AP® Chemistry · Unit 2 · Topic 2.2
Bond Order, Length, and Energy
Bond order is the number of shared electron pairs between two atoms. More shared pairs pull the nuclei closer together and take more energy to pull apart, so higher bond order means shorter, stronger bonds between a given pair of atoms.
A single bond is one sigma bond: one pair of electrons shared directly between the nuclei. A double bond adds a π bond, a second pair of electrons shared in a region above and below the sigma bond. A triple bond adds a third pair, another π bond perpendicular to the first. Each extra shared pair pulls more electron density into the space between the two nuclei. That extra negative charge pulls both positive nuclei inward, shortening the distance between them. It also takes more energy to separate the atoms, because you have to break every one of those shared pairs to pull them apart. So going from a single to a double to a triple bond between the same two atoms, the bond gets shorter and the bond energy goes up.
Carbon-carbon bonds show this cleanly. Ethane (CH3-CH3) has a C-C single bond, about 154 pm long, with a bond energy near 347 kJ/mol. Ethene (CH2=CH2) has a C=C double bond, shorter at about 134 pm and stronger at about 614 kJ/mol. Ethyne (CH≡CH, acetylene) has a C≡C triple bond, shorter still at about 120 pm and stronger at about 839 kJ/mol. Same two atoms, three different bond orders, a clean trend in both directions.
That trend only holds when you keep the elements fixed. Compare bonds between different elements and length stops predicting strength reliably, because things like lone-pair repulsion change the picture. This sets up why bond order also predicts bond angles and molecular shape later: more electron pairs crowded around a central atom push neighboring groups farther apart, which is where structure and geometry pick up the story.
Key terms
- Bond order
- The number of shared electron pairs between two bonded atoms, counting sigma and π bonds together.
- Sigma bond
- A bond formed by electron density shared directly along the axis connecting two nuclei.
- π bond
- A bond formed by electron density shared in regions above and below the line connecting two nuclei, present only in double and triple bonds.
- Bond energy
- The energy required to break one mole of a given bond, usually measured in kJ/mol.
- Antibonding orbital
- A molecular orbital that, when occupied, weakens and lengthens the bond between two atoms.
Watch it explained
- How it worksHow does adding a second pair of shared electrons pull the two nuclei closer?
- Worked exampleCompare the bond lengths and energies in ethane, ethene, and ethyne.
- Common mistakeWhy isn't a longer bond always a weaker bond when you compare two different elements?
- Going furtherWhat happens to the bond length when a nitrogen molecule gains an extra electron?
Check yourself
End of topic.