PROCHIRALITY
Prochirality
Prochirality
Pro prochiral Prochiral Chiral
Prochiral centre
Nicotinamide adenine dinucleotide (NADH)
Homomorphic groups/ligands/atoms
■ Homomorphic ligands are indistinguishable when considered in isolation
■ Examples
– Two hydrogen atoms or two bromine atoms
– Groups must have same constitution and configuration
– two methyl or phenyl groups
– Two secondary butyl groups of same chirality (R/S)
Topicity
■ Describes geometrical or stereochemical relationships between
homomorphic atoms/groups/ligands in a molecule
Homotopic ligands
Stereoheterotopic ligands
Enantiotopic ligands Diastereotopic ligands
How to determine topicity of ligands?
Two methods
Symmetry criterion Addition/substitution criterion
Homotopic ligands
Homomorphic ligands in identical environment:
Addition/substitution criterion
Same molecule
Homotopic ligands
Symmetry criterion
Homorphic ligands are homotopic if they can interchange their positions by rotation
about a simple axis
CH2Cl2, CHCl3,
Homotopic ligands
Symmetry criterion
Homotopic ligands
Addition/substitution criterion
Homotopic ligands
Addition/substitution criterion
Homotopic faces
Two faces of a double bond are homotopic if addition to either face generates
identical molecule
Homotopic faces
Ethylene has homotopic faces
Stereoheterotopic ligands/faces ligands
The spatial relation of homomorphic ligands with the rest of molecule is different,
they are termed as stereoheterotopic
Enantiotopic ligands/faces
Symmetry criterion
Enantiotopic ligands /faces are interchangeable by σ plane, centre of symmetry or
alternating axis of symmetry, but cannot be interchanged by simple axis of rotation
Enantiotopic ligands/faces
Symmetry criterion
Enantiotopic Homotopic Enantiotopic
Enantiotopic ligands
Substitution-addition criteria
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Enantiotopic ligands
Pro-R and Pro-S
Pro-R
Pro-S
Enantiotopic faces
Diastereotopic ligands/faces
Diastereotopic ligands/faces
Diastereotopic ligands/faces
Stereochemistry of chemical reactions
Stereochemistry of Addition Reactions
Stereochemistry of bromine addition
Stereochemistry of bromine addition
Anti-addition
Stereochemistry of bromine addition
Syn-addition
Stereochemistry of hydrogenation reaction
Syn-addition
Conformational Isomerism
Conformational isomerism
Open chain alkane conformations: Staggered, eclipsed, and gauche conformers.
Conformational isomerism
Chair and boat conformers in cyclic molecules.
Conformational isomerism
Atropisomerism: A molecule can become chiral due to restricted rotation about a
bond.
Dihedral angle
The angle created by two intersecting planes.
Stability of conformers
Angle strain
The increase in potential energy of a molecule due to bond angles deviating from
the ideal values
Torsional strain
Torsional strain or eclipsing strain is the increase in potential energy of a molecule
due to repulsion between electrons in bonds that do not share an atom
Steric strain
Repulsive interactions between non-bonded atoms in close proximity