Topic 31: Properties of carboxylic acid derivatives

31.1Identify the functional groups: carboxylic acid, acid chloride, anhydride, ester, amide, nitrile.
 
31.2What does the prefix “anhydro” always mean in chemistry? How does that relate to the name “anhydride”?
 
31.3What are the three types of amides, and what characterizes them as such?
 
31.4What is a lactone? a lactam?
 
31.5What is the order of reactivity of acid chloride, anhydride, ester, amide toward nucleophiles? What explains this ordering?
 

Topic 32: Nomenclature and spectroscopy of carboxylic acid derivatives

32.1What are the various suffix changes for acid chlorides, anhydrides, esters, and amides?
 
32.2Both esters and amides have the added complication of groups attached to O or N. How does the IUPAC system handle this?
 
32.3The NMR and IR spectra of carboxylic acid derivatives are similar to those of carboxylic acids except for what one missing peak?
 
32.4What makes the IR spectrum of an anhydride unusual?
 

Topic 33: Reactions of acid chlorides and anhydrides

33.1The reactions of acid chlorides and anhydrides are very similar. What is the one difference?
 
33.2Why are two equivalents of an amine required for the formation of an amide from an acid chloride or anhydride?
 
33.3Let‘s say the amine you were using was actually pretty expensive. Maybe it has taken you two months to make it. How could you still make an amide using it, but avoid throwing away half of it? (two ways — for one, Google acid chloride to amide and check images; for the other, think about what you have done in lab this semester for work-ups.]
 
12 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)