Section 1 - Structural, Bonding, and Molecular Properties of Organic Molecules
Section 2 - The Nature of Organic Compounds: Alkanes and Cycloalkanes
Section 3 - Stereochemistry of Alkanes and Cycloalkanes: 3-D Structures of Molecules
Section 4 - The Study of Organic Reactions: An Overview
Section 5 - Structure and Reactivity of Alkenes
Section 6 - Reactions and Synthesis of Alkenes
Section 7 - Alkynes
Section 8 - Stereochemistry - A Detailed Look
Section 9 - Alkyl Halides (R-X)
Section 10 - Substitution (SN2, SN1) and Elimination (E2, E1) Reactions
Section 11 - Mass Spectrometry and IR Spectroscopy
Section 12 - NMR Spectroscopy
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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 about 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
_· “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”)
_· 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)
_· 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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