JEE MainChemistryCarboxylic Acid Derivatives
Consider the following two isomeric carboxylic acids: I. Pentanoic acid II. 2,2-Dimethylpropanoic acid Choose the correct relationship regarding their boiling points and solubilities in water.
Options
- ABoiling point: I > II ; Solubility in water: I > II
- BBoiling point: II > I ; Solubility in water: II > I
- CBoiling point: I > II ; Solubility in water: II > I
- DBoiling point: II > I ; Solubility in water: I > II
Correct answer
C. Boiling point: I > II ; Solubility in water: II > I
Step-by-step solution
Boiling point depends on the surface area of the molecule. Pentanoic acid (I) is a straight-chain isomer with a larger surface area, leading to stronger van der Waals forces and a higher boiling point. 2,2-Dimethylpropanoic acid (II) is highly branched and more spherical, which decreases its surface area and van der Waals forces, resulting in a lower boiling point. Solubility in water depends on the size and shape of the hydrophobic alkyl group. The branched and compact hydrophobic group in II causes less disruptio