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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx274

The alkane shown undergoes free-radical monochlorination. Counting enantiomers as separate compounds where relevant, select all correct statements.

  1. AFour constitutional monochlorides are possible.
  2. BEight monochlorination products are possible when enantiomers are counted separately.
  3. CThree of the constitutional monochlorides are chiral.
  4. DThe product formed by substitution at the tertiary C-H is achiral.

Answer: A, B, D

3-Methylpentane has four sets of equivalent hydrogens (the two ethyl CH3, the two CH2, the tertiary CH, and the methyl on C-3), so four constitutional monochlorides arise. Of these only 1-chloro-3-methylpentane (one stereocentre) and 2-chloro-3-methylpentane (two stereocentres) are chiral, giving 2 + 4 + 1 + 1 = 8 stereoisomers. Three chiral constitutional isomers is wrong (two), and the tertiary-hydrogen product, 3-chloro-3-methylpentane, is achiral. RDKit confirms 4 and 8.
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