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ERIC Number: EJ826612
Record Type: Journal
Publication Date: 2008-Apr
Pages: 3
Abstractor: As Provided
Reference Count: 13
ISSN: ISSN-0021-9584
Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters
Keenan, Sheue L.; Peterson, Karl P.; Peterson, Kelly; Jacobson, Kyle
Journal of Chemical Education, v85 n4 p558-560 Apr 2008
Seven p-nitrophenyl benzoate esters (p-nitrophenyl benzoate, p-nitrophenyl m-anisate, p-nitrophenyl p-anisate, p-nitrophenyl m-chlorobenzoate, p-nitrophenyl p-chlorobenzoate, p-nitrophenyl m-toluate, p-nitrophenyl p-toluate) were synthesized and characterized by students in a second-semester organic laboratory course. In a subsequent laboratory period, the rate constants for the base hydrolysis of these esters were measured by monitoring the formation of the p-nitrophenoxide ion by UV-vis spectrophotometry. The Hammett equation rho constant for this hydrolysis reaction was then determined. The two-experiment sequence was developed to demonstrate structure-reactivity relationships and pseudo-first-order reaction kinetics. The students gained experience in organic synthesis and characterization, performing kinetics studies by spectrophotometry, and carrying out data analysis using spreadsheet software. (Contains 3 schemes, 1 table, and 3 figures.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A