Chapter 18, Problem 34P

Compound A has the molecular formula $C_6{H}_{12}{O}_3$ and shows a strong IR absorption peak at 1710 $c{m}^{-1}$. When treated with iodine in aqueous sodium hydroxide, A gives a yellow precipitate. When A is treated with Tollens’ reagent ( $Ag{\left(N{H}_3\right)}_2{}^{+}H{O}^{-}$, a test for an aldehyde or a group that can be hydrolyzed to an aldehyde, Sect. 16.13B), no reaction occurs; however, if A is treated first with water containing a drop of sulfuric acid and then with Tollens’ reagent, a silver mirror (positive Tollens’ test) forms in the test tube. Compound A shows the following 1H NMR spectrum. Write a structure for A.

Singlet $\delta 2.1$

Doublet $\delta 2.6$

Singlet $\delta 3.2\left(6H\right)$

Triplet $\delta 4.7$