Cis-trans isomerism is a type of stereoisomerism. Explain what is meant by the term stereoisomers and describe the structural feature required for a molecule to show cis-trans isomerism. Use 2-bromobutene as an example to illustrate your answer.

WJEC A-Level Chemistry (Wales) — 4.1 Stereoisomerism · Explain · 5 marks · View as Markdown

Written & reviewed by James Millett — Biology (Imperial College London), PGCE Science (University of Cambridge).

Model answer (5 marks)

Stereoisomers are compounds that have the same molecular formula, the same atoms bonded in the same order and the same structural formula but differ in the spatial arrangement of their atoms.

Cis‑trans isomerism occurs when a C=C double bond is present. The double bond restricts rotation, so the groups attached to each sp² carbon cannot freely rotate.

For cis‑trans isomerism each carbon of the double bond must bear two different groups. In 2‑bromobutene the double bond is between C2 and C3. C2 is bonded to H and Br, while C3 is bonded to H and CH₃. Because each carbon has two different substituents, the molecule can exist as a cis isomer (Br and CH₃ on the same side) and a trans isomer (Br and CH₃ on opposite sides).

Examiner tips

  • Define stereoisomers first, then explain the spatial difference. Show the double bond restriction and the requirement of two different groups on each double‑bond carbon. Use the 2‑bromobutene example to illustrate the groups on each carbon and the cis/trans arrangement.

Common mistakes

  • Confusing stereoisomers with structural isomers. Forgetting to mention the double bond restriction. Not recognising that each double‑bond carbon must have two different substituents.

Mark scheme (5 marks)

  1. Stereoisomers have the same molecular formula / same atoms bonded in the same order / same structural formula
  2. But stereoisomers differ in the arrangement / orientation of atoms in space
  3. A C=C double bond is required (restricted rotation around the double bond)
  4. Each carbon of the double bond must have two different groups / atoms attached to it
  5. Correct use of 2-bromobutene: identifies that the two carbons of the C=C each bear two different groups (e.g. one carbon has H and Br; the other has H and CH3 / ethyl group), allowing cis (same side) and trans (opposite sides) isomers

Key terms in this question

stereoisomers · cis-trans isomerism

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