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Lecture

07-19 - Nucleophilic Substitution, Inversion.docx

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Department
Chemistry
Course
CHEM 2OA3
Professor
Jeff Landry
Semester
Winter

Description
Chemical Consequences of Inversion  Retention (invert twice)  Inversion does not necessarily mean R  S  Diastereoisomerization  What makes a good L- (A-)? 1. Ability to accommodate e-pair (charge): e-negativity + resonance 2. Size of the orbital describing the e-pair 3. Indirectly: Bond Strength C-L (H-A)  Fluorine is most electronegative element  Iodine is the best leaving group AND nucleophile (in the Halides) o Increasing size is more important to good leaving group than increasing electronegativity Nucleophilicity “Nu”  Affected by charge, basicity, solvent, polarizability, sterics o Charge (for same atom)  The more charged, the more Nucleophilic o Basicity (decreases to the right in PT, so does Nu)  As expected, trend opposite L ability  Nucleophilicity doesn’t always track with basicity (basicity decreases as you go down the PT, but nucleophilicity increases) o Reason: Solvent effects and polarizability (deformability of orbitals) have a strong influence  Protic Solvent: Solvents with hydrogen attached to electronegative atom (e.g. oxygen) o “Polar”; H O, RO
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