Ketone - Structure and Properties

Structure and Properties

The ketone carbon is often described as "sp2 hybridized," a description that includes both their electronic and molecular structure. Ketones are trigonal planar around the ketonic carbon, with C-C-O and C-C-C bond angles of approximately 120°. Ketones differ from aldehydes in that the carbonyl group (CO) is bonded to two carbons within a carbon skeleton. In aldehydes, the carbonyl is bonded to one carbon and one hydrogen and are located at the ends of carbon chains. Ketones are also distinct from other carbonyl-containing functional groups, such as carboxylic acids, esters and amides.

The carbonyl group is polar as a consequence of the fact that the electronegativity of the oxygen is greater than that for carbon. Thus, ketones are nucleophilic at oxygen and electrophilic at carbon. Because the carbonyl group interacts with water by hydrogen bonding, ketones are typically more soluble in water than the related methylene compounds. Ketones are hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and cannot hydrogen-bond to itself. Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are more volatile than alcohols and carboxylic acids of comparable molecular weights. These factors relate to pervasiveness of ketones in perfumery and as solvents.