Enantiomers and diastereomers template

All 2² = 4 stereoisomers of 2-bromo-3-chlorobutane with R/S labels, linked as enantiomers (every centre inverted) or diastereomers (only some inverted).

What the template shows

• The four stereoisomers of 2-bromo-3-chlorobutane: two pairs of enantiomers, diastereomeric to each other
• Stereoisomers of CH₃CHBr–CHClCH₃
• Diagonal pairs, (2R,3R) / (2S,3R) and (2S,3S) / (2R,3S), are diastereomers too.
• Enantiomers are non-superimposable mirror images: every stereocentre is inverted, (2R,3R) ↔ (2S,3S).
• Diastereomers are stereoisomers that are not mirror images: only some centres differ, (2R,3R) ↔ (2R,3S).
• n stereocentres give at most 2ⁿ stereoisomers; fewer when the molecule has internal symmetry (meso compounds).
• Enantiomers share every physical property except the sign of optical rotation; diastereomers differ in melting point, solubility and NMR spectrum.
• Wedge = toward you, hash = away from you · every part of this figure is editable

Drawn with 24 atoms, 42 shapes – every one editable in MolDraw.

Sources

• Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 14 Textbook
• Eliel & Wilen, Stereochemistry of Organic Compounds, Wiley 1994, ch. 3 Textbook
• Moss, Basic terminology of stereochemistry (IUPAC Recommendations 1996), Pure Appl. Chem. 1996, 68, 2193 IUPAC