Formic acid is one of the main irritants in ant and bee stings,
and acetic acid is familiar in vinegar. Propionic acid, which is
porduced by certain strains of bacteria, is responsible for the
characteristic odor and taste of Swiss cheese, and butyric acid
causes the smell of rancid butter. Caproic acid has a ripe goat
smell. Valeric acid has the odor that we associate with Limburger
cheese and manure, although it first was extracted from the root
of the valerian or heliotrope plant. It once was considered medicinally
valuable as a sedative, but it is not clear whether its value was
physiological or psychological, in terms of the threat of a second
dose.
Because one hydrogen atom in a carboxylic acid is attached to the
more electronegative oxygen atom rather than to a carbon, these
acids are polar and capable of forming extensive hydrogen-bonded
networks. They are acids because this same proton dissociates in
aqueous solution (right). The explanation of the ready dissociation
is similar to that for carbonic acid and phenol. In undissociated
acid the proton is bound to one oxygen, and a double bond extends
from the carbon to the other oxygen. In the carboxyl ion the electrons
of that double bond and the formerly bonding electron pair of the
departed proton all are delocalized throughout the entire O-C-O
group. This delocalization stabilizes the ion and shifts the equilibrium
in favour of dissociation.