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H3C−CH2−CH(OH)−CH3 (i) NaI, H3PO4 (ii) Mg, Dry ether (iii) D2O Product [X] formed in the above reaction is :

1. (1) H3C−CH2−C(H)(OH)−CH3
2. (2) H3C−CH=CH−CH3
3. (3) H3C−CH2−CH(D)−CH3
4. (4) H3C−CH2−CH=CH2

Correct answer: (3) H3C−CH2−CH(D)−CH3

Solution

The correct option (3) H3C−CH2−CH(D)−CH3 is formed because the reaction sequence involves the conversion of the alcohol group to a leaving group, followed by a reaction with magnesium to form a Grignard reagent, which then reacts with deuterium oxide (D2O) to introduce a deuterium atom at the carbon adjacent to the original alcohol, resulting in the product with deuterium substitution.

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