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This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

Isomerism. University of Lincoln presentation. This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License. Isomerism. ISOMERS are compounds with the same molecular formula (but different arrangements of atoms).

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  1. Isomerism University of Lincoln presentation This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  2. Isomerism ISOMERS are compounds with the same molecular formula (but different arrangements of atoms) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  3. Types of Isomerism • Structural isomerism • Stereoisomerism • Geometric (cis/trans) • Optical This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  4. 1. Structural isomerism This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  5. Structural Isomerism C2H6O ethanol methoxymethane These two compounds are structural isomers This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  6. Structural Isomerism o– p– m– –nitromethylbenzene Structural isomers often have different chemical & physical properties This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  7. Exercise Q What two compounds, with different functional groups, are isomers with the formula: C3H6O2 This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  8. Answer A carboxylic acid An ester This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  9. 2. Stereoisomerism a. Geometric isomerism This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  10. Geometric Isomerism (cis/trans) If two compounds have the same formulae and the same structural framework, but differ in the spatial arrangement of different atoms or groups about a central atom This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  11. Geometric Isomerism (cis/trans) or about a double bond, This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  12. Geometric Isomerism (cis/trans) then the compounds are called GEOMETRIC ISOMERS • Cis–on the same side • Trans–on the opposite side This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  13. Geometric Isomerism (cis/trans) [Pt(NH3)2Cl2] Cis–diamminedichloroplatinum(II) Trans–diamminedichloroplatinum(II) This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  14. Geometric Isomerism (cis/trans) There is restricted rotation about a C=C double bond and the two isomers are not inter-convertible without first breaking the C=C bond Cis-but-2-ene Trans-but-2-ene This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  15. Geometric isomerism helps you see! 11-cis-retinal 11-trans-retinal 11 12 R R’ R’ 11 12 R Cis Trans This reaction is the central feature of human vision This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  16. 2. Stereoisomerism b. Optical isomerism This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  17. Optical Isomerism Optical isomerism is caused by a lack of symmetry in a molecule’s structure so that the molecule and its mirror image are actually different –like a left hand and a right hand: They are non-superimposable This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  18. For example Optical isomers are called ENANTIOMERS Nonsuperimposable mirror images This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  19. Enantiomers Labels L– and D– are given to two enantiomers to distinguish them from each other Only one optical isomer of DOPA called L-DOPA, is effective in the treatment of Parkinson’s disease This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  20. Asymmetric Carbon A compound that is NOT SUPERIMPOSABLE on its mirror image is described as being CHIRAL Many chiral compounds contain an asymmetric carbon atom – a carbon atom with FOUR different groups attached This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  21. CHIRAL Carbon This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  22. For example – limonene Lemons Oranges This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  23. For example – limonene CHIRAL C Lemons Oranges This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

  24. Acknowledgements • JISC • HEA • Centre for Educational Research and Development • School of natural and applied sciences • School of Journalism • SirenFM • http://tango.freedesktop.org This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

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