Isomerism

Isomerism

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Content

• Isomerism: constitutional (structural); cis-trans; enantiomerism

Learning Outcomes

Candidates should be able to:

(a) describe constitutional (structural) isomerism

(b) describe cis-trans isomerism in alkenes, and explain its origin in terms of restricted rotation due to the presence of π bonds [use of E, Z nomenclature is not required]

(c) explain what is meant by a chiral centre

(d) deduce whether a given molecule is chiral based on the presence or absence of chiral centres and/or a plane of symmetry

(e) recognise that an optically active sample rotates plane-polarised light and contains chiral molecules

(f) recognise that enantiomers have identical physical properties except in the direction in which they rotate plane-polarised light [usage of the term diastereomers is not required]

(g) recognise that enantiomers have identical chemical properties except in their interactions with another chiral molecule

(h) recognise that different stereoisomers exhibit different biological properties, for example in drug action

(i) deduce the possible isomers for an organic molecule of known molecular formula

(j) identify chiral centres and/or cis-trans isomerism in a molecule of given structural formula

In each of the sections below, 11.3 to 11.8, candidates will be expected to be able to predict the reaction products of a given compound in reactions that are chemically similar to those specified.