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Section 10 - Substitution (SN2, SN1) and Elimination (E2, E1) Reactions

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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