Chemistry - Identification of the organic compound

Solution 1:

The given answer is wrong in many ways:

• 4 did not satisfy both criteria C and E, because it is not a chiral compound to begin with.
• 10 did not satisfy the criteria D, because it does give a precipitate with iodine in presence of $$\ce{NaOH}$$.

That gives only 5 in given answer to satisfy all criteria. Let's eliminate given compounds in systematic order:

That leaves only 5 and 6 to satisfy all criteria.

Solution 2:

I think that correct answer should be 5 and 6 only, because:

• 12 will produce terephthalic acid, instead of benzoic acid as it possess two benzylic-H (also given by 7).

• 4 and 10 doesn't satisfy statement C and D, as you've mentioned.