Among the numerous examples of SN1 reactions that occur with incomplete racemization is one reported by Winstein
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Among the numerous examples of SN1 reactions that occur with incomplete racemization is one reported by Winstein in 1952? The optically pure tosylate of 2, 2-dimethy-1-phenyl-1-propanol ([?] D = ? 30.3o) was heated in acetic acid to yield the corresponding acetate ([?] D = + 5.3o). If complete inversion had occurred, the optically pure acetate would have had [?] D = ? 53.6o. What percentage racemization and what percentage inversion occurred in this reaction?
Transcribed Image Text:
H CICH3)3 н СICH3)з OTOS сHзCон TosOH "CHз Observed [alp = +5.3 (optically pure [alp = +53.6) lalp =-30.3 %3D
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