Section 10 - Substitution (SN2, SN1) and Elimination (E2, E1) Reactions
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Substitution and Elimination Reactions - Section 10 of Organic Chemistry Notes is 21 pages in length (page 10-1 through page 10-21) and covers ALL you'll need to know on the following lecture/book topics:
SECTION 10 - Substitution (SN1, SN2) and Elimination (E1, E2) Reactions
10-1 -- Overview of Nucleophilic Substitutions and Eliminations
· SN2 Reaction
· SN1 Reaction
· E2 Reaction
· E1 Reaction
10-1 -- The SN2 Reaction
· Bimolecular, Nucleophilic, Substitution
· Stereochemistry
· “Back-side Displacement” and Inversion of Absolute Configuration
· Effect of Alkyl Halide Structure (1°, 2°, 3°)
· Branching at the Beta-Carbon (β-Carbon)
· Nucleophilicity and its Dependence on the Solvent
· Steric Bulk Considerations
· Leaving Groups (l.g.’s)
· The Tosylate Leaving Group (-OTs, or p-toluenesulfonate)
· Intramolecular SN2 Reactions
10-9 -- The E2 Reaction
· Bimolecular Elimination; Beta-Elimination (β-Elimination)
· Stereochemistry of the E2 Reaction
· C-H and C-X = Periplanar
· Syn-Periplanar vs. Anti-Periplanar
· Regiochemistry Concerns
· Multiple β-H’s
· Zaitsev’s Rule
· Small Bases vs. Large Bulky Bases
· Cyclic Systems (Rings) and the E2 Reaction
· The E2 Reaction and Cyclohexane Chair Conformations
10-14 -- Competition Between SN2 and E2 Reactions
· 3° Halides, 2° Halides, and 1° Halides
10-15 -- E2 Elimination of Vinyl Halides
· Converting Alkenes to Alkynes
10-16 -- SN1 and E1 Reactions
· Unimolecular Reactions (First-Order)
· Ionization of the Alkyl Halide (R-X)
· The Rate-Determining Step (“Rate-Limiting Step”)
· Solvolysis
· Ionization Step in Detail
· Best Leaving Groups
· Formation of Allylic and Benzylic Carbocations
· Alkyl Substitution and Carbocation Stability
· Solvent Effects on the SN1 / E1 Ionization Step
· Polar or Non-Polar Solvents?
· The Dielectric Constant (Є)
· Product Determining Step(s)
· Carbocations
· SN1 Stereochemistry
· E1 Regiochemistry and Zaitsev’s Rule
10-21 -- SN2 vs. E2 vs. SN1/E1
· When are SN2 and E2 Favored?
· Is There a Good Leaving Group (l.g)?
· Is There a Good Nucleophile Present?
· When are SN1 and E1 Favored?
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