Stereochemistry - 2 Different Stereocenters CH3 (S) Br H HO...

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Unformatted text preview: 2 Different Stereocenters CH3 (S) Br H HO OH Br H3C H (S) (S) (S) (S) (S) Br H enantiomers CH3 Br H (R) (R) Br (R) (R) H OH A CH3 CH3 B OH H H3C Br (R) (R) OH H CH3 eclipsed form of A H OH CH3 eclipsed form of B diasteromers diastereomers diastereomers Br (S) (R) CH3 H H OH (S) CH3 Br OH enantiomers Br HO (R) (S) Br (R) (S) H H (R) C Br H3C H (S) (R) CH3 CH3 OH D H OH CH3 eclipsed form of C H H3C Br (R) (S) Enantiomers Diastereomers Meso Identical Superimposable Mirror Images Optically Active* Yes No Yes No Yes Yes No Yes No Yes No Yes *as pure compounds OH H CH3 eclipsed form of D If we had a mixture of the above compounds and picked out two random molecules we would get three different possibilities. A/B and C/D are non-superimposible exact mirror images: ENANTIOMERS A/C, B/C, A/D, B/D are non-superimposable but are not mirror images: DIASTEREOMERS A/A, B/B, C/C, D/D are superimposable but not mirror images:IDENTICAL 2 Identical Stereocenters Br (S) (S) CH3 H Br Br (S) (S) Br H CH3 enantiomers Br H (R) (R) Br (R) (R) H Br Br H3C H E CH3 CH3 F Br H H3C Br (R) (R) Br (S) (S) H CH3 eclipsed form of E H Br CH3 eclipsed form of F diasteromers diastereomers diastereomers extra internal mirror plane CH3 (R) Br H H Br Br H3C H (S) (R) (S) CH3 Br (R) (S) Br (R) (S) (S) Br Br H H (R) meso Br G H Br CH3 CH3 CH3 Br G' H H3C Br (R) (S) Enantiomers Diastereomers Meso Identical Superimposable Mirror Images Optically Active* Yes No Yes No Yes Yes No Yes No Yes No Yes *as pure compounds Br H CH3 eclipsed form of G eclipsed form of G' If we had a mixture of the above compounds and picked out two random molecules we would get four different possibilities. E/F are non-superimposible exact mirror images: ENANTIOMERS E/G, E/G', F/G, F/G' are non-superimposable but are not mirror images: DIASTEREOMERS E/E, F/F are superimposable but not mirror images: IDENTICAL G/G', G/G, G'/G' are superimposable and are mirror images, this is a special case where two molecules are exactly the same and have an internal mirror plane and are MESO. ...
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This note was uploaded on 04/03/2010 for the course CHE 118A 26193 taught by Professor Lievens during the Winter '09 term at UC Davis.

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Stereochemistry - 2 Different Stereocenters CH3 (S) Br H HO...

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