But-2-enedioic acid exists as two stereoisomers: maleic acid (cis) and fumaric acid (trans). Explain why but-2-enedioic acid can exist as cis and trans stereoisomers, and explain how the cis and trans forms of but-2-enedioic acid differ from each other in terms of the arrangement of their atoms.

Eduqas A-Level Chemistry — 4.1 Stereoisomerism · Explain · 5 marks · View as Markdown

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

But-2-enedioic acid has the molecular formula C₄H₄O₄ and contains a C=C double bond with a –COOH group attached to each carbon of the double bond.

Model answer (5 marks)

The C=C double bond has a π bond, so rotation about the bond is restricted, giving a fixed arrangement of the groups attached to each sp² carbon.
Each sp² carbon of the double bond is bonded to a –COOH group and to a hydrogen atom, so the two groups on each carbon are different.
Because of the lack of rotation, the two –COOH groups can either be on the same side of the double bond (cis, maleic acid) or on opposite sides (trans, fumaric acid).
In the cis isomer the two –COOH groups lie on the same side of the C=C plane, whereas in the trans isomer they lie on opposite sides.
Thus the two compounds have identical molecular formulas and bond connectivity but differ in the spatial arrangement of the –COOH groups around the double bond.

Examiner tips

  • Show the restriction of rotation about the C=C bond first, then explain the different side‑by‑side or opposite‑side arrangement of the –COOH groups.
  • Use the terms cis (maleic) and trans (fumaric) explicitly and describe the side of the double bond each group occupies.

Common mistakes

  • Confusing the double bond with a single bond and implying rotation is possible.
  • Failing to state that the two isomers have the same formula and connectivity, only different spatial arrangement.

Mark scheme (5 marks)

  1. The C=C double bond does not allow rotation (restricted/no rotation about the double bond)
  2. Each carbon of the double bond has two different groups attached to it
  3. In the cis (maleic acid) form, the two –COOH groups are on the same side of the double bond
  4. In the trans (fumaric acid) form, the two –COOH groups are on opposite sides of the double bond
  5. The two stereoisomers have the same molecular formula and the same bonds/connectivity but different spatial arrangements of atoms

Key terms in this question

stereoisomers

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