Keto-enol tautomerism 8-Ketoester

For acetone and the majority of cases in which this keto-enol tautomerism is possible, the keto form is far more stable and little if any enol can be detected. However, with j8-diketones and j8-ketoesters, such factors as intramolecular hydrogen bonding and conjugation increase the stability of the enol form and the equilibrium can be shifted significantly to the right. 

Chloro-2-nitropropane, behaving as an acetone equivalent, reacts by a radical chain process with /3-diketones and 8-ketoesters to give their iso-propylidene derivatives, as keto-enol tautomeric mixtures in some cases, e.g,... 

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