Topic 45: Synthesis of a quaternary ammonium salt by SN2 displacement involving an alkyl halide

45.1What is a quaternary ammonium salt?
 
45.2Why are quaternary ammonium salts useful? (When have use used these in lab? Why?)
 
45.3Why is direct SN2 reaction of an amine with an alkyl bromide not generally useful?
 
45.4Why does this work if what you want to form is a quaternary ammonium salt?
 

Topic 46: Synthesis of amines

46.1How can the reaction of ammonia with a primary alkyl halide to form a primary alkyl halide be designed to be successful?
 
46.2Is the use of a huge excess of ammonia to produce a primary amine a kinetic or thermodynamic strategy?
 
46.3How did Siegmund Gabriel (in 1887!) solve the problem of overalkylation in the synthesis of primary amines?
 
46.4What reagents can be used to reduce a nitro compound to an amine?
 
46.5What type of amine (primary, secondary, or tertiary) can be made this way?
 
46.6What two carboxylic acid derivatives can be reduced to amines using LiAlH4?
 
46.7What type of amine (primary, secondary, or tertiary) can be made this way?
 
46.8What is reductive amination?
 
46.9What is the formula of sodium cyanoborohydride? Why is it necessary to use this very mild reducing agent for reductive amination?
 

Topic 47: Amine basicity

47.1Which is more basic, ethylamine or diethylamine? Why?
 
47.2Which is more basic, ethylamine or acetamide? Why?
 
47.3How do you explain the difference in basicity of pyridine and piperidine?

 
47.4What are the approximate pKa values of diisopropylamine and aniline? How do you explain the difference?
 

Topic 48: Diazonium salts and azo compounds

48.1What is an aryl diazonium salt?
 
48.2How are aryl diazonium salts made?
 
48.3What are they good for?
 
48.4What is hypophosphorous acid, and why is its reaction with an aryl diazonium salt useful?
 
48.5What is azo coupling?
 
48.6How does that work?
 
48.7What are some limitations of azo coupling?
 
48.8What industry has particularly taken advantage of this chemistry?
 
48.9What health/environmental issues are particularly concerning about azo compounds? (see, for example, this report)
 
26 questions
472 questions for Organic II

472 Questions for Organic II

Dearest Student. This web page is a set of questions I call Detailed Intended Learning Outcomes For Organic Chemistry (Part II). 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 248 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)