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9476 / 2027
Organic Chemistry

Lesson 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)

  • I can describe carbon hybridisation in the reference molecules.Syllabus

    Syllabus 9476, 11.1(b). Describe carbon hybridisation in the reference molecules.

  • I can explain the reference molecular shapes and bond angles.Syllabus

    Syllabus 9476, 11.1(c). Explain the reference molecular shapes and bond angles.

  • I can predict shape and angles in analogous molecules.Syllabus

    Syllabus 9476, 11.1(d). Predict shape and angles in analogous molecules.

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 model of bonding. One s and three p orbitals combine to make four sp3 orbitals. One s and two p orbitals make three sp2 orbitals. One s and one p orbital make two sp orbitals. Any p orbitals left over can overlap sideways to form π bonds. To decide the shape, count the regions of σ bonding around an atom. A double bond still counts as one direction.

Worked exampleTransfer the model to an unfamiliar molecule

Predict local geometry in CH3CH=CHCN.

Try it first. Then show the worked stepsHide the worked steps
  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.

Check your understanding

What is the hybridisation and shape around each carbon in ethyne, HC≡CH?

  1. sp, linear at 180 degrees, with one sigma and two pi bonds in C≡C
  2. sp2, trigonal planar at 120 degrees, with one sigma and one pi bond
  3. sp3, tetrahedral at 109.5 degrees, with three sigma bonds in C≡C
Show the answer

sp, linear at 180 degrees, with one sigma and two pi bonds in C≡C

Each carbon has two regions of sigma bonding, so it uses two sp orbitals and is linear. The two unhybridised p orbitals on each carbon overlap sideways to give two pi bonds.