The enol content and acidity of cyclopentanone, cyclohexanone, and acetone in aqueous solution
Abstract
From observations of its rapid reaction with bromine, the equilibrium proportions of enol in aqueous solutions of cyclopentanone and cyclohexanone at 25° are 1·3 × 10–5 and 4·1 × 10–6, respectively. In alkaline solutions the same method gives the content of enol plus enolate ion, leading to pK 16·7 for the keto forms of both ketones. Similar measurements with acetone were inconclusive, but suggested a smaller enol content than had previously been assumed, and a pK value between 19 and 20.
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