Question
Explain the hybridisation of carbon in ethane (), ethene (), and ethyne (). State the geometry, bond angles, and bond lengths in each case.
Solution — Step by Step
In ethane (), each carbon is bonded to 3 H atoms and 1 C atom — total 4 bonds, no lone pairs on carbon.
Hybridisation: — the 2s orbital mixes with all three 2p orbitals to form four equivalent hybrid orbitals.
Each orbital overlaps with one H (sigma bond), and the two carbons form a C–C sigma bond by – overlap.
- Geometry: Tetrahedral around each carbon
- Bond angle: H–C–H = 109.5°
- C–C bond length: 154 pm (single bond, longest)
- Bond type: Only sigma () bonds
In ethene (), each carbon forms a double bond with the other carbon and two sigma bonds with H atoms — 3 groups around each carbon.
Hybridisation: — the 2s mixes with only TWO of the three 2p orbitals to form three hybrid orbitals. One p orbital remains unhybridised.
The three orbitals form:
- 2 sigma bonds with H atoms
- 1 sigma bond with the other carbon (– overlap)
The two unhybridised p orbitals (one on each carbon, perpendicular to the molecular plane) overlap laterally to form a pi () bond.
- Geometry: Trigonal planar around each carbon
- Bond angle: H–C–H ≈ 120°
- C=C bond length: 134 pm (shorter than single bond — pi bond pulls carbons closer)
- Bond type: One + one in the C=C bond
In ethyne (), each carbon forms a triple bond with the other carbon and one sigma bond with H — 2 groups around each carbon.
Hybridisation: — the 2s mixes with only ONE 2p orbital to form two hybrid orbitals. Two p orbitals remain unhybridised.
The two orbitals form:
- 1 sigma bond with H
- 1 sigma bond with the other carbon
The four unhybridised p orbitals (two per carbon, perpendicular to each other) form two pi bonds — creating the triple bond.
- Geometry: Linear around each carbon
- Bond angle: H–C–C = 180°
- C≡C bond length: 120 pm (shortest — two pi bonds pull carbons very close)
- Bond type: One + two in the C≡C bond
| Property | Ethane () | Ethene () | Ethyne () |
|---|---|---|---|
| Hybridisation | |||
| Geometry | Tetrahedral | Trigonal planar | Linear |
| Bond angle | 109.5° | 120° | 180° |
| C–C bond | Single (154 pm) | Double (134 pm) | Triple (120 pm) |
| Pi bonds | 0 | 1 | 2 |
| s-character | 25% | 33% | 50% |
Why This Works
As we go from to to , the percentage of s-character in the hybrid orbital increases: 25% → 33% → 50%. Greater s-character means the electrons are held closer to the nucleus (s orbitals are closer to nucleus than p). This results in:
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Shorter, stronger bonds — C≡C is shorter and stronger than C=C, which is shorter and stronger than C–C.
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Greater acidity of terminal H — In ethyne, the terminal C–H bond has 50% s-character, making the carbon very electronegative. The H is slightly more acidic (can be removed by strong bases). This is why ethyne reacts with sodium (forms sodium acetylide) but ethane doesn’t.
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Bond angles increase — More p-character in the hybrid = more p-like (90° preferred angle). More s-character pushes angles toward 180°.
Alternative Method — Count Groups, Assign Hybridisation
Quick rule: count the number of groups around the carbon (bonds + lone pairs on carbon):
- 4 groups →
- 3 groups →
- 2 groups →
For ethane C: 4 bonds, 0 lone pairs = 4 groups → . For ethene C: 2 single + 1 double = 3 groups → . For ethyne C: 1 single + 1 triple = 2 groups → .
Common Mistake
Saying ethene has 4 bonds per carbon and should be . Counting individual bond lines: C in ethene has 2 C–H bonds and 1 C=C bond. Count the double bond as ONE group (not two). So 3 groups → . Similarly in ethyne: 1 C–H and 1 C≡C = 2 groups → . Always count groups (sigma bonds + lone pairs), not electron pairs in pi bonds.