Resumen de The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment
S. D. Mulder, Bernard E. Hoogenboom, Allan G. Splittgerber
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.
