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ERIC Number: EJ920093
Record Type: Journal
Publication Date: 2010-Sep
Pages: 2
Abstractor: As Provided
Reference Count: 18
ISSN: ISSN-0021-9584
Carbocation Rearrangement in An Electrophilic Aromatic Substitution Discovery Laboratory
Polito, Victoria; Hamann, Christian S.; Rhile, Ian J.
Journal of Chemical Education, v87 n9 p969-970 Sep 2010
In this discovery laboratory, students performed electrophilic aromatic substitution reactions between 1,4-dimethoxybenzene and either 2-methyl-2-butanol or 3-methyl-2-butanol with sulfuric acid as a catalyst. The carbocation from 3-methyl-2-butanol undergoes a hydride shift, and hence, both reactions afford 1,4-bis(1,1-dimethylpropyl)-2,5-dimethoxybenzene in high yields. NMR spectroscopy, infrared spectroscopy, mass spectrometry, and the melting point all indicate identical products from both reactions. Students determine the product identity from the spectroscopy results. Melting point and gas chromatography confirm that the products are identical, promoting discussion of carbocation stability and the hydride shift mechanism. (Contains 2 notes and 1 figure.)
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:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A