Organic chemistry is built entirely on one unusual fact about carbon: its ground-state configuration is 1s22s22p2, four valence electrons short of a stable octet either way, and reaching a noble-gas configuration by simply gaining or losing four electrons (to form C4− or C4+) costs far too much energy to ever happen in practice. So carbon essentially never forms simple ions -- instead, in almost every compound it makes, it forms four covalent bonds.
Those four bonds are explained by hybridisation. During bonding, one electron is promoted from the 2s orbital into the empty 2pz orbital, and the resulting four orbitals mix and rearrange:
- sp3 hybridisation gives four equivalent sigma bonds arranged with tetrahedral geometry -- the default for a carbon making four single bonds.
- sp2 hybridisation leaves one unhybridised p orbital free; the three sp2 orbitals give trigonal planar geometry, and sideways overlap of the leftover p orbitals on two adjacent sp2 carbons forms one pi bond (a C=C double bond, one sigma + one pi).
- sp hybridisation leaves two unhybridised p orbitals free; the two sp orbitals give linear geometry, and sideways overlap of both leftover p orbitals forms two pi bonds (a C≡C triple bond, one sigma + two pi).
Counting pi bonds in a structure is therefore just a matter of counting double and triple bonds: a plain C=C contributes one pi bond; a C=O (as in an aldehyde or ketone carbonyl) also contributes one pi bond; a carboxylic acid's C=O contributes one pi bond (the C-OH bond is a plain sigma bond, not a second pi bond); a C≡C or C≡N contributes two pi bonds. Working out a molecule's hybridisation pattern carbon-by-carbon (sp3 wherever only single bonds meet that carbon, sp2 at each end of a double bond, sp at each end of a triple bond) is one of the most common early exam skills built on this idea.
Because carbon bonds covalently rather than ionically, every organic compound inherits a shared family of physical and chemical hallmarks: they are generally insoluble in polar solvents like water but dissolve readily in organic solvents (benzene, toluene, ether, chloroform); most are flammable (CCl4 is the standard exception) and have comparatively low melting and boiling points, a direct consequence of weak intermolecular forces between covalent molecules; and their chemistry is dominated by their functional group -- almost every reaction an organic compound undergoes happens specifically AT that functional group, regardless of the rest of the molecule. Compounds sharing a functional group typically fall into a homologous series, a run of compounds whose successive members differ by exactly one CH2 unit in molecular formula (methane, ethane, propane... for alkanes), share one general formula (CnH2n+2 for alkanes, CnH2n for alkenes, CnH2n−2 for alkynes and alkadienes alike), can usually be made by the same general preparative methods, show a smooth gradation in physical properties as the chain lengthens, yet behave almost identically in their chemical reactions.