Ch. 5 - ChiralitySee 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

The simplest test for chirality is symmetry. If a molecule has an internal line of symmetry, it is achiral

Concept #1: How and when to use the internal line of symmetry test.

  • Unfortunately, this test is only practical for rings.

This is what we call a Hawthorne Projection. It’s a way to visualize rings in 3D. It’s really easy to tell if these molecules have a plane of symmetry or not. 

Example #1: Does the following molecule contain a stereogenic center? Is it chiral?

 

This is a 2D ringed structure. It’s super easy to predict a plane of symmetry on this one. 

Example #2: Does the following molecule contain a stereogenic center? Is it chiral?

 

The plane of symmetry is allowed to split atoms! Just look for any line that can create equal images on both sides. 

Example #3: Does the following molecule contain a stereogenic center? Is it chiral?

 

Do you think TEST 1 will work well on this molecule? Why or why not?

Example #4: Does the following molecule contain a stereogenic center? Is it chiral?

 

Additional Problems
Which of the following structures do not contain a plane of symmetry? Circle all that apply.
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry.
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry.
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry.
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry.
cis-1,3-Dimethylcyclobutane has two planes of symmetry. Draw the compound and identify both planes of symmetry.
Consider the following two compounds. These compounds are stereoisomers of 1,2,3-trimethylcyclohexane. One of these compounds has three chirality centers, while the other compound has only two chirality centers. Identify which compound has only two chirality centers and explain why.  
Which of the following molecules is/are optically active:    a. I    b. II    c. V    d. I and II    e. I and V
Determine which pair of molecule(s) are optically active.    1. A and C 2. B and D 3. B and C 4. C and D 5. Three of these are optically active.
Draw the mirror image of the following molecule. 
 Identify whether each of the following compounds is chiral or achiral:
 Identify whether each of the following compounds is chiral or achiral:
 Identify whether each of the following compounds is chiral or achiral:
Indicate if the compound is chiral or achiral. 
 Identify whether each of the following compounds is chiral or achiral:
Indicate if the compounds are chiral or achiral. 
Indicate if the compounds are chiral or achiral.