Shapes of organic molecules; σ and π bonds

AS Level Chemistry · An introduction to AS Level organic chemistry. A short explanation of the idea, the rules to remember, the mistake to avoid, a worked example and practice questions with answers.

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The idea

Carbon chains can be straight, branched or cyclic (joined in a ring). The shape around each carbon atom depends on how its orbitals are mixed, which is called hybridisation.

A σ bond forms when two orbitals overlap end-on, directly between the two nuclei. Every single bond is a σ bond. A π bond forms when two p orbitals overlap sideways, above and below the line between the nuclei. A double bond is one σ and one π bond; a triple bond is one σ and two π bonds.

Count the atoms joined to a carbon atom: four means sp3, three means sp2, two means sp. A planar molecule, such as ethene, has all its atoms in one plane.

Rules to remember

Common mistake

Students often count a double bond as two π bonds, or forget the C–H bonds. Every bond contains exactly one σ bond, and each C–H bond must be counted too.

Worked example

How many σ bonds and π bonds are there in propyne, CH3C≡CH, and what is the hybridisation of each carbon atom from left to right?

  1. C–H bonds: 3 in CH3 and 1 at the other end = 4 σ bonds.
  2. Carbon–carbon: the C–C single bond is 1 σ; the C≡C triple bond is 1 σ + 2 π.
  3. Totals: 4 + 1 + 1 = 6 σ bonds and 2 π bonds.
  4. The CH3 carbon is joined to four atoms (sp3); each carbon of the triple bond is joined to two atoms (sp).

Answer: 6 σ bonds and 2 π bonds; hybridisation sp3, sp, sp.

Practice questions

Try each one, then open the answer.

1. How many σ and π bonds are there in propene, CH3CH=CH2?

  1. A
    8 σ and 1 π
  2. B
    9 σ and 0 π
  3. C
    7 σ and 2 π
  4. D
    8 σ and 2 π
Show answer

Answer: A. Propene has six C–H bonds, one C–C single bond and one C=C double bond. Every bond contains one σ bond, giving 6 + 1 + 1 = 8 σ bonds, and the second bond of the C=C is the single π bond.

2. Which compound has a branched carbon chain?

  1. A
    hexane
  2. B
    cyclohexane
  3. C
    hex-1-ene
  4. D
    2-methylpentane
Show answer

Answer: D. 2-methylpentane has a methyl side-chain on C2 of a five-carbon chain. Hexane and hex-1-ene are straight chains, and cyclohexane is cyclic.

3. What is the H–C–H bond angle in ethene?

  1. A
    109.5°
  2. B
    180°
  3. C
    120°
  4. D
    107°
Show answer

Answer: C. Each carbon in ethene is sp2 hybridised with three regions of electron density in a plane, giving angles of about 120°. The tetrahedral 109.5° applies to sp3 carbons such as those in ethane.

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