Answer to Question #132084 in Organic Chemistry for Thomas

Question

Which compound in each pair is more water soluble? Which compound in each pair is more soluble in an organic solvent?

(a) CH3CH2CH2CH3 or CH3CH2CH2CH2CO2H

(b) CH3(CH2)4COOH or CH3(CH2)4COO–Na+.

Answer 1

(a) CH₃CH₂CH₂CH₃ is more soluble in non-polar organic solvents because it is also non-polar. CH₃CH₂CH₂CH₂CO₂H is more soluble in water than CH₃CH₂CH₂CH₃.

(b) CH₃(CH₂)₄COOH is more soluble in organic solvents. CH₃(CH₂)₄COO^–Na⁺ is more soluble in water because of its ionic nature.