JEE MainChemistryAldehydes and Ketones
An optically active compound "P" with molecular formula C₆H₁₂O gives a positive 2,4-DNP test and a positive iodoform test, but a negative Tollens test. When "P" is treated with I₂/NaOH followed by acidification, it yields a carboxylic acid "Q". The IUPAC name of compound "Q" is:
Options
- A3-methylpentanoic acid
- B3-methylbutanoic acid
- C2-methylbutanoic acid
- D2,2-dimethylpropanoic acid
Correct answer
C. 2-methylbutanoic acid
Step-by-step solution
Compound P gives a positive 2,4-DNP test, indicating it is a carbonyl compound. A negative Tollens test indicates P is a ketone, not an aldehyde. A positive iodoform test indicates P is a methyl ketone (contains a CH₃-CO- group). The molecular formula is C₆H₁₂O . The possible methyl ketones are hexan-2-one, 3-methylpentan-2-one, 4-methylpentan-2-one, and 3,3-dimethylbutan-2-one. Since P is optically active, it must have a chiral center. Only 3-methylpentan-2-one ( CH₃-CO-CH(CH₃)-CH₂-CH₃ ) is chiral. When 3-methylpe