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Ch. 4 - Alkanes and CycloalkanesWorksheetSee 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
Ch. 26 - Transition Metals
IUPAC Naming
Alkyl Groups
Naming Cycloalkanes
Naming Bicyclic Compounds
Naming Alkyl Halides
Naming Alkenes
Naming Alcohols
Naming Amines
Cis vs Trans
Conformational Isomers
Newman Projections
Drawing Newman Projections
Barrier To Rotation
Ring Strain
Axial vs Equatorial
Cis vs Trans Conformations
Equatorial Preference
Chair Flip
Calculating Energy Difference Between Chair Conformations
Additional Guides
t-Butyl, sec-Butyl, isobutyl, n-butyl

For most classes all you will need to know how to do is use equatorial preference to predict the most stable chair conformation.


However, sometimes you will be required to use energetics to calculate the exact percentages of each chair in solution. This is a multistep process, so here I’m going to walk you through it from scratch. 

Calculating Flip Energy

First we have to introduce the concept of an A-value, which is simply the energy difference between the equatorial (most stable) and axial (least stable) positions.

Concept #1: Explaining how A-Values are related to cyclohexane flip energy

We can use these values to calculate how much energy it is going to take to flip a chair into its least stable form.

Note: The above chair flip in the video is slightly off. Remember that the direction of the groups (up vs. down) should not change when going from axial to equatorial or vice versa.


All the math is still correct here, but I should have drawn the groups down instead of up on the second chair. :)


[Refer to the videos below for examples of this]

Practice: Calculate the difference in Gibbs free energy between the alternative chair conformations of trans-4-iodo-1-cyclohexanol. 

Practice: Calculate the difference in Gibbs free energy between the alternative chair conformations of cis-2-ethyl-1-phenylcyclohexane.