Chapter 22, Problem 22.65P

Acid-catalyzed hydrolysis of ${\text{HOCH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{C}{\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{CN}$ forms compound A ( ${\text{C}}_{\text{6}}{\text{H}}_{\text{10}}{\text{O}}_{\text{2}}$). A shows a strong peak in its IR spectrum at $1770{\text{cm}}^{-1}$ and the following signals in its ${}^{\text{1}}\text{H}$ NMR spectrum: $1.27$ (singlet, $\text{6}\text{H}$), $2.12$ (triplet, $\text{2}\text{H}$), and $4.26$ (triplet, $\text{2}\text{H}$) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.