Although acetophenone is a methyl ketone, as it is aromatic, it is immiscible in H2O so the last step in the haloform reaction should not occur?
I couldn't find any source regarding the haloform reaction of acetophenone.
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$\begingroup$ Who said it will not give: google.co.in/… $\endgroup$– Nilay GhoshCommented May 8, 2019 at 4:19
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$\begingroup$ No creditable research paper shows. My teacher told that it doesn't show. $\endgroup$– user600016Commented May 8, 2019 at 4:24
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1$\begingroup$ Your teacher may be wrong.check webassign.net/sample/ncsumeorgchem2/lab_4/manual.html which is a lab experiment desinged for the same acetophenone. $\endgroup$– Chakravarthy KalyanCommented May 8, 2019 at 5:19
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$\begingroup$ A phase transfer catalyst can be used in last step $\endgroup$– user66257Commented May 10, 2019 at 8:49
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1 Answer
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Fuson and Bull [Chem. Rev., 15, 275 (1934)] found acetophenone to give a positive iodoform test. They modified the usual procedure, adding dioxane as a cosolvent to better dissolve water-insoluble compounds, since the purely-aqueous method is "uncertain and likely to be misleading" for water-insoluble compounds.
Also cited by those authors as proof of positive haloform test for acetophenone are the following: Lieben, Ann. Spl. Bd., 7, 218 (1870); Kramer, Ber., *13, 1000 (1880); and Cuculescu, Bul. Fac. Stiinte Cernauti, 2, 137 (1928).
