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Mathematical Skills in Chemistry

Chiral centres, E/Z isomerism and optical activity

  • 3 things to know
  • Components 01, 02 and 03

Overview

Recall questions on identifying a chiral centre, the condition for E/Z isomerism, how optical isomers differ, and why a racemic mixture does not rotate light.

What you need to know

Answer each one before you reveal it.

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Process

In a three-dimensional structural representation, what do a solid wedge and a dashed line indicate?

Process

What structural feature is required for a molecule to show E/Z isomerism?

Process

Which of but-1-ene and but-2-ene shows E/Z isomerism, and why?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    In a three-dimensional structural representation, what do a solid wedge and a dashed line indicate?

    Model answer

    A solid wedge shows a bond pointing out of the plane of the paper towards the viewer, and a dashed line shows a bond pointing behind the plane of the paper.

  2. 2

    What is a chiral centre, and how is one identified in a structure?

    Model answer

    It is a carbon atom carrying four different groups, identified by checking each of the four attached groups and confirming that no two are the same.

  3. 3

    Does 2-hydroxypropanoic acid, CH₃CH(OH)COOH, contain a chiral centre? Justify your answer.

    Model answer

    Yes, because the middle carbon carries four different groups: H, OH, CH₃ and COOH.

  4. 4

    Does propan-2-ol contain a chiral centre? Justify your answer.

    Model answer

    No, because the central carbon carries two identical methyl groups as well as H and OH, so only three different groups are attached.

  5. 5

    What structural feature is required for a molecule to show E/Z isomerism?

    Model answer

    There must be restricted rotation about a C=C double bond, and each of the two carbon atoms of that bond must carry two different groups.

  6. 6

    Which of but-1-ene and but-2-ene shows E/Z isomerism, and why?

    Model answer

    But-2-ene does, because each double-bonded carbon carries a methyl group and a hydrogen; but-1-ene does not, because one of its double-bonded carbons carries two hydrogen atoms.

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