in which the halogen atom is attached to smaller alkyl group. The mechanism is SN2.(1) C2H5OH+CH3I (2) (CH3)2CHOH+CH3IMixed ethers (containing 3° alkyl group or benzyl (or) allyl groups) when heated with conc. HI give an alkyl halide (or) allyl halide (or) benzyl halide in which halogen atom is attached to more stable carbocation. The mechanism is SN1 (3) (CH3)3C-I+CH3OHC6H5-O bond cannot be cleaved .Due to resonance C6H5-O bond acquires double bond character.

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