[Pranav]

This question appeared in my exam but I don't see any possible answers to this.

An organic compound 'A' (C₉H₁₀O) forms orange precipitate. 'B' with 2,4-DNP. 'A' gives yellow precipitate. 'C' with iodine and NaOH along with a colourless compound 'D'. 'A' does not reduce Tollens reagent or Fehling solution nor does it decolourise Br₂ water. On drastic oxidation of 'A' with chromic acid, a carboxylic acid 'E' of C₇H₆O₂ is formed. Identify A to E.

One of the structures I came up with is this:

However, I don't think this would give the haloform reaction.
 

[Hunter2]

It will. All molecules CH₃CHOH-R or CH₃CO-R give this reaction.

[Pranav]

It will. All molecules CH₃CHOH-R or CH₃CO-R give this reaction.

I know they give haloform reaction but the mechanism involves halogenation at the acidic alpha hydrogens. In the structure I have drawn, the acidic hydrogen is present at the carbon directly attached to the ring.

[Hunter2]

What about the C- on the right side?

[Pranav]

What about the C- on the right side?

Yes, it do posses acidic hydrogens but the hydrogens present on the left C- are more acidic. Or have I misunderstood something?

[Hunter2]

The question is how much acidic the H has to be. The best is do the experiment.

[Pranav]

The question is how much acidic the H has to be. The best is do the experiment.

Doing experiment is not possible for me, thanks for the *delete me*

EDIT: Why does the word "help" is replaced with *delete me*?