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Electrophilic Substitution in Naphthalene: Kinetic vs Thermodynamic Control

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Leslie D. Field , Sever Sternhell and Howard V. Wilton

The University of Sydney, Division of Organic Chemistry, Sydney, N.S.W. 2006, AUSTRALIA

J. Chem. Educ., 1999, 76 (9), p 1246

DOI: 10.1021/ed076p1246

Publication Date (Web): September 1, 1999

Section:

History, Education, and Documentation

Abstract

Deuterium-protium exchange in naphthalene effected by trifluoroacetic acid and aluminium tris-trifluoroacetate was followed by proton NMR spectroscopy. Initially, the partly deuterated naphthalene has a ratio of protium to deuterium at the C-1 (a) position smaller than unity, reflecting a higher reactivity towards electrophiles at this position. However, after equilibrium has been established, this ratio becomes unity within the experimental accuracy of the measurement, reflecting the lack of any thermodynamic effect. These results are a potential "textbook" example of kinetic versus thermodynamic control, which is much clearer than the usually quoted reversible sulfonation of naphthalene.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Subject):

Kinetics

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