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Organic Chemistry I

Stereoisomerism and E/Z nomenclature

  • 3 things to know
  • Papers 2 and 3

Overview

Stereoisomerism and why restricted rotation about C=C gives E/Z isomers, assigning E and Z by Cahn-Ingold-Prelog priority, when cis-trans naming is used instead and how cis and trans isomers differ, identifying chiral centres for optical activity, and using symmetry to describe stereoisomerism.

What you need to know

Answer each one before you reveal it.

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Key term

What is the key structural difference between cis and trans isomers regarding the position of identical groups?

Key term

Define stereoisomerism.

Key term

What is E/Z isomerism?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Define stereoisomerism.

    Model answer

    When compounds have the same structural formula but a different arrangement of atoms in space.

  2. 2

    What is E/Z isomerism?

    Model answer

    A type of stereoisomerism that occurs due to restricted rotation around a carbon-carbon double bond.

  3. 3

    What structural requirement must be met for E/Z isomerism to occur?

    Model answer

    Each carbon of the double bond must have two different groups attached.

  4. 4

    How is priority assigned to groups in E/Z nomenclature?

    Model answer

    Using the Cahn-Ingold-Prelog rules, based on the atomic number of atoms directly attached to the double bond carbons.

  5. 5

    In E/Z nomenclature, what does the Z isomer indicate about the positions of higher priority groups?

    Model answer

    The higher priority groups are on the same side of the double bond (zusammen means together).

  6. 6

    What arrangement of higher priority groups defines the E isomer?

    Model answer

    The higher priority groups are on opposite sides of the double bond (entgegen means opposite).

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