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Question

Reaction of Grignard reagent, C2H5MgBr with C8H8O followed by hydrolysis gives compound ''A'' which reacts instantly with Lucas reagent to give compound B, C10H13Cl.
Compound (B) is

A
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B
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C
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D
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Solution

The correct option is A
The reaction of alcohol with Lucas reagent (conc. HCl+anhyd. ZnCl2) is mostly SN1 reaction and the rate of reaction is directly proportional to the stability of carbocation formed in the reaction.
Since, 3o alcohol forms 3o carbocation (most stable) hence, it will react fastest by SN1 reaction to give tertiary halide.

Thus, compound (A) is a tertiary alcohol.
Since C2H5MgBr with C8H8O followed by hydrolysis gives tertiary alcohol, the starting compound is a keto compound.
Hence, with help of molecular formula, the above reaction is given below:


Hence, option (a) is correct.

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