Ch. 7 - Substitution 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

Solution: Complete the following mechanism for an SN1 reaction that occurs when 2-chloro-2-methylbutane is heated in water. NOTE, ALTHOUGH AN E1 PROCESS WILL ACCOMPANY THIS SN1 REACTION, WE ARE ONLY INTERESTED IN THE SN1 MECHANISM FOR THIS PROBLEM. Use appropriate arrows to show all movement of electrons, show all non-bonding electrons as dots and show any formal charges. If any of the species are really racemic mixtures of enantiomers, you only need to draw one stereoisomer and write "racemic". In the boxes provided, write which kind of mechanisitc element is being shown for that step, i.e. "make a bond", etc.

Problem

Complete the following mechanism for an SN1 reaction that occurs when 2-chloro-2-methylbutane is heated in water. NOTE, ALTHOUGH AN E1 PROCESS WILL ACCOMPANY THIS SN1 REACTION, WE ARE ONLY INTERESTED IN THE SN1 MECHANISM FOR THIS PROBLEM. Use appropriate arrows to show all movement of electrons, show all non-bonding electrons as dots and show any formal charges. If any of the species are really racemic mixtures of enantiomers, you only need to draw one stereoisomer and write "racemic". In the boxes provided, write which kind of mechanisitc element is being shown for that step, i.e. "make a bond", etc.