Substitution-part1 - Substitution and Elimination Reactions...

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Substitution and Elimination Reactions
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All of the possibilities
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The Kinetics of the Bimolecular Substitution Reaction (S N 2):
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That transition state
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If nucleophile and leaving group are not the same:
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What is the HOMO/LUMO Interaction?
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Inversion of configuration:
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What if the substrate is chiral?
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Consideration of the factors: • Substrate • Nucleophile Leaving group • Solvent
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What prevents this reaction from occurring?
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Substrate in S N 2 Reactions 0 (CH 3 ) 3 CBr 8.3 x 10 -4 (CH 3 ) 2 CHBr 3 x 10 -2 CH 3 CH 2 Br 1 CH 3 Br Substrate relative rate CN + RBr RCN + Br Alpha branching– branching at the carbon with the leaving group
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What about branching next to the carbon? ß-Branching: 10 -5 0.03 1 Relative Rate Substrate Br Br Br Br C C C H H H H H H H H H N C
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Trends in cyclic systems: Br Br Br Br Br Relative rates 1 10 -4 10 -3 1.6 10 -2
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That transition state is? And the path to the backside must be unobstructed (and in cyclohexane, those axial hydrogens get in the way)
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Other substrates Br Br CN sp 2 transition state Why the reaction rate is slightly faster than methyl: 1.6 vs 1 in relative rates
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2. Nucleophile
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