As far as I know it's not possible for 1,3,5-trihydroxybenzene to give the haloform reaction.

The prerequisites(that I know) for the haloform reaction are:

Only those organic compounds which can be converted to a methyl ketone or acetaldehyde by means of oxidation (by $\ce{NaOX}$ ($\ce{NaOH + X2}$) type agents which are present in the reaction mixture) give this reaction. And obviously a methyl ketone or acetaldehyde would give this reaction too.

So the problem is I don't see how 1,3,5-trihydroxybenzene meet those prerequisites. Is there any way out because in a recent practice test I came to know that 1,3,5-trihydroxybenzene does give the haloform reaction.

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    $\begingroup$ Phloroglucinol(1,3,5 trihydroxybenzene) will not give haloform reaction. See this: chemistry.stackexchange.com/questions/50538/… $\endgroup$ – Nilay Ghosh Apr 30 '18 at 13:15
  • $\begingroup$ Did they give you the reason or even a hint as to why it gives the haloform reaction? $\endgroup$ – Gaurang Tandon Apr 30 '18 at 13:30
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    $\begingroup$ Then that's probably the wrong answer. Although you may surely wish to keep this question open for a while, just in case someone has more detailed views. $\endgroup$ – Gaurang Tandon Apr 30 '18 at 13:56
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    $\begingroup$ There are two things here: 1) undergo actual haloform reaction 2) react, when tested for methyl ketone group, with iodine and sodium hydroxide mixture. First is impossible - no way you'll get haloform, second very probable. $\endgroup$ – Mithoron Apr 30 '18 at 22:35
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    $\begingroup$ Actually it does give iodoform test. Its tautomer which is cyclohex-1,3,5-trione exists in quite a good amount in the solution which is why it gives the rest. $\endgroup$ – FreakyLearner May 4 '18 at 12:10

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