Chapter 22, Problem 22.8P

Deduce the structures of compounds $A$ and $B$, two of the major components of jasmine oil, from the given data.

Compound $A$: ${\text{C}}_{\text{9}}{\text{H}}_{\text{10}}{\text{O}}_{\text{2}}$; IR absorptions at $\text{3091}-\text{2895}$ and ${\text{1743 cm}}^{-1}$; $\text{1H}$ NMR signals at $2.06$ (singlet, $\text{3 H}$), $5.08$ (singlet, $\text{2 H}$), and $7.33$ (broad singlet, $\text{5 H}$ ) $\text{ppm}$.

Compound $B$: ${\text{C}}_{14}{\text{H}}_{\text{12}}{\text{O}}_{\text{2}}$; IR absorptions at $3091-2953$ and ${\text{1718 cm}}^{-1}$; $\text{1H}$ NMR signals at $5.35$ (singlet, $\text{2 H}$ ) and $7.26-8.15$ (multiplets, $\text{10 H}$) $\text{ppm}$.