Why does butane-2-3-diol have 3 stereoisomers? I count 2 chiral centers I checked somewhere else where...

Why does butane-2-3-diol have 3 stereoisomers? I count 2 chiral centers

I checked somewhere else where they did somethin like 2ⁿ-1. Is this because there is a plane of symmetry? is there a way to know when a molecule will have 3 instead of 4 stereoisomers?

I know there are three because the 4th stereoisomer is identical to one of the other stereoisomers.

Thank you.

Expert Solution

Hi yes theoretically 4 stereoisomers possible for butane-2-3-diol. Since it has 2 chiral centers and according to 2ⁿ formula = 2² = 4. But one of the isomer of butane-2-3-diol has an internal plane of symmetry and also when you rotate that partcular isomer by 180^o in-plane (not in 3-dimensional just rotate molecule on a 2d paper clock-wise or anti-clockwise) you will get mirror image isomer, hence those two are considered as one only. If rotation does not give mirror images then that pair is enantiomeric. This isomer is said to be meso-isomer and is optically inactive due to internal plane of symmetry.

Hope this helped you!

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queen_honey_blossom answered 2 years ago

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