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JEE Advanced levelNumerical answerDifficulty 3 of 3st299

The compound shown is one stereoisomer (X) of 3-chlorohex-4-en-2-ol, . Counting all configurational stereoisomers (geometrical and optical together) of this constitution, how many are diastereomers of X? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 6

The constitution has two stereocentres (C2 and C3, carrying different groups) and one stereogenic double bond (C4=C5). The molecule has no symmetry, so the total number of stereoisomers is . X itself is (2S,3S,4E). Its mirror image, (2R,3R,4E), is its enantiomer (reflection does not change /). Every other stereoisomer is neither X nor its mirror image, so the number of diastereomers of X is .
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