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Structural Isomerism 1 butane 2-methylpropane C4H10.

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Presentation on theme: "Structural Isomerism 1 butane 2-methylpropane C4H10."— Presentation transcript:

1 Structural Isomerism 1 butane 2-methylpropane C4H10

2 Structural isomerism 2 propan-1-ol propan-2-ol C3H8O

3 Structural isomerism 3 butanoic acid ethyl ethanoate C4H8O2

4 Geometric isomerism trans 2-butene cis 2-butene

5 Optical isomerism R-2-butanol S-2-butanol

6 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.

7 Crystals of tartaric acid (K+ / NH4+ salt)

8 Production of polarised light

9 Perpendicular polarising crystals

10 Importance of optical isomerism
S-thalidomide (teratogen) R-thalidomide (sedative)

11 The Sn2 Mechanism C R1 R3 R2 Cl

12 C R1 R3 R2 Cl O- H

13 Cl ( )- R2 R1 C R3 O H

14 Cl- R1 R2 R3 C O H

15 Cl- R1 R2 R3 C O H

16 Cl- R1 R2 R3 C O H

17 Cl- R1 R2 R3 C O H

18 Cl- R1 R2 R3 C O H

19 Cl- R1 R2 R3 C O H

20 Cl- R1 R2 R3 C O H

21 Cl- R1 R2 R3 C O H

22 Cl- R1 R2 R3 C O H

23 Cl- R1 R2 R3 C O H

24 Cl- R1 R2 R3 C O H

25 Cl- R1 R2 R3 C O H

26 C R1 R3 R2 Cl Sn2 Reactant R1 R3 R2 O H C Product Sn1

27 C R1 R3 R2 Cl Sn2 Reactant R1 R3 R2 O H C Product Sn1

28                                                                                         Figure 5 - Action of a sheet of Polaroid on unpolarised light

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