Correlation of the rates of solvolysis of 2-phenyl-2-ketoethyl bromide and tosylate.
[reaction: see text] The extended Grunwald-Winstein equation has been applied to the specific rates of solvolysis of 2-phenyl-2-ketoethyl bromide and tosylate and the correlation parameters are consistent with an S(N)2 mechanism over the full range of solvents. The k(OTs)/k(Br) ratios are close to unity, consistent with this assignment. Comparisons with the specific rates of solvolysis of 2-phenylethyl bromide and methyl tosylate show only a modest influence upon introduction of the carbonyl group.
Kevill
Dennis N
DN
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA. dkevill@niu.edu
Kim
Chang-Bae
CB