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Discovery-Based S[subscript N]Ar Experiment in Water Using Micellar Catalysis

Title: Discovery-Based S[subscript N]Ar Experiment in Water Using Micellar Catalysis
Language: English
Authors: Landstrom, Evan B. (ORCID 0000-0002-5789-6106); Nichol, Meghan; Lipshutz, Bruce H. (ORCID 0000-0001-9116-7049); Gainer, Morgan J. (ORCID 0000-0002-4034-687X)
Source: Journal of Chemical Education. Nov 2019 96(11):2668-2671.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 4
Publication Date: 2019
Document Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Descriptors: Discovery Learning; Science Experiments; Water; Organic Chemistry; Science Laboratories; Laboratory Experiments; College Students; Science Instruction; College Science; Systems Approach; Chemistry; Spectroscopy
DOI: 10.1021/acs.jchemed.9b00310
ISSN: 0021-9584
Abstract: Micellar catalysis has become an important aspect of the chemical industry's effort to "go green". However, this chemistry has yet to be fully explored in educational settings such as second-year organic chemistry laboratories. Reported herein is a discovery-based nucleophilic aromatic substitution experiment that introduces chemistry students to micellar catalysis, green chemistry, and systems thinking. The students prepare tandem reactions in water to explore how the leaving group identity affects the rate of reaction and how the reaction incorporates principles of green chemistry. The product of the fastest reaction is isolated through recrystallization, and the product's identity is verified through infrared spectroscopy and melting point analysis.
Abstractor: As Provided
Entry Date: 2019
Accession Number: EJ1234592
Database: ERIC