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2005•The Journal of Organic ChemistryRequires access

Correlation of the Rates of Solvolysis of 2-Phenyl-2-ketoethyl Bromide and Tosylate

Dennis N. Kevill, Chang-Bae Kim

Open publisher page 15 citations

Abstract

[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.

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[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.

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Available abstract

[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.

Key concepts: Solvolysis, Bromide, Chemistry, Medicinal chemistry, Organic chemistry, Hydrolysis

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Correlation of the Rates of Solvolysis of 2-Phenyl-2-ketoethyl Bromide and Tosylate — Research Paper | ScholarLens