Detailed ILOs for Organic I

Topic 53: Nomenclature of alkynes


53.1	How is the nomenclature of alkynes similar to that of alkenes?


53.2	What if a compound is both an alkene and an alkyne? An alkyne and an alcohol? All three?


53.3	What is a terminal alkyne? And what is so special about that?

Topic 54: Synthesis of alkynes


54.1	How can an alkene be converted to an alkyne in two synthetic steps?


54.2	How can an alkyne be made from an alcohol in three synthetic steps?

Topic 55: Reactions of alkynes - electrophilic addition of HBr, H₂O, and Br₂


55.1	An alkyne can react with two equivalents of HBr. When it does so, both bromine atoms end up on the same carbon. How do you explain that observation?


55.2	It is possible to stop this reaction after just one equivalent of HBr has added. What does that tell us about the relative reactivity of HBr with alkenes vs. alkynes? (Or at least, vinyl bromides vs. alkynes?)


55.3	What do the following terms mean? ketone, aldehyde, enol, tautomer, tautomerization.


55.4	How is it that the acid-catalyzed addition of H₂O to an alkyne leads to a ketone or aldehyde (depending upon the location of the alkyne in the carbon chain)?


55.5	The acid-catalyzed addition of H₂O to an alkyne is not a very fast process. Somewhere along the way in the history of chemistry it was discovered that adding mercury(II) salts (such as HgSO₄) promoted the reaction. How does that work, do you suppose? Can you propose a mechanism for that?


55.6	Br₂ is a noxious highly toxic fuming liquid. It could be argued to be anything but green (in fact, it's actually blood red in color). In 2007, chemists in India reported in the journal Green Chemistry a greener alternative for the bromination of alkynes. What was their discovery? Looking at their data (Table 2), what stereochemistry (cis vs. trans) did they observe? What was the determining factor in whether the reaction was stereoselective or not?

Topic 56: Hydroboration/oxidation of alkynes


56.1	Hydroboration of alkynes proceeds about the same as for alkenes. But BH₃ cannot be used for terminal alkynes. What do you think the problem could be? What is the solution to that problem? (web research)


56.2	The end result of hydroboration/oxidation of an alkyne is not an alcohol. What is it?

Topic 57: Reactions of acetylides


57.1	What is an acetylide anion?


57.2	What two bases are commonly used to form acetylide anions? What is so special about these bases?


57.3	How are acetylide anions particularly useful in organic chemistry?

16 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!