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The major products C and D formed in the following reaction respectively are H3C–CH2–CH2–O–C(CH3)3 → excess HI → C + D

1. H3C–CH2–CH2–OH and HO–C(CH3)3
2. H3C–CH2–CH2–I and I–C(CH3)3
3. H3C–CH2–CH2–OH and I–C(CH3)3
4. H3C–CH2–CH2–I and HO–C(CH3)3

Correct answer: H3C–CH2–CH2–I and I–C(CH3)3

Solution

In the reaction of an ether with excess HI, the bond between the oxygen and the less sterically hindered alkyl group breaks, forming alkyl iodides. Here, H3C–CH2–CH2–I and I–C(CH3)3 are the products.

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