Chapter 16, Problem 16.89P

Three constitutional isomers of molecular formula ${\text{C}}_{\text{5}}{\text{H}}_{\text{8}}\text{O}$ can be converted to 1-pentanol $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}\right)$ on treatment with two equivalents of ${\text{H}}_{\text{2}}$ in the presence of a Pd catalyst. Draw the structures of the three possible compounds, all of which contain a carbonyl group.