2-Bromobut-2-ene can exist as cis and trans stereoisomers. Explain why 2-bromobut-2-ene can form cis and trans isomers, and describe how the cis and trans isomers of 2-bromobut-2-ene differ from each other.
Written & reviewed by James Millett — Biology (Imperial College London), PGCE Science (University of Cambridge).
2-Bromobut-2-ene has the molecular formula C₄H₇Br and contains a carbon–carbon double bond.
Model answer (5 marks)
2‑Bromobut‑2‑ene contains a C=C double bond, so rotation about the bond is restricted.
Each sp² carbon of the double bond is bonded to two different groups – a methyl group and a hydrogen on one carbon, and a bromine and a propyl group on the other.
Because of the lack of rotation, the relative positions of the two larger groups (methyl and propyl) are fixed. If the two larger groups are on the same side of the double bond, the molecule is the cis isomer; if they are on opposite sides, it is the trans isomer.
Thus the cis and trans isomers differ in the spatial arrangement of the larger substituents across the double bond, giving distinct physical and chemical properties.
Each sp² carbon of the double bond is bonded to two different groups – a methyl group and a hydrogen on one carbon, and a bromine and a propyl group on the other.
Because of the lack of rotation, the relative positions of the two larger groups (methyl and propyl) are fixed. If the two larger groups are on the same side of the double bond, the molecule is the cis isomer; if they are on opposite sides, it is the trans isomer.
Thus the cis and trans isomers differ in the spatial arrangement of the larger substituents across the double bond, giving distinct physical and chemical properties.
Examiner tips
- Show the double bond and explain restricted rotation; list the two different groups on each double‑bond carbon; describe the cis/trans arrangement using the larger groups; keep answer concise to fit 5 marks.
Common mistakes
- Confusing the groups that must be compared (e.g. using hydrogens instead of the larger groups); failing to mention the double bond; not recognising that each double‑bond carbon has two different groups.
Mark scheme (5 marks)
- The molecule contains a carbon–carbon double bond (C=C)
- There is no free rotation about the carbon–carbon double bond
- Each carbon of the double bond has two different groups attached to it
- In the cis isomer, the two identical/similar groups (e.g. the two methyl groups or the two larger groups) are on the same side of the double bond
- In the trans isomer, the two identical/similar groups are on opposite sides of the double bond
Key terms in this question
Related
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- Decode the mark scheme abbreviations →
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