Chapter 15, Problem 53P

Propose a structure consistent with each set of data.

a. Compound A:

$\begin{array}{l}\text{Molecular}\text{formula:}{\text{C}}_{\text{8}}{\text{H}}_{\text{10}}\text{O}\\ \text{IR}\text{absorptions}\text{at}\text{3150-2850,}{\text{cm}}^{-\text{1}}\\ {}^1\text{H}\text{NMR}\text{data:}\text{1}\text{.4}\left(\text{triplet,}\text{3}\text{H}\right),3.9\text{5}\left(\text{quartet,}\text{2}\text{H}\right),\\ \text{and}6.8-7.\text{3}\left(\text{multiplet,}\text{5}\text{H}\right)\text{ppm}\end{array}$

b. Compound B:

$\begin{array}{l}\text{Molecular}\text{formula:}{\text{C}}_9{\text{H}}_{\text{10}}{\text{O}}_2\\ \text{IR}\text{absorptions}\text{at}\text{1669}{\text{cm}}^{-\text{1}}\\ {}^1\text{H}\text{NMR}\text{data:}\text{2}\text{.5}\left(\text{singlet,}\text{3}\text{H}\right),3.8\left(\text{singlet,}\text{3}\text{H}\right),6.9\left(\text{doublet,}2\text{H}\right),\\ \text{and}7.9\left(\text{doublet,}2\text{H}\right)\text{ppm}\end{array}$