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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.
Nucleophilic Substitution
Diels-Alder Visualization Several computer animations of a Diels-Alder reaction that were created as an undergraduate student project are presented.
Addition Reactions |
Alkenes
Addition Reactions of Alkenes The Diels-Alder reaction, addition of oxygen to tetrakis(N, N-dimethylamino) ethylene, polymerization of ethylene, and addition of iodine to a-pinene are demonstrated. Molecular models of ethene are shown.
The Iodochlorination of Styrene: An Experiment That Makes a DifferenceR. Gary Amiet and Sylvia Urban This purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR. Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ.2008, 85, 962.
Alkenes |
Constitutional Isomers |
Gas Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis |
Student-Centered Learning
Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. Rettig Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected. Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
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.
