Concept explainers
Phenols generally are not changed on treatment with sodium borohydride followed by acidification to destroy the excess, unreacted hydride. For example, the 1,2-, 1,3-, and 1,4-benzenediols and 1,2,3-benzenetriol are unchanged under these conditions. However, 1,3,5-benzenetriol (phloroglucinol) gives a high yield of a product A that has these properties:
MS
IR
(a) What is the structure of A?
(b) Suggest a mechanism by which the above reaction occurred. (1,3,5-Benzenetriol is known to have more tendency to exist in a ketotautomeric form than do simpler phenols.)
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