So the question is: whether the two structures represent enantiomers or two molecules of same compound.

According to me they should be the same compound as I tried to find the R and S configuration using the CIP rules and as per that both structure came out to be S so they should be the same molecule. But the book says that they are enantiomers. Is there a misprint or have I done anything wrong.

Source: Solomons fryhle snyder organic chemistry ms chouhan chapter 4 stereo chemistry practice problem 4.12

Practice problem 5.13 in original book

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    $\begingroup$ They are different drawings of the same enantiomer of a chiral compound; an enantiomer not enantiomers. $\endgroup$
    – jimchmst
    Feb 6 at 18:57
  • $\begingroup$ Could you please include a citation to the book. And the verbatim exercise. If there is an error in the book, it will be useful for future visitors. Anyway, the shown structures are identical representations, you can rotate the paper 180° and you can almost see it. $\endgroup$ Feb 6 at 19:23
  • $\begingroup$ While the two structures are indeed a single enantiomer, a 180 degree rotation of the second structure gives the other one. A possible source of the incorrect answer is that in the rotated structure the hydroxyl lies to the left of the dotted hydrogen while in the other structure it lies to the right. If so, the "book" doesn't realize they are identical. $\endgroup$
    – user55119
    Feb 7 at 0:53


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