Isomerism Flashcards
Isomerism
Occurs when two or more compounds have the same molecular formula but different arrangement of atoms in the molecules
Constitutional (structural) isomerism
Constitutional isomers have the same molecular formula but different connectivity of atoms, meaning that their atoms are connected in a different order.
3 types of constitutional isomerism
chain isomerism
positional isomerism
functional group isomerism
cis-trans isomerism
- Cis-trans isomers arise when there is restricted rotation about a bond or a certain part of a molecule, due to a double bond or a ring structure.
- In alkene, there is restricted rotation of groups joined by C=C bond due to the presence of the π bond.
- For cis-trans isomerism to occur in alkenes, each carbon atom involved in the double bond must have 2 different groups bonded to it (cis-trans isomerism is not possible if one carbon atom of the double bond bears two identical groups)
Cis-trans isomerism is also possible due to the restricted rotation about bonds in ring structures.
There must be at least two substituent groups bonded to the ring.
Enantiomerism
Enantiomers arise when the molecule is asymmetric, i.e. when it does not have a plane of symmetry
(or centre of symmetry).
A plane of symmetry is defined as an imaginary plane through the molecule that divides it into two
halves, where each half is an exact reflection of the other half. This plane may pass through atoms,
between atoms (bonds), or both. Such a molecule is described as chiral.