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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm054

An alkane of molecular formula gives exactly two different monochloro products (structural isomers only) on free-radical monochlorination. What is its IUPAC name?

  1. A2,2-dimethylbutane
  2. B2-methylpentane
  3. C2,3-dimethylbutane
  4. D3-methylpentane

Answer: C

Count the distinct hydrogen environments of each C6H14 isomer. Hexane has 3, 2-methylpentane has 5, 3-methylpentane has 4 and 2,2-dimethylbutane has 3. 2,3-Dimethylbutane, (CH3)2CH-CH(CH3)2, has only two: the twelve equivalent primary H and the two equivalent tertiary H. So it gives 2 monochloro products.
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