Topic 36: Substitution - Factors influencing substitution processes - the nucleophile

36.1 How are basicity and nucleophilicity related to thermodynamics and kinetics?
 
36.2What characterizes a “good” nucleophile? Examples?
 
36.3Why are negatively charged nucleophiles (Cl–, CN–, RC≡C–) generally more reactive than neutral nucleophiles, such as H2O, CH3OH, NH3)?
 
36.4Why are negatively charged species rarely the nucleophile in SN1 reactions?
 
36.5What is solvolysis? Which mechanism, SN1 or SN2, is it more closely associated with? Why?
 

Topic 37: Substitution - Factors influencing substitution processes - the solvent

37.1What does aprotic mean?
 
37.2What are several examples of protic and aprotic solvents?
 
37.3Why might the choice of an aprotic solvent make an SN2 reaction more likely to happen, whereas choice of a protic solvent would slow it down?
 
37.4Why is it common to use protic solvents for SN2 reactions even though they are not as “good” solvents for that type of reaction?
 
37.5Why does the order of reactivity of halide nucleophiles reverse in going from a protic to aprotic solvents?
 
37.6What is the “catch” in relation to using protic solvents in SN1 reactions?
 
37.7Why is a protic solvent necessary for a solvolysis reaction?
 
12 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)