How many compounds shown below are chiral?
(I) (II)
(III) (IV)
(V) (VI)
(VII) (VIII)
(IX) (X)

Question

How many compounds shown below are chiral? (I) (II) (III) (IV) (V) (VI) (VII) (VIII) (IX) (X)

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Ans. (A)

Sol. The chiral compounds are (II), (VI), (IX) and (X) - four in all. (II) is (2R,4R)-pentane-2,4-diol (no plane of symmetry); (VI) is trans-1,2-dimethylcyclopentane; (IX) has no plane, axis-improper symmetry or centre of symmetry; (X) is trans-1,2-dichloro-1,2-dimethylcyclopentane. (I) has no stereogenic centre; (III), (IV) and (V) each have a plane of symmetry; (VII) and (VIII) each have a plane of symmetry (all-cis / opposite-pair methyl pattern on the 1,4-dione ring), so they are achiral.

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