Stereoisomerism is the occurrence of compounds with the same molecular formula but different spatial arrangements, affecting drug action and activity.
- Stereoisomerism is a form of isomerism in which molecules have:
- The same molecular formula
- The same sequence of bonded atoms (i.e., the same structural formula)
- But a different spatial arrangement of atoms or groups in 3D space
- So, unlike structural (constitutional) isomers, stereoisomers differ only in how atoms are oriented in space, not in how they’re connected.
Classification of Stereoisomerism
-
Geometrical Isomerism (cis-trans or E/Z)
- Occurs due to restricted rotation (e.g., around double bonds or in cyclic systems)
- Groups are arranged differently in space relative to a reference plane
- Examples:
- Cis-but-2-ene (same groups on the same side)
- Trans-but-2-ene (same groups on opposite sides)
- E/Z isomerism in alkenes with different substituents
-
Optical Isomerism
- Arises due to the presence of chiral centers or asymmetry
- Molecules that can rotate plane-polarized light
- Based on the concept of chirality
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