Suppose we have some optically pure (R)-2-butyl acetate that has been labeled with the
Chapter 21, Problem PROBLEM 21-16(choose chapter or problem)
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. CH3 C O C O CH2CH3 CH3 H 18 (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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