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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st326

The compound shown is 1-chloro-2-methylcyclopropane (no configuration specified). Consider only the cyclic (ring-containing) isomers of its molecular formula , with rings treated as planar. Which statements are correct?

  1. AThere are four cyclic constitutional isomers
  2. B1-Chloro-2-methylcyclopropane has four stereoisomers
  3. CThe total number of cyclic isomers including all stereoisomers is seven
  4. DChlorocyclobutane is chiral

Answer: A, B, C

Cyclic constitutional isomers of : chlorocyclobutane, 1-chloro-1-methylcyclopropane, 1-chloro-2-methylcyclopropane and (chloromethyl)cyclopropane: 4. Only 1-chloro-2-methylcyclopropane has stereocentres; its two centres carry different groups (Cl versus ), so both cis and trans are chiral and there are stereoisomers with no meso form. Chlorocyclobutane has a mirror plane through C1 and C3 and is achiral. Total cyclic isomers = 1 + 1 + 4 + 1 = 7.
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