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A Safer, Discovery-Based Nucleophilic Substitution Experiment
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Abstract
A discovery-based nucleophilic substitution experiment is described in which students compare the reactivity of chloride and iodide ions in an SN2 reaction. This experiment improves upon the well-known "Competing Nucleophiles" experiment in that it does not involve the generation of hydrogen halide gas. The experiment also introduces students to the subject of phase-transfer catalysis.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
CatalysisCiting Articles
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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

The Study of Substitution and Elimination Reactions Using Gas Chromatography: An Examination of the Effects of Alkane and Base Structure on Product Distributions
Donald L. WharryJournal of Chemical Education2011 88 (12), 1720-1723The Study of Substitution and Elimination Reactions Using Gas Chromatography: An Examination of the Effects of Alkane and Base Structure on Product Distributions
Donald L. WharryJournal of Chemical Education2011 88 (12), 1720-1723An experiment that compares product distribution obtained by either substitution or elimination utilizing alkyl bromides and methoxide, ethoxide, or t-butoxide as the base (or nucleophile) is described. The change in product distribution caused by steric ...

Probing the Reactivity of Dimethylsulfoxonium Methylide with Conjugated and Nonconjugated Carbonyl Compounds: An Undergraduate Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
James A. Ciaccio, Elena L. Guevara, Rabeka Alam and Christina D. D’agrosaJournal of Chemical Education2010 87 (8), 850-853Probing the Reactivity of Dimethylsulfoxonium Methylide with Conjugated and Nonconjugated Carbonyl Compounds: An Undergraduate Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
James A. Ciaccio, Elena L. Guevara, Rabeka Alam and Christina D. D’agrosaJournal of Chemical Education2010 87 (8), 850-853We introduce students to dimethylsulfoxonium methylide (DMSY) epoxidation of aryl and nonconjugated aliphatic aldehydes and ketones without revealing that DMSY cyclopropanates enones by Michael-initiated ring closure (MIRC). Each student performs the ...
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History
- Received: August 03, 2009
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