JEE Main Chemistry question

Chemistry Haloalkanes and Haloarenes JEE Main

Compound A, when treated with ethyl magnesium iodide in dry ether, forms an addition compound which on hydrolysis forms compound B. The compound B on oxidation forms 3-pentanone. Hence, the compound A and B are

(A)Propanal, pentanolCorrect
(B)Ethanal, pentanol
(C)Acetone, 3-pentanol
(D)None of these

Answer: (A)

Solution

3-Pentanone, CH₃CH₂COCH₂CH₃, comes from oxidation of the secondary alcohol 3-pentanol (B), CH₃CH₂CH(OH)CH₂CH₃. Working backward, B (3-pentanol, with an ethyl group on each side of the carbinol carbon) is

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Question ID VK-149423