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Published byPenelope Warner Modified over 6 years ago
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Structural Isomerism 1 butane 2-methylpropane C4H10
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Structural isomerism 2 propan-1-ol propan-2-ol C3H8O
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Structural isomerism 3 butanoic acid ethyl ethanoate C4H8O2
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Geometric isomerism trans 2-butene cis 2-butene
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Optical isomerism R-2-butanol S-2-butanol
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Optical isomerism An optical isomer (enantiomer) molecule is non-superimposable on its mirror image. A carbon atom with 4 different groups attached to it gives rise to optical isomerism and is said to be chiral. A solution of an enantiomer rotates the plane of plane polarised light. Enantiomers of a molecule have identical m.p. and b.p. A 1:1 mixture of opposite sense enantiomers is called a racemic mixture and a solution of it has no effect on the plane of plane polarised light.
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Crystals of tartaric acid (K+ / NH4+ salt)
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Production of polarised light
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Perpendicular polarising crystals
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Importance of optical isomerism
S-thalidomide (teratogen) R-thalidomide (sedative)
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The Sn2 Mechanism C R1 R3 R2 Cl
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C R1 R3 R2 Cl O- H
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Cl ( )- R2 R1 C R3 O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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Cl- R1 R2 R3 C O H
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C R1 R3 R2 Cl Sn2 Reactant R1 R3 R2 O H C Product Sn1
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C R1 R3 R2 Cl Sn2 Reactant R1 R3 R2 O H C Product Sn1
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Figure 5 - Action of a sheet of Polaroid on unpolarised light
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