"P" is an optically active compound with molecular formula C6H12O. When "P" is treated with 2,4-dinitrophenylhydrazine, it gives a positive test. However, in presence of Tollens' reagent, "P" gives a negative test. Predict the structure of "P".
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Answer
(2) [figure]
Solution
Positive 2,4-DNP test P is an aldehyde or a ketone.
Negative Tollens' test P is not an aldehyde P is a ketone. This rules out option (1) (an aldehyde).
Optically active P has a chiral carbon.
Option (2): 3-methylpentan-2-one, C6H12O; C-3 carries H, CH3, C2H5 and COCH3 — four different groups chiral.
Option (3): hexan-2-one — no chiral carbon.
Option (4): 4-methylpentan-2-one — C-4 carries two CH3 groups, not chiral.
P is 3-methylpentan-2-one.
Answer: (2)