Suppose we have some optically pure (R)-2-butyl acetate that has been labeled with the heavy 18O isotope

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Suppose we have some optically pure (R)-2-butyl acetate that has been "labeled" with the heavy 18O isotope at one oxygen atom as shown.
Suppose we have some optically pure (R)-2-butyl acetate that has

(a) Draw a mechanism for the hydrolysis of this compound under basic conditions. Predict which of the products will contain the 18O label. Also predict whether the butan-2-ol product will be pure (R), pure (S), or racemized.
(b) Repeat part (a) for the acid-catalyzed hydrolysis of this compound.
(c) Explain how you would prove experimentally where the 18O label appears in the products. (18O is not radioactive.)

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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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