Dolbier HW Solutions 354

Dolbier HW Solutions 354 - 448 ALDEHYDES AND KETONES...

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17.27 Wolff Kishner reduction converts a carbonyl group (C ? O) to a methylene group (CH 2 ). 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. 17.28 Hydration of formaldehyde by H 2 17 O produces a gem -diol in which the labeled and unlabeled hydroxyl groups are equivalent. When this gem -diol reverts to formaldehyde, loss of either of the hydroxyl groups is equally likely and leads to eventual replacement of the mass-16 isotope of oxygen by 17 O. This reaction has been monitored by 17 O NMR spectroscopy; 17 O gives an NMR signal, but 16 O does not. 17.29 First write out the chemical equation for the reaction that takes place. Vicinal diols (1,2-diols) react
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