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Counterion Effects in the Nucleophilic Substitution Reaction of the Acetate Ion with Alkyl Bromides in the Synthesis of Esters

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Elizabeth M. Valentín and Ingrid Montes

Department of Chemistry, University of Puerto Rico-Río Piedras Campus, San Juan, Puerto Rico 00931

Waldemar Adam

Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97094 Würzburg, Germany; and Department of Chemistry, University of Puerto Rico-Río Piedras Campus, San Juan, Puerto Rico 00931

J. Chem. Educ., 2009, 86 (11), p 1315

DOI: 10.1021/ed086p1315

Publication Date (Web): November 1, 2009

Abstract

Esters are often employed as artificial flavorings in foods and drinks, since the more volatile ones possess distinctive odors characteristic of common fruits. The present laboratory experiment introduces students to the esterification method in which a nucleophilic substitution reaction (either S_N2 or S_N1) between an alkyl halide and metal carboxylate is employed. The students learn that the metal counterion plays an important role with regard to the efficiency of the reaction and that the ester yield depends on the type of mechanism, namely, whether an S_N2 or S_N1 process occurs. For this purpose, a simple ester is synthesized, its yield determined gravimetrically, its purity established by gas chromatography analysis, and its identity assessed by mass spectrometry. The results are explained in terms of Pearson's hard and soft acid–base principle (HSAB), an empirical concept rarely covered in introductory organic chemistry.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Acids / Bases

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Molecular Models of Esters with Recognizable Odors
William F. Coleman
Journal of Chemical Education2009 86 (11), 1344
- Molecular Models of Esters with Recognizable Odors
  William F. Coleman
  Journal of Chemical Education2009 86 (11), 1344
  This month’s featured molecules include esters having easily recognizable odors: isobutyl formate (raspberry), methyl anthranilate (grapes), ethyl acetate (nail polish remover), methyl salicylate (wintergreen), ethyl propionate (rum), methyl butyrate (...
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