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Organic chemistry - Chapter 1: Isomerism - Nam Phan

CONFORMATIONAL ISOMERS
Different shapes of the same molecule resulting
rom rotation around a single C-C bond
Conformational isomers are not different
compounds 
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  1. REFERENCES [1] Nam T. S. Phan, Hoa T. V. Tran ‘Organic chemistry’, VNU-HCMC Publisher, 2011 [2] Nam T. S. Phan, ‘Study guide to organic chemistry’, VNU-HCMC Publisher, 2011 [3] Paula Y. Bruice, ‘Organic chemistry’, fifth edition, Pearson Prentice Hall, 2007 [4] Francis A. Carey, ‘Organic chemistry’, fifth edition, McGraw-Hill, 2003 [5] Paula Y. Bruice, ‘Study guide and solutions manual - Organic chemistry’, fifth edition, Pearson Prentice Hall, 2007 [6] Graham T.W. Solomons, Craig B. Fryhle, ‘Organic chemistry’, eighth edition, John Wiley & Sons, 2004 2
  2. Chapter 1: ISOMERISM Isomers: Compounds with the same molecular formula but different structural formulas Isomers Constitutional isomers Stereoisomers Conformational isomers Configurational isomers Optical isomers /Enantiomers & Geometric isomers Diastereoisomers 4
  3. STEREOISOMERS Isomers that differ in the way their atoms are arranged in space Conformational isomers Configurational isomers 6
  4. Conformations of butane 10
  5. Cahn-Ingold-Prelog priority rules Rule 1 Rule 2 18
  6. OPTICAL ISOMERS A chiral opbject Nonsuperimposable mirror image An achiral object 20
  7. Optically inactive Optically active 22
  8. Isomers with one asymmetric carbon Nonsuperimposable mirror-image molecules are called enantiomers 24
  9. Drawing enantiomers Using Fisher Projection formulas: • Carbon chain is drawn along the vertical line Convention • Vertical lines: bonds going into the page • Horizontal lines: bonds coming out of the page 26
  10. D-L system is only useful for naming sugars & aminoacids 32
  11. Meso compounds 36
  12. Enantiomers vs diastereoisomers • Enantiomers normally have identical physical & chemical properties • Enantiomers normally interact differently with other chiral molecules • Diastereoisomers can have different physical & chemical properties • Enantiomers are always chiral • Diastereoisomers can be chiral or achiral (meso compounds) 38
  13. CHIRALITY & BIOLOGICAL ACTIVITY 40