Abstract
Abstract Competitive solvolysis has been conducted in binary solvents of water and ethanol on optically active α-phenylethyl chloride at 40.0°C. The extents of inversion (α%) for solvolysis products, i. e., α-phenylethyl alcohol and α-phenylethyl ethyl ether, have been calculated from the optical rotations of these products isolated after ten half-lives, and the values of α% have been plotted Vs. the volume percentage of water. In the region of 90% aqueous ethanol, the two α% lines for the alcohol and the ether intersect with each other. This intersection of the two lines conflicts with any single mechanism for the borderline SN reactions, whereas the dual mechanism can explain this phenomenon without any difficulty. In the region of a 100% water-solvent (a typical medium for the SN1 solvolysis), the two lines do not converge to the same α% value. On the basis of these findings, a general mechanism of racemization for the SN1 solvolysis has also been discussed.
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