Ethene
C2H4Two parallel p orbitals overlap sideways to make the π bond. Its electrons sit above and below the plane, not between the carbons.
- C–C 1.33 Å
- C–H 1.09 Å
- ∠HCH 117°
- ∠CCH 122°
- planar
In ethene (also called ethylene) each carbon bonds to only three atoms: two hydrogens and the other carbon. So each carbon mixes its 2s orbital with just two of its 2p orbitals, making three sp² hybrid orbitals. Those three lie flat in one plane, about 120° apart. They make the C–H bonds and a C–C σ bond.
That leaves one 2p orbital on each carbon, standing straight up and down from the plane. Turn on p orbitals and look edge-on: the two p orbitals sit side by side, parallel, and they overlap sideways. That sideways overlap is the π bond. A double bond is one σ bond plus one π bond.
Now turn on π electrons. The π bond’s electrons sit in two clouds, one above the plane of the atoms and one below, not along the line between the carbons. The faint sheet marks that plane: the π density is exactly zero there. This is the key picture for alkenes: the π electrons are exposed above and below the molecule, which is why alkenes react with electron-seeking reagents.
The π bond also explains two other facts. Ethene is completely flat, because the p orbitals can only overlap if both CH₂ ends lie in the same plane. And the two ends can’t rotate without breaking that overlap, which is why cis and trans isomers of alkenes exist. The C=C bond (about 1.33 Å) is also shorter than ethane’s C–C bond.
Sources
- OpenStax Organic Chemistry, 1.8: sp2 Hybrid Orbitals and the Structure of Ethylene
- OpenStax Chemistry 2e, 8.3: Multiple Bonds
3D structure, measurements and electron clouds computed with PySCF (B3LYP/def2-SVP). Computed values can differ from measured ones by a degree or so, or a few hundredths of an ångström.