Topic 29: Carboxylic acid structure, nomenclature, spectroscopy, and synthesis

29.1Just so you know, there is no single “IUPAC System.” We will be talking about several in this chapter and later in the book. In any case, what are the two suffixes used for naming carboxylic acids using the IUPAC substitutive nomenclature system? What‘s the difference? When do you use one or the other?
 
29.2What are the IUPAC “preferred” names for the following eight compounds: methanoic acid, ethanoic acid, propanoic acid, butanoic acid, benzenecarboxylic acid, ethanedioic acid, propanedioic acid, and butanedioic acid?
 
29.3What is meant by “principal characteristic group” in the IUPAC substitutive system? (See also Appendix B table B.1.) Why is it important in understanding how to name carboxylic acids?
 
29.4What characteristic signals do we find for carboxylic acids in IR, 1H-NMR, and 13C-NMR?
 
29.5What ways do we already know how to make carboxylic acids? Is there anything new in this regard in this chapter?
 

Topic 30: Relative acidity of carboxylic acids

30.1What is meant by the term amphoteric? [look it up] How does that apply to carboxylic acids?
 
30.2Which oxygen atom of a CO2H group is more basic — the doubly-bonded O, or the OH oxygen? Explain that.
 
30.3What is the difference between a strong acid and a weak acid? [recall general chemistry or look it up]
 
30.4How does this standard definition of “strong acid” conflict with the section heading for Section 19.7?
 
30.5How do we know that all carboxylic acids are weak acids? — That there is no such thing as a “strong carboxylic acid”? (Hint: See Appendix A. What is the strongest carboxylic acid on that list? Why would it be so strong, yet still be called “weak”? Why is it unlikely that any other carboxylic acid would be any stronger than that one?)
 
30.6Why is a carboxylic acid more acidic than phenol? Why is phenol more acidic than cyclohexanol?
 
30.7What is the inductive effect, and what does it have to do with carboxylic acid pKa?
 
30.8How does your author suggest we predict the relative acidity of substituted benzoic acids?
 
30.9Based on the pKa table below, how might we modify the claimed "rule" that "electron donating groups decrease the acidity of benzoic acid"?
grouportho pKameta pKapara pKa
NH26.974.784.92
OH2.974.064.48
OMe3.733.844.37
Me4.273.914.36
H4.194.194.19
Cl2.923.823.98
NO22.163.473.41

 
14 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)