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Computational Investigations for Undergraduate Organic Chemistry: Modeling Markovnikov and anti-Markovnikov Reactions for the Formation of Alkyl Halides and Alcohols
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Abstract
Early in sophomore-level organic chemistry students are introduced to reaction mechanisms, and it is at this stage when they tend to become convinced that memorization is the skill they need to hone in order to succeed. This paper describes how the early introduction of molecular modeling for the study of reaction mechanisms leading to alcohols from alkenes can increase students' involvement in their own learning and can effectively challenge their misapprehension about memorization. It describes the use of modeling to emphasize structure-reactivity relationships rather than focusing on reagents, and tries to show that the use of molecular modeling is well suited for classroom and laboratory use as well as to assist students' study. Particularly in an educational setting that stresses collaborative or interactive learning, the methodology described here can be rewarding for teachers and students alike.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Feature):
Teaching with TechnologyKeywords (Pedagogy):
Computer-Based LearningKeywords (Subject):
Computational ChemistryCiting Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?
Predrag-Peter Ilich , Lucas S. Rickertsen and Erienne BeckerJournal of Chemical Education2006 83 (11), 1681Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?
Predrag-Peter Ilich , Lucas S. Rickertsen and Erienne BeckerJournal of Chemical Education2006 83 (11), 1681For 137 years Markovnikov's rule has been extensively used in organic chemical education and research to describe the regioselectivity in electrophilic addition reactions to alkenes and alkynes. When the structures of the final reaction products are used ...
Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides
Jack R. WaasJournal of Chemical Education2006 83 (7), 1017Semiempirical and DFT Investigations of the Dissociation of Alkyl Halides
Jack R. WaasJournal of Chemical Education2006 83 (7), 1017Enthalpy changes corresponding to the gas phase heats of dissociation of 12 organic halides were calculated using two semiempirical methods, the Hartree–Fock method, and two DFT methods. These calculated values were compared to experimental values where ...
Exploring Organic Mechanistic Puzzles with Molecular Modeling
Gail Horowitz and Gary SchwartzJournal of Chemical Education2004 81 (8), 1136Exploring Organic Mechanistic Puzzles with Molecular Modeling
Gail Horowitz and Gary SchwartzJournal of Chemical Education2004 81 (8), 1136Molecular modeling projects in the form of mechanistic organic puzzles are described. Students, working in small groups, deduced reaction mechanisms and calculated heats of formation of intermediates and products in order to predict thermodynamic and ...
Entropy Explained: The Origin of Some Simple Trends
Lori Watson , Odile EisensteinJournal of Chemical Education2002 79 (10), 1269Entropy Explained: The Origin of Some Simple Trends
Lori Watson , Odile EisensteinJournal of Chemical Education2002 79 (10), 1269Density functional theory computational methods were used to calculate the entropies of various molecules; computed entropies correlated closely with measured values. For organic systems, an average of 8.4 kcal/mol for the reaction entropy (one particle ...
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- Received: August 03, 2009
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