Chapter 18, Problem 33P

(a) A compound U $\left(C_9{H}_{10}O\right)$ gives a negative iodoform test. The IR spectrum of U shows a strong absorption peak at 1690 $c{m}^{-1}$. The ${}^{1}H$ NMR spectrum of U gives the following data. What is the structure of U?

Triplet $\delta 1.2\left(3H\right)$

Quartet $\delta 3.0\left(2H\right)$

Multiplet $\delta 7.7\left(5H\right)$

(b) A compound V is an isomer of U. Compound V gives a positive iodoform test; its IR spectrum shows a strong peak at 1705 $c{m}^{-1}$. The ${}^{1}H$ NMR spectrum of V gives the following data. What is the structure of V?

Singlet $\delta 2.0\left(3H\right)$

Singlet $\delta 3.5\left(2H\right)$

Multiplet $\delta 7.1\left(5H\right)$