Arrange in decreasing order of boiling points: Pentanal, Pentanoic acid, 2-Methylbutan-1-ol.
Boiling points: Pentanoic acid (strong H-bonding) > 2-Methylbutan-1-ol (H-bonding) > Pentanal (dipole-dipole).
Ref: NCERT Class 12 Chemistry > Chapter 12: Aldehydes, Ketones and Carboxylic Acids > Topic: Chemical Reactions - Reduction, Oxidation and Tests - Tollens, Fehling, Iodoform