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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm048

A cyclohexane ring carries an ethyl, a methyl and a propyl group on three consecutive ring carbons, with the propyl group on the middle carbon. What is the IUPAC name of the compound?

  1. A1-ethyl-3-methyl-2-propylcyclohexane
  2. B2-ethyl-1-methyl-3-propylcyclohexane
  3. C1-ethyl-2-propyl-3-methylcyclohexane
  4. D3-ethyl-1-methyl-2-propylcyclohexane

Answer: A

Either direction gives the locant set {1,2,3}, so the tie is broken by alphabetical order: ethyl is cited first among ethyl, methyl and propyl and receives the lowest locant, 1. Propyl on the middle carbon is then 2 and methyl is 3. The prefixes are then written in alphabetical order: 1-ethyl-3-methyl-2-propylcyclohexane.
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