Ch. 8 - Elimination ReactionsSee 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

Solution: One of the stereoisomers below undergoes E2 reactions in the presence of a stong base MUCH faster than the other. (Selecting the correct isomer is not enough to earn points on this question! Your explanation should be sufficiently clear and complete that the reader/grader is left with no doubt that you understand.) Construct both the chair and its flipped conformer for the two stereoisomers below Determine which stereoisomer will have the faster rate of reaction:           a)         or         b) Explain this observation mechanistically using full sentences making sure to answer the question of WHY one will undergo an E2 reaction faster than the other.

Problem

One of the stereoisomers below undergoes E2 reactions in the presence of a stong base MUCH faster than the other. (Selecting the correct isomer is not enough to earn points on this question! Your explanation should be sufficiently clear and complete that the reader/grader is left with no doubt that you understand.)

  1. Construct both the chair and its flipped conformer for the two stereoisomers below
  2. Determine which stereoisomer will have the faster rate of reaction:           a)         or         b)
  3. Explain this observation mechanistically using full sentences making sure to answer the question of WHY one will undergo an E2 reaction faster than the other.