Chapter6Summary - SN2 Inversion of configuration Concerted...

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CHEM 3053 Fall 2011 L. D. Shirtcliff Chapter 6 Summary Nucleophiles - Solvent effects on halides - Strengths of nucleophiles Anionic vs. neutral basicity for same nucleophilic atom - Bases vs. nucleophiles - polarizability Leaving groups - I, Br, Cl, OTs, OTf etc. - Correlation to basicity - What makes a good leaving - What makes a poor leaving group - Comparison of leaving group ability Solvents: - What are dielectric constants - Polar protic - H 2 O, EtOH, MeOH etc. - Polar aprotic - DMF, DMSO, Acetone, Acetonitrile etc. - Solvation - Role that solvents play in SN1, SN2, E1, E2 - How they interact with nucleophiles Carbocations - Stability (1° < 2° < 3°) Mechanisms - SN1 - SN2 - E1 - E2 - Mechanism for neutral vs. anionic nucleophile
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Unformatted text preview: SN2 - Inversion of configuration - Concerted reaction mechanism - Methyl, 1°, 2° - Solvents effects on reaction - Conditions that favor S N 2 SN1 - 3° - Carbocation intermediate - Loss of configuration - Racemization - Solvolysis - Conditions that favor S N 1 E2 - Concerted reaction mechanism - Base strength - Base size - Conditions that favor E2 E1 - Carbocation intermediate - Solvolysis - Conditions that favor E1 Determination of reaction mechanism - SN1 vs. SN2 vs. E1 vs. E2 (Summary Table 6.7 and handouts) - Which mechanism gives what types of products Elimination - Dehydrohalogenation - Alpha and Beta Functional Group Interconversion - Figure 6.11 - Synthesis of compounds from alkyl halides and nucleophiles...
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