Chapter7 - Chapter 7 Further Reactions of Haloalkanes Just...

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Chapter 7 – Further Reactions of Haloalkanes Just when you thought it was over… 1
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Solvolysis We learned that S N 2 reaction rates diminish going from primary to secondary to tertiary carbons at the reacting center. These kinds of carbons do undergo reactions – but of the unimolecular flavor. The observations in Table 7-1 tell you that the mechanism of this reaction must be different from that of bimolecular substitution reactions, where the trend of reaction at a more substituted carbon center is slower than at a less substituted one. 2
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Mechanism Stereochemistry, kinetics, ELECTRONICS AND STERICS! The rate equation reflects the species involved in the rate determining step. This is such an important concept in chemistry that we often refer to this as the RDS. Let’s take a bit of time now over a piece of chalk and a blackboard to talk about the RDS and its relationship to activation barriers. 3
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4
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Graphical Depiction of Cation formation 5
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Stereochemical Consequences of Mechanism The transition state in a S N 1 substitution reaction contains an sp 2 hybridized achiral, planar carbocation. Therefore, in general a chiral center will be racemized by this process. But… 6
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Leaving Group, Solvent and Nucleophile The rate limiting step in the S N
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