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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm045

A cyclopentane ring carries a methyl group and a 2-methylpropyl group on carbons that are in a 1,3 relationship. What is the IUPAC name of the compound?

  1. A1-methyl-3-(1-methylpropyl)cyclopentane
  2. B1-methyl-3-(2-methylpropyl)cyclopentane
  3. C3-methyl-1-(2-methylpropyl)cyclopentane
  4. D1-(2-methylpropyl)-3-methylcyclopentane

Answer: B

Both ways of numbering give the locant set {1,3}. The tie is broken by giving locant 1 to the substituent cited first in alphabetical order. 'Methyl' precedes 'methylpropyl' (the shorter name comes first when the letters are otherwise identical), so methyl gets C1. The prefixes are written alphabetically: 1-methyl-3-(2-methylpropyl)cyclopentane.
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