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Ppt 7 isomers

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  • 1. Isomers Structural, Geometric, Enantiomer SBI4U
  • 2. Isomers
    • Isomers are compounds that have the same molecular formula but different structures and therefore different chemical properties.
    All three molecules chemical formula is C 6 H 12 O 6 You need to memorize these three molecules
  • 3. Structural Isomer
    • same KIND and AMOUNT of atoms (molecular formula) but the atoms have different connectivity
      • For example, butane and isobutane have the same molecular formula C4H10, but butane has a straight skeleton and isobutane has a branched skeleton.
  • 4. Structural isomers usually have different physical and chemical properties
  • 5. Structural Isomer
    • How many different structures can you make from C 5 H 12 ?
    • How many structural isomers of C 20 H 42
  • 6. Isomers of pentane
  • 7. Structural Isomers
    • C 5 H 12 3
    • C 20 H 42 366,319
    • Structural isomers may also differ in the location of double bonds.
  • 8. Geometric Isomers
    • same molecular formula and the SAME connectivity but different spatial arrangements
    • Different arrangement around a carbon.
    • Due to inflexibility of double bonds
    • Cis (same side) and trans formatio n (across)
  • 9.  
  • 10. Which are geometric isomers and which are structural isomers?
  • 11. Enantiomer
    • molecules that are mirror images of each other
    • Note : left and right hands are a pair of enantiomers (mirror images not identical )
    • non-superimposable mirror image
    • Name other body parts that are enantiomers
  • 12. Enantiomer
    • Requirement: an asymmetric carbon (has 4 different groups bonded to it)
    • Chiral molecule: molecules with an asymmetric carbon such that it has a non-superimposable mirror image
    • Achiral: a molecule that lacks chiral properties
    • A molecule that can exist as a pair of enantiomers has the property of chirality
  • 13. Away from you Towards you
  • 14. Is this a structural, geometric or enantiomer isomer?
  • 15. Enzymes, which themselves are always chiral, often distinguish between the two enantiomers of a chiral substrate . Chiral objects (glove) have different interactions with the two enantiomers of other chiral objects (left and right hand). Analogy: A left hand will not fit into a right-handed glove
  • 16.
    • Even the subtle structural differences in two enantiomers have important functional significance because of emergent properties from the specific arrangements of atoms.
      • One enantiomer of the drug thalidomide reduced morning sickness, its desired effect, but the other isomer caused severe birth defects (teratogenic).
      • administering only one enantiomer will not prevent the teratogenic effect in humans.
      • The body naturally creates the enantiomer.
  • 17. Things to keep in mind…
    • http://2.bp.blogspot.com/_K91FA3B4cpM/SJ_NUmBWWGI/AAAAAAAAACY/UzL8H8Q4oag/s400/ist2_1744503_frustration.jpg
    • Are the molecules identical? If they are, they are not isomers.
    • Always look for structural isomers first (look at C’s)
  • 18. Birth Defects
  • 19. other Enantiomers
    • Other biological processes may be triggered by only one of the two possible enantiomers of a chiral molecule, often being unresponsive to the other enantiomer. For example, S-carvone ("left-handed") is the flavor of caraway, while R-carvone ("right-handed") is the flavor of spearmint.
  • 20. Videoclips
    • http://www.youtube.com/watch?v=MnD-nxtRouc
    • http://www.youtube.com/watch?v=rT48OFFaDwE&feature=related