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JEE Main levelNumerical answerDifficulty 2 of 3st284

The compound shown is 2,3,4-trichloropentane (no configuration is specified). How many of its stereoisomers are achiral (meso) forms? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 2

C2 and C4 are stereocentres and C3 is pseudoasymmetric. If C2 and C4 have the same configuration, (R,R) or (S,S), the molecule is chiral and C3 is not stereogenic: this gives one pair of enantiomers. If C2 and C4 are (R,S), the molecule has a mirror plane through C3 and is meso; the Cl on C3 can then be on either side relative to the other two, giving two distinct meso diastereomers. Total stereoisomers = 2 + 2 = 4, of which 2 are meso.
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