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Which statement is correct for the following four molecules ?

Four 4H-thiochromene S-oxides: I 4,4-dichloro-2,3-dimethyl; II and IV both 2-methyl-3-chloro with chlorine and methyl on C4, drawn with opposite wedges at C4; III 2,3-dichloro-4,4-dimethyl

  • A.I and II are chiral
  • B.II and IV are chiral
  • C.I, II, III and IV are chiral
  • D.I and IV are chiral

Answer: C

The correct statement is I, II, III and IV are chiral.

All four molecules are sulfoxides. A sulfoxide sulfur carries an oxygen, two different carbon groups (here the aromatic ring carbon and the vinylic C2) and a lone pair, in a pyramidal arrangement that does not invert at room temperature. So each sulfur is a stereogenic centre, and none of the molecules has a mirror plane through it.

That is why even I and III are chiral, although C4 in each carries two identical groups (two Cl in I, two CH3 in III) and is not a stereocentre. II and IV have a stereogenic C4 as well as the sulfur. The options listing only some of the molecules overlook the sulfoxide stereocentre.

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