JEE MAIN - Chemistry (2025 - 4th April Morning Shift - No. 15)
An organic compound $(\mathrm{X})$ with molecular formula $\mathrm{C}_3 \mathrm{H}_6 \mathrm{O}$ is not readily oxidised. On reduction it gives $\mathrm{C}_3 \mathrm{H}_8 \mathrm{O}(\mathrm{Y})$ which reacts with HBr to give a bromide $(\mathrm{Z})$ which is converted to Grignard reagent. This Grignard reagent on reaction with $(\mathrm{X})$ followed by hydrolysis give 2,3-dimethylbutan-2-ol. Compounds $(\mathrm{X}),(\mathrm{Y})$ and $(\mathrm{Z})$ respectively are:
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHO}, \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH}, \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{Br}$
$\mathrm{CH}_3 \mathrm{COCH}_3, \mathrm{CH}_3 \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_3, \mathrm{CH}_3 \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_3$
$\mathrm{CH}_3 \mathrm{COCH}_3, \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{OH}, \mathrm{CH}_3 \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_3$
$\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHO}, \mathrm{CH}_3 \mathrm{CH}=\mathrm{CH}_2, \mathrm{CH}_3 \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_3$
Explanation
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