Further organic chemistry: Chirality -4

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  • Created by: Shannon
  • Created on: 07-04-15 09:18
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  • Chirality & Isomerism
    • Isomerism
      • Structural
        • Same molecular formula but atoms are arranged differently
      • Stereoisomers
        • Same molecular formula and atoms are arranged in the same way. The difference is the orientation of the bonds
        • E/Z happens because there is no rotation around a double bond
          • Atoms given priority
          • Z = same
          • E = opposite
      • Optical
        • Non super imposable mirror images
    • Chirality
      • Optical isomers occur because of chiral centres
      • A chiral carbon is on that has 4 different groups attached to it
      • Optical isomers are optically active
        • Rotate the plane of polarised light
          • One enantiomer rotates it clockwise, the other anticlockwise
      • Racemic mixture
        • 50/50 mix of both enantiomers
        • Does not show optical activity as the two enantiomers cancel each other out
      • Optical activity to work out a reaction mechanism
        • SN1
          • Produces a racemic mixture
          • Step 1: Group breaks off, leaving a planar ion
          • Step 2: nucleophile can approach from either side of planar ion
        • SN2
          • Produces 1 enantiomer
          • Nucleophile attacks from opposite side to leaving group (steric hinderance) - inversion of stereochemistry

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