Examination of a Reaction Mechanism by Polarimetry: An Experiment for the Undergraduate Organic Chemistry Laboratory

An undergraduate Organic chemistry laboratory experiment involving the use of polarimetry to determine a reaction mechanism is described. The experiment has been shown to be successful with chiral mandelic acid and POCl3 and with chiral lactic acid and HBr. The substitution mechanisms of these react...

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Veröffentlicht in:Journal of chemical education 1996-06, Vol.73 (6), p.567
Hauptverfasser: Kelly, Chad O, Mosher, Melvyn W, Mosher, Michael D
Format: Artikel
Sprache:eng
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Zusammenfassung:An undergraduate Organic chemistry laboratory experiment involving the use of polarimetry to determine a reaction mechanism is described. The experiment has been shown to be successful with chiral mandelic acid and POCl3 and with chiral lactic acid and HBr. The substitution mechanisms of these reactions proceed with 1% and 38% SN2 character respectively.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed073p567