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JEE Main 2019 · Chemistry · General Organic Chemistry and Isomerism · hard

The total number of stereoisomers (including meso forms) of pentane-2,3,4-triol, CH3CH(OH)CH(OH)CH(OH)CH3, is

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The total number of stereoisomers (including meso forms) of pentane-2,3,4-triol, CH3CH(OH)CH(OH)CH(OH)CH3\mathrm{CH_3CH(OH)CH(OH)CH(OH)CH_3}, is
  1. A. 4
  2. B. 2
  3. C. 3
  4. D. 8
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Answer: (A) 4

Three carbons, C-2, C-3, C-4, bear OH\mathrm{OH}. C-2 and C-4 are constitutionally equivalent, so 23=82^3 = 8 overcounts. When C-2 and C-4 are (R,R)(R,R) or (S,S)(S,S), C-3 has two identical-descriptor arms and is not a stereocentre: this gives the enantiomeric pair (2R,4R)(2R,4R)/(2S,4S)(2S,4S) = 2 isomers. When C-2 and C-4 are (R,S)(R,S), C-3 is pseudoasymmetric, giving two achiral meso forms (3r3r and 3s3s). Total =2+2=4=2+2=4.
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