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JEE Advanced levelSingle correct optionDifficulty 3 of 3nm201

Methylcyclopropane is dichlorinated on the ring or the side chain. How many dichloro structural isomers of are possible (stereoisomers not counted)?

  1. A6
  2. B4
  3. C5
  4. D7

Answer: A

Side chain only: 1,1 on the methyl (dichloromethylcyclopropane) ; one Cl on the side chain and one on the ring at C1 (1-(chloromethyl)-1-chlorocyclopropane), at C2 (1-chloro-2-(chloromethyl)cyclopropane). Ring only: 1,1-dichloro-2-methyl ; 1,2-dichloro-1-methyl (Cl on the methyl-bearing carbon and a neighbour) ; 1,2-dichloro-3-methyl. Total 6. Verified by substituting every H pair by Cl and de-duplicating.
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