Chapter 14, Problem 14.57P

Treatment of $2-\text{methylpropanenitrile}\left[{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CHCN}\right]$ with ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{MgBr}$, followed by aqueous

acid, affords compound V, which has molecular formula ${\text{C}}_7{\text{H}}_{\text{14}}\text{O}$. V has a strong absorption in its IR

spectrum at ${\text{1713 cm}}^{-1}$ and gives the following ${}^{\text{1}}\text{H}$ NMR data:

$0.91\left(\text{triplet, 3H}\right)\text{, 1}\text{.09}\left(\text{doublet, 6H}\right)\text{, 1}\text{.6}\left(\text{multiplet, 2H}\right)\text{, 2}\text{.43}\left(\text{triplet, 2H}\right)\text{,}$ and $\text{2}\text{.60}\left(\text{septet, 1H}\right)\text{ppm}$.

What is the structure of V? We will learn about this reaction in Chapter 22.