Chapter 16, Problem 49P

Compounds W and X are isomers; they have the molecular formula $C_9{H}_{8}O$. The IR spectrum of each compound shows a strong absorption band near $1715c{m}^{-1}$. Oxidation of either compound with hot, basic potassium permanganate followed by acidification yields phthalic acid. The ${}^{1}H$ NMR spectrum of W shows a multiplet at $\delta$ 7.3 and a singlet at $\delta$ 3.4. The 1h NMR spectrum of X shows a multiplet at $\delta$ 7.5, a triplet at $\delta$ 3.1, and a triplet at $\delta$ 2.5. Propose structures for W and X.