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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st330

The compound shown is 2-bromo-1-chloropropane (no configuration specified). Which statements about the isomers of its molecular formula are correct?

  1. AThere are five constitutional isomers
  2. BExactly three of the constitutional isomers are chiral
  3. CCounting enantiomers separately, there are eight isomers in total
  4. D1-Bromo-3-chloropropane is chiral

Answer: A, B, C

Constitutional isomers: 1-bromo-1-chloropropane, 2-bromo-1-chloropropane, 1-bromo-2-chloropropane, 1-bromo-3-chloropropane and 2-bromo-2-chloropropane: 5. A carbon is a stereocentre only if it carries four different groups. 1-Bromo-1-chloropropane (C1: H, Br, Cl, ), 2-bromo-1-chloropropane (C2: H, Br, , ) and 1-bromo-2-chloropropane (C2: H, Cl, , ) are chiral. 1-Bromo-3-chloropropane and 2-bromo-2-chloropropane have no stereocentre. Total = 5 + 3 = 8.
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