The chlorination of isobutyrophenone: determination of its pKa value and of the course of the reaction
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Chlorination of isobutyrophenone in alkaline aqueous solution leads to formation of α-hydroxyisobutyrophenone as the first detectable intermediate; a slow subsequent oxidation gives benzoate. From the rates of the initial chlorinations we have been able to determine the pKa value for the ketone as 18.18 ± 0.50. α-Chloroisobutyrophenone undergoes surprisingly rapid alkaline hydrolysis, kOH = 71.9 ± 1.5 M−1 s−1. Keywords: isobutyrophenone, chlorination, enolization, pKa, hydrolysis.
2012 ◽
Vol 15
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pp. 54-66
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2004 ◽
Vol 108
(30)
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pp. 6407-6413
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1995 ◽
Vol 142
(8)
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pp. 2695-2698
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2013 ◽
Vol 36
(7)
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pp. 1298-1303
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2020 ◽
Vol 23
(4)
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pp. 233-239
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