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Substitution and elimination reactions

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Free radical reactions
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Nucleophilicity (nucleophile strength)Nucleophilicity vs. basicity
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E2 reactionsE1 reactionsZaitsev's rule
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Comparing E2, E1, Sn2, Sn1 reactionsE2 E1 Sn2 Sn1 reactions example 2E2 E1 Sn2 Sn1 reactions example 3
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Identifying nucleophilic and electrophilic centersCurly arrow conventions in organic chemistryIntro to organic mechanismsAlkyl halide nomenclature and classificationSn1 mechanism: kinetics and substrateSn1 mechanism: stereochemistryCarbocation stability and rearrangement introductionCarbocation rearrangement practiceSn1 mechanism: carbocation rearrangementSn1 carbocation rearrangement (advanced)Sn2 mechanism: kinetics and substrateSn2 mechanism: stereospecificitySn1 and Sn2: leaving groupSn1 vs Sn2: Solvent effectsSn1 vs Sn2: Summary
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E1 mechanism: kinetics and substrateE1 elimination: regioselectivityE1 mechanism: stereoselectivityE1 mechanism: carbocations and rearrangementsE2 mechanism: kinetics and substrateE2 mechanism: regioselectivityE2 elimination: StereoselectivityE2 elimination: StereospecificityE2 elimination: Substituted cyclohexanesRegioselectivity, stereoselectivity, and stereospecificity
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Elimination vs substitution: reagentElimination vs substitution: primary substrateElimination vs substitution: secondary substrateElimination vs substitution: tertiary substrate

About this unit

Sn1, Sn2, E1, and E2 reactions form the basis for understanding why certain products are more likely to form than others. We will learn about the reaction mechanisms, and how nucleophilicity and electrophilicity can be used to choose between different reaction pathways.