Does resorcinol give positive iodoform test?

Question

It's given in my book that other than the usual compounds that answer iodoform test, resorcinol (benzene-1,3-diol) also gives positive iodoform test. Is this because of tautomerization which gives a diketone with an active methylene group? But why should a ring lose its aromaticity by doing so?

Answer 1

It would be reacting through electrophilic aromatic substitution. In base, phenols are pretty strong nucleophiles. Even with no catalyst phenol reacts with most/all halogens. I don't think traditional CHI₃ (Iodoform) product would be forming. But the iodine you add would get used up, changing the color/appearance of the solution.

In the product, hydrogens on the ring ortho/para to the hydroxyl groups would be replaced with iodines.