Ch. 5 - ChiralityWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Concept #1: R and S rule for Fischer Projections.

Determine location of lowest priority group:

  • If vertical, chirality is as it looks
  • If horizontal, chirality is flipped.

Determine the absolute configurations for all chiral centers.

Example #1: Determine the absolute configurations for all chiral centers.

Additional Problems
Name the following molecule.
Answer the following questions based on the compoud named.  a) Draw the Fischer projection of (2R,3S,5R)-5-bromohexa-2,3-diol.                 b) Name and draw two diastereomers of (2R,3S,5R)-5-bromohexa-2,3-diol.               c) Name and draw the enantiomer of (2R,3S,5R)-5-bromohexa-2,3-diol. 
Determine whether each statements is true or false: Rotating the Fischer projection of a molecule with a single chirality center by 90° will generate the enantiomer of the original Fischer projection:
What is the IUPAC name of the compound shown below? A) (2R,3S,4R)-3,4-dibromo-2-chloro-3-methylhexane B) (3S,4S,5S)-3,4-dibromo-5-chloro-4-methylhexane C) (2R,3S,4S)-3,4-dibromo-2-chloro-3-methylhexane D) (2R,3R,4S)-3,4-dibromo-2-chloro-3-methylhexane E) (2R,3S,4S)-2-chloro-3,4-dibromo-3-methylhexane
For each of the following pairs of molecules identify them as one of the following: constitutional isomers (I), same molecule (S), enantiomers (E), diastereomers (D), or none of the above (N).
What are the absolute configurations of these two molecules? a) S(I) and S(II) b) S(I) and R(II) c) R(I) and S(II) d) R(I) and R(II)
In the Fischer projection below determine the correct R/S designation for each chirality center [going from top (1) to bottom (3)].  
The configurations of the two stereocenters (chiral centers) in this Fischer projection are  a) 2R, 3R  b) 2R, 3S c) 2S, 3R  d) 2S, 3S
Draw the mirror images of the following molecules. Correctly identify the absolute configuration of each chiral center in both the molecules shown and their mirror images. Are any of these molecules superimposable on their mirror image?
Consider the compound below to answer the following questions:  Assign the configuration as (R) or (S) at each chiral center. Draw an acceptable regular three dimensional structure for the compound. Draw the structure of its mirror image and determine its relationship with the original molecule. Is the molecule chiral?
As shown below, compound (B) is one of the configurational isomers of (A). (a) Determine stereo‐configuration of the carbons in (B) (R, S, or none) and complete Fisher projection of (B). (C1 on the top) and cross points representing C2, C3, and C4. (b) Please fill in wedge/dash bonds and substituents in the blanks provided below to create the enantiomer (C) to the compound (B). And please also complete the drawing of two meso compounds (D) and (E) based on skeletal (A).
Circle the structure that represents (2S,3R)-2-bromo-2-chlorohex-4-yne-1,3-diol.
Determine the R and S configuration of the following compound. 
Draw the mirror image of the following molecule. 
Which statement about these Fischer projections is correct?a) I and III are enantiomers.b) II is a meso isomer.c) II and IV are identical.d) I and II are diastereomers.
Draw structural formulas for the three compounds shown below. Make sure to include all pertinent stereochemical information.
Draw Fischer projection formulas for all stereoisomers of 2,4-dimethyl-3-hexanol, giving stereochemical details for each structure. As a bonus, include which compounds are enantiomers of each other and which are diastereomers.