Aldehyde

An aldehyde /ˈældᵻhaɪd/ or alkanal is an organic compound containing a formyl group. The formyl group is a functional group, with the structure R-CHO, consisting of a carbonyl center (a carbon double bonded to oxygen) bonded to hydrogen and an R group, which is any generic alkyl or side chain. The group without R is called the aldehyde group or formyl group. Aldehydes differ from ketones in that the carbonyl is placed at the end of a carbon skeleton rather than between two carbon atoms. Aldehydes are common in organic chemistry. Many fragrances are aldehydes.

Structure and bonding

Aldehydes feature an sp²-hybridized, planar carbon center that is connected by a double bond to oxygen and a single bond to hydrogen. The C-H bond is not acidic. Because of resonance stabilization of the conjugate base, an α-hydrogen in an aldehyde (not shown in the picture above) is far more acidic, with a pKa near 17, than a C-H bond in a typical alkane (pKa about 50). This acidification is attributed to (i) the electron-withdrawing quality of the formyl center and (ii) the fact that the conjugate base, an enolate anion, delocalizes its negative charge. Related to (i), the aldehyde group is somewhat polar.