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Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic LaboratoryJohn J. Nash, Marnie A. Leininger, and Kurt Keyes An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism. Nash, John J.; Leininger, Marnie A.; Keyes, Kurt. J. Chem. Educ.2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry StudentsJennifer N. Shepherd and Jason R. Stenzel Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all. Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ.2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
The Substitution–Elimination Mechanistic Disc MethodPaul T. Buonora and Yu Jin Lim In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented. Buonora, Paul T.; Lim, Yu Jin. J. Chem. Educ.2004, 81, 368.