Carboxylic Acids

• Like any carbonyl compound, its stereochemistry makes it susceptible to nucleophiles.
• On the MCAT, look for carboxylic acid to behave as an acid or as the substrate in  a nucleophilic substitution reaction 
• It is a very strong organic acid, adn the conjugate base is stabilized by resonance. Electron withdrawing groups on the alpha carbon help to further stabilize the conjugate base and thus increase the acidity of the corresponding carboxylic acid.
• Carboxylic acids are able to make strong double hydrogen bonds to form a dimer, which in turn significantly increases the boiling point of carboxylic acids by effectively doubling the molecular weight of the molecules leaving the liquid phase.
• The double bonds in unsaturated carboxylic acids impede the crystal lattice and lower melting point.
• carboxylic acids with 4 or less carbons: miscible with water; with 5 or more: increasingly less soluble in water; 10 or more: insoluble in water.
• carboxylic acids are soluble in most nonpolar solvents because the dimer form allows the carboxylic acid to solvate without disrupting the hydrogen bonds of the dimer.