Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: NMR 1H · Exam: NET JUNE 2011 · Marks: 2 · Difficulty: Hard
An organic compound $\mathrm{A}\left(\mathrm{C}_{8} \mathrm{H}_{16} \mathrm{O}_{2}\right)$ on treatment with an excess of methyl-magnesium chloride generated two alcohols $B$ and $C$, whereas reaction of $A$ with lithium aluminium hydride generated only a single alcohol C. Compound B on treatment with an acid yielded an olefin ( $\mathrm{C}_{6} \mathrm{H}_{12}$ ), which exhibited only a singlet at $\delta=1.6 \mathrm{ppm}$ in the ${ }^{\mathrm{1}} \mathrm{H ~ NMR}$ spectrum. The compound A is: