Chemistry – Organic chemistry | e-Consult

Boiling Point: Ethanethioic acid has a higher boiling point than ethanoic acid. This is because the C-S bond is weaker than the C-O bond in ethanoic acid. Weaker intermolecular forces (specifically, weaker Van der Waals forces) result in a lower boiling point. The weaker C-S bond also means that ethanethioic acid is more prone to dissociation, which can also contribute to a higher boiling point compared to the non-dissociating ethanoic acid.

Solubility: Ethanoic acid is more soluble in water than ethanethioic acid. This is because ethanoic acid can form hydrogen bonds with water, whereas ethanethioic acid cannot. The sulfur atom is less electronegative than oxygen, so the C-S bond is less polar, and therefore, ethanethioic acid cannot effectively donate hydrogen bonds to water. The weaker intermolecular forces in ethanethioic acid also contribute to its lower solubility.

Reactivity: Ethanoic acid is generally more reactive than ethanethioic acid. The C-O bond in ethanoic acid is stronger than the C-S bond in ethanethioic acid. The C-S bond is more susceptible to cleavage, particularly under oxidizing conditions. Ethanoic acid undergoes typical reactions of carboxylic acids, such as esterification and amide formation, more readily than ethanethioic acid.