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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.
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
Semiempirical and DFT Investigations of the Dissociation of Alkyl HalidesJack R. Waas Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the HartreeFock method, and two DFT methods. All five methods agreed generally with the expected empirically known trends in the dissociation of alkyl halides. Waas, Jack R. J. Chem. Educ.2006, 83, 1017.
Alkanes / Cycloalkanes |
Computational Chemistry |
Mechanisms of Reactions |
Molecular Modeling |
Reactions |
Reactive Intermediates |
Thermodynamics |
Elimination Reactions |
Nucleophilic Substitution
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.
