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Ch. 8 - Elimination ReactionsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Sections
E2 Mechanism
Beta Hydrogen
E2 - Anti-Coplanar Requirement
E2 - Cumulative Practice
E1 Reaction
Solvents
Leaving Groups
Nucleophiles and Basicity
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
Cumulative Substitution/Elimination

Time to discuss the most complicated mechanism of the bunch, E2. It’s an awesome reaction, but there are a few extra details we’re gonna have to keep track of!

Concept #1: Drawing the E2 Mechanism.

Summary: A negatively charged nucleophile reacts with an inaccessible leaving group to produce beta-elimination in one-step.

Concept #2: Understanding the properties of E2.

Properties of E2 reactions:

  • Nucleophile =  Strong
  • Leaving Group =  Substituted
  • Reaction coordinate = Transition State
  • Reaction = Concerted
  • Rate =  Bimolecular
  • Rate =  k[Nu][RX]
  • Stereochemistry = Anti-Coplanar

Example #1: Rank the following alkyl halides in order of reactivity toward E2 reaction.