Cis-trans isomerism is observed in some alkenes but not others. Explain why 1,2-dichloroethene can exist as cis and trans isomers, and predict whether 1,1-dichloroethene can exist as cis and trans isomers, giving a reason for 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)

1,2-dichloroethene has a C=C double bond that cannot rotate, so the groups attached to each carbon are fixed in space. Each carbon of the double bond carries two different groups (Cl and H), giving two distinct spatial arrangements: the Cl atoms can be on the same side (cis) or on opposite sides (trans). Therefore 1,2-dichloroethene can exist as both cis and trans isomers.

In 1,1-dichloroethene one carbon of the double bond has two identical groups (both Cl). Because the two groups on that carbon are identical, there is only one spatial arrangement; cis and trans forms cannot be distinguished. Hence 1,1-dichloroethene cannot exist as cis and trans isomers.

Examiner tips

  • Show the restriction of rotation about the C=C bond first. Mention the different groups on each carbon for 1,2‑dichloroethene. State the two possible arrangements (cis/trans). Explain why 1,1‑dichloroethene lacks two different groups on one carbon and therefore has no stereoisomers.

Common mistakes

  • Forgetting that the double bond cannot rotate. Confusing the identity of the groups on the carbons of 1,1‑dichloroethene (thinking it has two different groups). Writing that 1,1‑dichloroethene can have cis/trans without noting the identical Cl atoms.

Mark scheme (5 marks)

  1. The C=C double bond cannot rotate (freely) / rotation is restricted about the C=C double bond
  2. Each carbon of the double bond in 1,2-dichloroethene has two different groups attached to it
  3. This gives rise to two different spatial arrangements / the groups can be on the same side (cis) or opposite sides (trans)
  4. 1,1-dichloroethene cannot exist as cis and trans isomers
  5. Because one carbon of the double bond in 1,1-dichloroethene has two identical groups (both Cl) attached to it

Key terms in this question

cis-trans isomerism

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