Experiment 10. Nucleophilic Substitution Reactions of Alkyl Halides, 257
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Nucleophilic Substitution Reactions Solvolysis of secondary versus tertiary halides, effects of leaving groups, solvolysis of/and reactions of sodium iodide and silver nitrate with isomers of bromobutane, SN1 and SN2 mechanisms, and hydrolysis of tert-butyl chloride are demonstrated.
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-FluoroacetophenoneNicola Pohl and Kimberly Schwarz Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design. Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ.2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
A Discovery-Based Experiment Involving Rearrangement in the Conversion of Alcohols to Alkyl HalidesRichard A. Kjonaas and Ryand J. F. Tucker This article reports a discovery-based experiment in which students convert three alcohols to alkyl halides under acidic conditions and record the 13C NMR spectrum in each case. By comparing the number of resonances observed with the number of resonances predicted for each possible product, students draw several conclusions about the resulting rearrangement. Kjonaas, Richard A.; Tucker, Ryand J. F. J. Chem. Educ.2008, 85, 100.
Alcohols |
Carbocations |
Gas Chromatography |
NMR Spectroscopy |
Nucleophilic Substitution
The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous ConductivityR. David Pace and Yagya Regmi Presents a quantitative kinetics laboratory exercise featuring the Finkelstein reaction (SN2) for use in the first-semester organic chemistry course that utilizes nonaqueous conductivity as the method by which relevant structuretemperaturesolvent effects are examined. Pace, R. David; Regmi, Yagya. J. Chem. Educ.2006, 83, 1344.
