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

Since these molecules come up often in exams, it’s a good idea to just memorize a few simple rules for them. 

Concept #1: Three types of disubstituted cycloalkanes 

1. gem-disubstituted

2. para-disubstituted

3. middle-disubstituted

Cis-1,2-Disubstituted Cyclohexane

Concept #2: Cis-1,2-Disubstituted Cyclohexane: A controversial exception.

Because cyclohexane has axial and equatorial positions, some professors will have different definitions of whether this is chiral or not.

  • Textbook Answer (I agree with this one) = Achiral
  • Some wacky professors = Chiral due to axial/equatorial positions.

Note: I’ve had an Organic Chemist from Yale argue with me that it was chiral. So just check with your prof!

Is the following molecule chiral?

Example #1: Using TEST 3, is the following molecule chiral?

Is the following molecule chiral?

Example #2: Using TEST 3, is the following molecule chiral?

Is the following molecule chiral?

Example #3: Using TEST 3, is the following molecule chiral?

Is the following molecule chiral?

Example #4: Using TEST 3, is the following molecule chiral?