Lithium aluminum hydride reduction of 1,2-epoxy-2-methylpropane gives, as expected, predominantly tert-butyl alcohol.
When the reduction is carried out with an LiAlH4/AlCl3 mixture, however, epoxide rearrangement precedes reduction and isobutyl alcohol becomes the major product. This rearrangement was confirmed by a deuterium-labeling experiment in which an LiAlD4/AlCl3 mixture was used. Where was the deuterium located in the isobutyl alcohol product?
A.
B.
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