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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 principle of minimum bending of orbitalsStewart, George H.; Eyring, Henry The authors present a theory of valency that accounts for a variety of organic and inorganic structures in a clear and easily understood manner. Stewart, George H.; Eyring, Henry J. Chem. Educ.1958, 35, 550.
