Kinetics of solvolysis of substituted ω-bromo-2-acetonaphthones in aqueous ethanol
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 15,p. 1893-1895
- https://doi.org/10.1039/p29760001893
Abstract
The kinetics of the solvolysis of ω-bromo-2-acetonaphthone in 70, 80, and 90% ethanol have been measured at several temperatures. The Grunwald–Winstein m value is 0.155 ±0.005 over the temperature range of 55–80°. The Hammett equation applies very well to the solvolysis of 6-substituted ω-bromo-2-acetonaphthones and the ρ value in 80% ethanol is 0.33 at 80°. The first-order rate constants are increased by electron-withdrawing groups and decreased by electron-donating groups. The products indicate that there is no rearrangement involving carbonyl oxygen and naphthyl group in the transition state. The reaction may be a simple nucleophilic displacement of bromide by solvent molecules.Keywords
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