Topic 14: Stereochemistry - Terms

14.1What does it mean that two compounds are constitutional isomers?
 
14.2What does it mean that two compounds are configurational isomers?
 
14.3What if I told you that I think that configurational isomers are just as different from each other as constitutional isomers? Would you argue for or against this position?
 
14.4A molecule is chiral if and only if what?
 
14.5What does the prefix “a” mean in English, as in asymptomatic? Why is that relevant to this discussion?
 

Topic 15: Stereochemistry - Enantiomers and Stereogenic Centers

15.1What is an enantiomer?
 
15.2Is the following statement true or false? “A molecule is achiral if and only if it is its own enantiomer.”
 
15.3What is a stereogenic center? What are its characteristics exactly?
 
15.4How do organic chemists distinguish stereogenic centers when drawing skeletal structures?
 

Topic 16: Stereochemistry - The Cahn-Ingold-Prelog System (R and S)

16.1How is priority assigned in the “CIP” system?
 
16.2In this system, which has higher priority - #1, or #4?
 
16.3How is priority “read” on a drawing, leading to a designation of R or S?
 
16.4What is the special rule for alkenes and alkynes?
 
16.5How do these rules lead to a “sensible” assignment of priorities?
 
16.6What do you do if the #4 group is not in the back (without redrawing the structure)?
 
15 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)