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Organic Chemistry

Topic 3 of 34

Hybrid orbitals form the sigma framework; unhybridised p orbitals form pi bonding

The local bonding pattern predicts tetrahedral, planar or linear geometry.

A-Level 9476 (2026-2027)

Hybrid orbitals form the sigma framework; unhybridised p orbitals form pi bonding

The local bonding pattern predicts tetrahedral, planar or linear geometry.

The four specified carbon frameworks
MoleculeCarbon hybridisation and shapeCarbon-carbon bonding
EthaneEach C uses four sp3 orbitals; tetrahedral, approximately 109.5°.One sigma bond from end-on overlap. Rotation is possible without breaking the sigma bond.
EtheneEach C uses three coplanar sp2 orbitals; trigonal planar, approximately 120°.One sigma bond plus one pi bond from sideways overlap of parallel unhybridised p orbitals.
BenzeneEach C is sp2 and the ring is planar, approximately 120°.A sigma framework and a delocalised pi system from all six parallel p orbitals; all C-C bonds are equivalent.
EthyneEach C uses two sp orbitals; linear, 180°.One sigma bond and two pi bonds formed by two perpendicular sets of p orbitals.

Hybridisation is a bonding model: one s and three p orbitals combine into four sp3 orbitals, one s and two p into three sp2, or one s and one p into two sp orbitals. The remaining p orbitals are available for π overlap. Count regions of σ bonding around an atom; a double bond still points in one direction in the molecular framework.

Worked example

Transfer the model to an unfamiliar molecule

Predict local geometry in CH3CH=CHCN.

  1. The CH3 carbon has four sigma bonds and is approximately tetrahedral.
  2. Each C=C carbon has three sigma-bond directions and is approximately trigonal planar.
  3. The nitrile carbon has two sigma-bond directions, one to carbon and one within C≡N; it is approximately linear.
  4. The alkene pi orbitals must remain parallel, explaining restricted rotation about C=C.
Answer

Approximately 109.5° around CH3, 120° around the alkene carbons and 180° at the nitrile carbon. Geometry is local; a molecule need not have one hybridisation throughout.