Lithium aluminum hydride reduction of 1,2-epoxy-2-methylpropane gives, as expected
Chapter 16, Problem 16.46(choose chapter or problem)
Lithium aluminum hydride reduction of 1,2-epoxy-2-methylpropane gives, as expected, predominantly tert-butyl alcohol. H3C H H3C H O 1,2-Epoxy-2-methylpropane tert-Butyl alcohol (97%) Isobutyl alcohol (3%) 1. LiAlH4 2. H3O OH H3C C CH3 CH3 H H3C C CH2OH CH3 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. D H3C C CH2OH CH3 H H3C C CHDOH CH3
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