substitution-cont - 2 O Solvent What is the difference...

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Substitution continued.
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What about the other substitution reaction? Why the observed rates? (consideration of the substrate)
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Formation of the carbocation is rate-limiting • More highly substituted carbocations are more stable Why? Induction:
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Hyperconjugation What?
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Stabilities
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Nucleophile Not important
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Leaving group Important, but they are easy to select (or predict): Look at the pK a of the conjugate acid -OTos > I > Br > Cl > H
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Unformatted text preview: 2 O Solvent What is the difference between the S N 2 and the S N 1 reactions? The intermediate is positive in the S N 1 case whereas the transition state is dispersed and negative in the S N 2 reaction. Polar, protic solvents work well with S N 1 reactions Examples (often solvolysis reactions) The Stereochemistry of S N 1: Sometimes, a little inversion is observed:...
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This note was uploaded on 03/24/2009 for the course CHEMISTRY 030.205 taught by Professor Greenberg during the Fall '08 term at Johns Hopkins.

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substitution-cont - 2 O Solvent What is the difference...

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