Topic 13: Alkane Conformation - Cyclohexane

13.1What is the lowest-energy conformation of cyclohexane called? Describe it in detail using words, not pictures, if you can.
 
13.2What is the boat conformation, and why is it so much higher in energy than the chair conformation?
 
13.3What do the terms cis and trans mean in relation to ring systems in organic chemistry? Where have you seen them used as prefixes in standard English?
 
13.4Explain the terms equatorial, axial, and 1,3-diaxial in relation to the cyclohexane chair conformation.
 
13.5How do the ideas of gauche and anti in relation to butane also relate to cyclohexane, particularly when comparing structures with different substituents, such as 1,2-dimethylcyclohexane or 1,3-dimethylcyclohexane?
 
13.6Describe what a “ring flip” is, and how to draw one on paper. Using a plastic model, can you convert it from one chair to the other without going through the boat conformation?
 
13.7Can you draw a cyclohexane chair and its substituents such that a professional chemist can understand what you are describing?
 
13.8Given a cyclohexane derivative structure, can you predict which of the two possible chair conformations is the more favorable?
 
8 questions
364 questions for Organic I

364 Questions for Organic I

Dearest Student. This web page is a set of questions I call Detailed Intended Learning Outcomes For Organic Chemistry (Part I). Some time ago I asked myself, "Bob, what do you think are the key questions that you hope students will be able to answer after taking Chemistry 247 at St. Olaf College?" So here you have them. Some are very simple; some require more thought. All are good questions to be thinking about as you read, discuss, and master the practical aspects of organic chemistry. They are discussion starters and review tips. There are no answers here (though there are some clues). The questions are here to help you focus on what's important (to me, at least!) and organize your learning process. The questions are grouped into topics. Bite-size chunks. Take them a few at a time. Don't feast on them all at one sitting!

(preliminary version 2021.01.15 feeback: Bob Hanson)