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2002
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In the Laboratory
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The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment
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S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber
Department of Chemistry, Gustavus Adolphus College, Saint Peter, MN 56082-1498
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February 2002
Vol. 79 No. 2
p. 218
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| Abstract |
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This paper describes the preparation, characterization, and hydrolysis reactions in aqueous basic medium of three nitro derivatives of a simple sulfonate ester, phenyl phenylmethanesulfonate, C6H5-CH2-SO2-O-C6H5. The three nitro esters are p-nitrophenyl phenylmethanesulfonate, C6H5-CH2-SO2-O-C6H4-NO2-p, ester 1; phenyl p-nitrophenylmethanesulfonate, p-O2N-C6H4-CH2-SO2-O-C6H5 ester 2; and p-nitrophenyl p-nitrophenylmethanesulfonate, p- O2N-C6H4-CH2-SO2-O-C6H4-NO2-p ester 3. Laboratory experiments involving this system include ester synthesis, purification and characterization, and visual observations and kinetic analysis of hydrolysis reactions of ester 2 using a digital visible spectrophotometer.
Experimental data are interpreted in light of chemical principles already familiar to students, which enables them to construct a plausible mechanism for the hydrolytic process. These principles are all encountered during the first semester organic chemistry course, and the students should therefore be able to see connections between lecture concepts and their laboratory observations.
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| Supplement |
Instructor notes, which contain synthetic procedures, and a student handout, which includes student instructions and a report sheet, are available. The report sheets involve compilations of experimental data, conclusions drawn from the data, and a series of questions to be answered by the student.
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 Contents |
JCE2002p0218W folder containing two Microsoft Word documents
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| More Information |
Citation |
Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002 79 218.
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Keywords |
Laboratory Instruction; Mechanisms; Organic Chemistry
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History |
Created:
Last Updated: |
January 2, 2002
March 16, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
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February
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218
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