Compound A undergoes hydrolysis of its acetal function in dilute sulfuric acid to yield
Chapter 22, Problem 22.31(choose chapter or problem)
Compound A undergoes hydrolysis of its acetal function in dilute sulfuric acid to yield 1,2-ethanediol and compound B (C6H6O2), mp 54C. Compound B exhibits a carbonyl stretching band in the infrared at 1690 cm1 and has two singlets in its 1 H NMR spectrum, at 2.9 and 6.7, in the ratio 2:1. On standing in water or ethanol, compound B is converted cleanly to an isomeric substance, compound C, mp 172173C. Compound C has no peaksattributable to carbonyl groups in its infrared spectrum. Identify compounds B and C.
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