Chapter 12C, Problem 68P

Reaction of aldehyde $D$ with amino alcohol $E$ in the presence of $\text{NaH}$ forms $F$ (molecular formula ${\text{C}}_{\text{11}}{\text{H}}_{\text{15}}{\text{NO}}_{\text{2}}$). F absorbs at $1730{\text{cm}}^{-1}$ in its IR spectrum. $F$ also shows eight lines in its ${}^{13}\text{C}\text{NMR}$ spectrum, and gives the following ${}^1\text{H}\text{NMR}$ spectrum: $\text{2}\text{.32}\left(\sin \text{glet}6\text{H}\right)\text{,}\text{3}\text{.05}\left(\text{triplet,}2\text{H}\right)\text{,}\text{4}\text{.20}\left(\text{triplet,}2\text{H}\right),\text{6}\text{.97}\left(\text{doublet,}2\text{H}\right),$ $7.82\left(\text{doublet,}2\text{H}\right)$ and $\text{9}\text{.97}\left(\text{singlet,}1\text{H}\right)\text{ppm}$. Propose a structure for F. We will learn about this reaction in Chapter 18.

$\text{D}$ $\text{E}$