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Dolbier HW Solutions 602 - 696 PHENOLS Indeed dione B...

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Indeed, dione B satis fi es the spectroscopic criteria. Carbonyl bands are seen in the infrared spec- trum, and compound B has two sets of protons to be seen in its 1 H NMR spectrum. The two vinyl protons are equivalent and appear at low fi eld, 6.7 ppm; the 4 methylene protons are equivalent to each other and are seen at 2.9 ppm. Compound B is the doubly ketonic tautomeric form of hydroquinone, compound C, to which it isomerizes on standing in water. 24.29 A reasonable fi rst step is protonation of the hydroxyl oxygen. The weak oxygen oxygen bond can now be cleaved, with loss of water as the leaving group. This intermediate bears a positively charged oxygen with only six electrons in its valence shell. Like
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