Chirality and Optical Isomerism

chirality

optical isomerism

structural and stereoisomerism

racemic mixture

SN1 and SN2

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CHIRALITY & OPTICAL ACTIVITY
Isomers are compounds with the same molecular formula
STRUCTURAL ISOMERS
Same molecular formula but a
different structural formula
Carbon-chain isomerism is
when isomers have different
length carbon chains due to
branching of molecules
Positional isomerism is when
isomers have the same
functional group, but it is
bonded to different atoms
within the molecule
Functional group isomerism is
when isomers have a different
functional group
STEREOISOMERISM
Same molecular formula but a
different spatial arrangement
Geometric isomerism occurs when there is a C=C group restricting rotation
because of the pi bond. If both C-atoms attached to the C=C group have their
highest Mr group on the same side, then it is described as a cis or Z isomer. If both
C-atoms attached to the C=C group have their highest Mr group on opposite sides,
then it is described as a trans or E isomer.
Optical isomerism is when enantiomers are produced from compounds that are not
symmetrical
OPTICAL ACTIVITY
Chiral carbon atoms have four different atoms or groups attached
Chiral centre gives optical isomers
Optical isomers able to rotate the plane of polarisation of plane polarized
monochromatic light
Each chiral molecule has two optical isomers, which rotate the plane of polarisation
of plane polarized monochromatic light in opposite directions (R and S).
A racemic mixture contains equimolar quantities of the two optical isomers of a
molecule and is optically inactive

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SN1 AND SN2 MECHANISMS
In SN1, the intermediate is
planar, so the nucleophile can
attack either above or below the
plane producing a racemic mixture
In SN2, the nucleophile
attacks from the side
opposite the halogen,
producing a chiral
product that is
optically active…read more

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