17.27Wolff–Kishner reduction converts a carbonyl group (C?O) to a methylene group (CH2).Treatment of the alkene with m-chloroperoxybenzoic acid produces an epoxide, compound B.Epoxides undergo reduction with lithium aluminum hydride to form alcohols (Section 16.12).Chromic acid oxidizes the alcohol to a ketone.17.28Hydration of formaldehyde by H217O produces agem-diol in which the labeled and unlabeledhydroxyl groups are equivalent. When thisgem-diol reverts to formaldehyde, loss of either of thehydroxyl groups is equally likely and leads to eventual replacement of the mass-16 isotope ofoxygen by17O.This reaction has been monitored by 17O NMR spectroscopy; 17O gives an NMR signal, but 16O doesnot.17.29First write out the chemical equation for the reaction that takes place. Vicinal diols (1,2-diols) react
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