Chapter 14, Problem 7RAT

Explain why caprylic acid, ${\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{6}}\text{COOH}$, dissolves in a $5\%$ aqueous solution of sodium hydroxide but caprylaldehyde, ${\text{CH}}_{\text{3}}{\left({\text{CH}}_{\text{2}}\right)}_{\text{6}}\text{CHO}$, does not dissolve.

(a) With two oxygens, the caprylic acid is about twice as polar as the caprylaldehyde.

(b) The caprylaldehyde is a gas at room temperature.

(c) The caprylaldehyde behaves as a reducing agent, which neutralizes the sodium hydroxide.

(d) The caprylic acid reacts to form the water-soluble salt.