Relative and Absolute Configurations
High-Yield Summary
- Relative configuration compares one chiral molecule to another (used to classify enantiomers/diastereomers/identical). Absolute configuration describes one molecule's exact spatial arrangement on its own, via R/S.
- E/Z nomenclature extends CIP priority logic to polysubstituted double bonds, where simple cis/trans breaks down: same side of highest-priority groups = Z (zusammen, 'together'); opposite sides = E (entgegen, 'opposite').
- Fischer projections are 2D 'table' drawings of 3D molecules: vertical bonds point away from viewer, horizontal bonds point toward viewer. Common for carbohydrates and amino acids.
- Converting Fischer → bond-line: set up backbone from top/bottom groups; left substituents become wedges, right become dashes; flipping to standard bond-line orientation swaps every wedge/dash; verify R/S is preserved.
Assigning E or Z to a Double Bond
- 1Identify the two substituents attached to each carbon of the double bond.
- 2Assign priority to each pair by atomic number (same rule as CIP for chiral centers).
- 3Compare the positions of the two highest-priority substituents, one per alkene carbon: same side → Z; opposite sides → E.
Converting a Fischer Projection to a Bond-Line Structure
- 1Set up the backbone: top and bottom groups become the two ends of the bond-line structure, with a dot for each carbon in between.
- 2Add substituents: groups on the left become wedges (out of plane), groups on the right become dashes (behind plane).
- 3Reorient to bond-line: flipping the zig-zag backbone into standard orientation swaps every wedge to a dash and every dash to a wedge.
- 4Verify stereochemistry: re-check each chiral center's R/S using CIP to confirm configuration was preserved through the conversion.
Key Terms
- Relative configuration
- A chiral molecule's configuration described in relation to another chiral molecule — the tool for classifying enantiomers/diastereomers/identical molecules.
- Absolute configuration
- The exact spatial arrangement of one chiral molecule's atoms, independent of any other molecule, expressed via R/S.
- E/Z nomenclature
- Labels double-bond geometry for polysubstituted alkenes using CIP priority: same side of top-priority groups = Z, opposite sides = E.
- Fischer projection
- 2D 'table' representation of a 3D molecule: vertical bonds point away from viewer, horizontal bonds point toward viewer.
Common MCAT Trap
- E/Z is not the same as trans/cis by default — E/Z is based on CIP priority of the two highest-ranked substituents, which may or may not correspond to the 'same group' comparison that cis/trans relies on.
- In a Fischer projection, vertical = away from viewer, horizontal = toward viewer — reversing this convention flips every wedge/dash and inverts R/S incorrectly.
- When converting Fischer to bond-line, the reorientation flip (standard zig-zag) swaps every wedge and dash — skipping this step gives the mirror-image (wrong) stereochemistry.
Quick Recall
What's the difference between relative and absolute configuration?
In E/Z nomenclature, what does Z mean and where does the term come from?
In a Fischer projection, which bonds point toward the viewer and which point away?
When converting a Fischer projection to bond-line, what happens to left/right substituents during the reorientation flip?