The tetrabutylammonium salt of isotopically chiral phenyl phosphate was heated in the
Chapter 25, Problem 25.31(choose chapter or problem)
The tetrabutylammonium salt of isotopically chiral phenyl phosphate was heated in the polar aprotic solvent acetonitrile containing excess tert-butyl alcohol, and isotopically substituted tert-butyl phosphate was isolated. An analysis of its stereochemistry showed that it was completely racemic. (See Fig. P25.31, p. 1324.) Explain this result with a mechanism. (Hint: Think about the reactive intermediate, and also consider the possible role of the solvent.)
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