Chapter 14, Problem 14.73P

Propose a structure consistent with each set of data.

a. A compound X (molecular formula ${\text{C}}_6{\text{H}}_{\text{12}}{\text{O}}_2$) gives a strong peak in its IR spectrum at $1740{\text{cm}}^{-1}$. The ${}^1\text{H}\text{NMR}$ spectrum of X shows only two singlets, including one at $\text{3}\text{.5}\text{ppm}$. The ${}^{13}\text{C}\text{NMR}$ spectrum is given below. Propose a structure for X.

b. A compound Y (molecular formula ${\text{C}}_6{\text{H}}_{\text{10}}$) gives four lines in its ${}^{13}\text{C}\text{NMR}$ spectrum ( $27,30,67$, and $93\text{ppm}$), and the IR spectrum given here. Propose a structure for Y.