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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.
Experimental Design and Optimization: Application to a Grignard ReactionNaoual Bouzidi and Christel Gozzi This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods. Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ.2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
Synthesis
A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and AcetanilidesEdward M. Treadwell and Tung-Yin Lin An experiment is described involving the nitration of ortho or meta, monosubstituted benzoic acids and monochlorinated acetanilides with nitric acid to evaluate the regioselectivity of addition through computational methods and 1H NMR spectroscopy. Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ.2008, 85, 1541.
Aromatic Compounds |
Computational Chemistry |
Electrophilic Substitution |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry LaboratoryEric Eby and S. Todd Deal This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy. Eby, Eric; Deal, S. Todd. J. Chem. Educ.2008, 85, 1426.
