Topic 58: Oxidation and reduction

58.1How did you define oxidation and reduction in general chemistry?
 
58.2What does it mean when we say that something is an oxidizing agent?
 
58.3What does it mean when we say that something is a reducing agent?
 
58.4How can we recognize oxidation of carbon in organic reactions? reduction?
 
58.5Why don‘t we talk about (care about) oxidation states of carbon?
 
58.6Give five examples of reactions we have studied that do not involve oxidation or reduction. Are there any that we have seen in previous chapters that DO involve oxidation or reduction?
 

Topic 59: Reduction of carbon

59.1What is the difference between homogeneous and heterogeneous catalysis? Give an example of each.
 
59.2How does the mechanism of the reaction of an alkene with hydrogen catalyzed by palladium on carbon (H2, Pd/C) result in the reaction being stereospecific?
 
59.3What are the ways to reduce an alkyne to an alkene and get preference for syn or anti addition (whichever we want)? Why do these methods work?
 
59.4What does it mean to poison a catalyst, and when might that be a good thing to do? Where have we seen something like that before -- where one reagent is too reactive, so we use a variation that just goes as far as we want it to?
 
59.5What does lithium aluminum hydride (LiAlH4) do? Why would you not want to use it with (in fact, get it it anywhere near) a protic solvent?
 
59.6LiAlH4 is quite reactive. Check out these accident reports from Stanford University Bedoukian Research. It is not at all unusual that going down the periodic table, we come to considerably more reactive elements. What other, similar but consdirably less dangerous reducing agent would you consider using BEFORE trying LiAlH4 if you were doing synthetic organic chemistry research?
 
59.7Sometime it is mentioned that aldehydes and ketones can be reduced to alcohols using hydrogen and Pd/C. While technically correct, no one ever does it this way, at least not in a typical research lab. Certainly you can reduce an alkene in the presence of a C=O in the same compound using H2 Pd/C, and nothing will happen to the C=O bond. How do organic chemists really do the reduction of a ketone or aldehyde to an alcohol?
 
13 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)