Identification of the organic compound An organic compound A $(\ce{C10H14O})$ exhibits following characteristics.
A) It reacts with metallic sodium to give a colorless odorless gas.
B) It is oxidized by $\ce{KMnO4}$ to benzoic acid.
C) It can be resolved.
D) It does not give precipitate with iodine in presence of $\ce{NaOH}.$
E) It changes the color of acidified potassium dichromate from orange to bluish
green, and gives a chiral compound.
How many of the following compounds satisfy all the five criteria from A to E?


The given answer is the compounds 4, 5, 10 satisfy the criteria but I think the compounds 5, 6, 12 satisfy the criteria.
From statement A, we come to know it's an alcohol (which is common to every compound).
From statement B, we come to know that it has a benzylic hydrogen (which rules out the compound 11).
From statement C, we come to know that it has a chiral carbon. (which rules out options 4, 7, 9).
From statement D, we come to know that $\ce{OH}$ group is not attached to a methyl group (which rules out options 3, 10).
For statement E, I guess potassium dichromate will oxidise 2° alcohol to ketone and 1° alcohol to carboxylic acid and the compound still remains chiral (which rules out options 1, 2, 8).
So where's the mistake?
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.