The correct statement(s) about the compound H_3C(HO)HC - CH = CH - CH(OH)CH_3 (X) is(are)

JEE Advanced 2009 Chemistry question

The correct statement(s) about the compound \mathrm{H_3C(HO)HC{-}CH{=}CH{-}CH(OH)CH_3} (X) is(are)

(A)The total number of stereoisomers possible for X is 6Correct
(B)The total number of diastereomers possible for X is 3
(C)If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4
(D)If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2Correct

Answer: (A),(D)

Solution

X (hex-3-ene-2,5-diol) has two identical stereocentres (C-2, C-5) and a C=C that can be cis or trans. For each geometry the two stereocentres give (R,R), (S,S) and the meso (R,S) form: 3 stereoisomers, so in total 2 × 3 = 6 (A true). For the cis (or trans) isomer, the

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Question ID VK-037682