carbon–carbon double bond consists of a sigma bond and a pi bond. This double bond is stronger than a single covalent bond (611 kJ/mol for C=C vs. 347 kJ/mol for C–C), but not twice as strong. Double bonds are shorter than single bonds with an average bond length of 1.33 Å (133 pm) vs 1.53 Å for a typical C-C single bond. Each carbon atom of the double bond uses its three sp2 hybrid orbitals to form sigma bonds to three atoms (the other carbon atom and two hydrogen atoms). The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by the axes of the three sp² hybrid orbitals, combine to form the pi bond. This bond lies outside the main C–C axis, with half of the bond on one side of the molecule and a half on the other. With a strength of 65 kcal/mol, the pi bond is significantly weaker than the sigma bond. Rotation about the carbon–carbon double bond is restricted because it incurs an energetic cost to break the alignment of the p orbitals on the two carbon atoms. Consequently cis or trans isomers interconvert so slowly that they can be freely handled at ambient conditions without isomerization. More complex alkenes may be named with the E–Z notation for molecules with three or four different substituents (side groups). For example, of the isomers of butene, the two methyl groups of (Z)-but-2-ene (a.k.a. cis-2-butene) appear on the same side of the double bond, and in (E)-but-2-ene (a.k.a. trans-2-butene) the methyl groups appear on opposite sides. These two isomers of butene have distinct properties. Shape As predicted by the VSEPR model of electron pair repulsion, the molecular geometry of alkenes includes bond angles about each carbon atom in a double bond of about 120°. The angle may vary because of steric strain introduced by nonbonded interactions between functional groups attached to the carbon atoms of the double bond. For example, the C–C–C bond angle in propylene is 123.9°. For bridged alkenes, Bredt's rule states that a double bond cannot occur at the bridgehead of a bridged ring system unless the rings are large enough. Following Fawcett and defining S as the total number of non-bridgehead atoms in the rings, bicyclic systems require S ≥ 7 for stability and tricyclic systems require S ≥ 11. Physical properties Many of the physical properties of alkenes and alkanes are