Prev. Article Next Article Table of Contents

Article

The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment

Supporting Info

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

S. D. Mulder , B. E. Hoogenboom and A. G. Splittgerber

Department of Chemistry, Gustavus Adolphus College, Saint Peter, MN 56082-1498

J. Chem. Educ., 2002, 79 (2), p 218

DOI: 10.1021/ed079p218

Publication Date (Web): February 1, 2002

Section:

History, Education, and Documentation

Abstract

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.