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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap070

Compound X, $C X_{4} H X_{10} O$ , is optically active and gives a yellow precipitate with $I X_{2}$ / $NaOH$ . It gives turbidity with $ZnCl X_{2}$ /conc. $HCl$ only after about five minutes at room temperature, and on oxidation with $CrO X_{3}$ it gives a product that forms an orange precipitate with 2,4-dinitrophenylhydrazine but does not reduce Tollens reagent. X is

Abutan-1-ol
Bethoxyethane
C2-methylpropan-2-ol
Dbutan-2-ol

Answer: D

The slow turbidity in about 5 minutes indicates a secondary alcohol. Among

C X_{4} H X_{10} O

alcohols only butan-2-ol is both secondary and chiral, and it contains

CH X_{3} CH (OH) X^{-}

for the iodoform test. Its oxidation product, butanone, is a ketone: it reacts with 2,4-DNP and does not reduce Tollens reagent.

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