The following bicyclic ketone has two a-carbons and three a-hydrogens. When this
Chapter 16, Problem 16.45(choose chapter or problem)
The following bicyclic ketone has two a-carbons and three a-hydrogens. When this moleculeis treated with D2O in the presence of an acid catalyst, only two of the three a-hydrogensexchange with deuterium. The a-hydrogen at the bridgehead does not exchange. How do you account for the fact that two a-hydrogens do exchange but the thirddoes not? You will find it helpful to build models of the enols by which exchange ofa-hydrogens occurs.
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