Topic 53: Fischer projections and stereochemistry

53.1What is a Fischer projection? What aspects are critical in drawing it?
 
53.2How is a Fischer projection representable as wedges and dashes?
 
53.3What is the easiest way to assign R or S to a stereocenter represented by a Fischer projection?
 
53.4What happens to the chiral designation if a Fischer projection is rotated 90o? 180o?
 
53.5What do the designations D and L mean?
 
53.6Why are D and L more useful than R and S in carbohydrate chemistry?
 
53.7What is the easiest way to tell a D sugar from an L sugar?
 
53.8What is the structure of D-glyceraldehyde?
 

Topic 54: Carbohydrates: D-aldoses and D-ketoses

54.1What is the general formula of a carbohydrate?
 
54.2Where does this name come from?
 
54.3What is an aldose?
 
54.4What is a ketose?
 
54.5What are the structures of D-erythrose and D-threose?
 
54.6What is an easy trick to remembering which is which?
 
54.7What is the structure of D-ribose?
 
54.8Where have you of something-“ribo”-something before?
 
54.9What is the structure of D-glucose?
 
54.10Structurally, relative to D-glucose, what is notable about D-mannose and D-galactose?
 

Topic 55: Cyclic hexoses: pyranose and furanose forms, anomeric centers

55.1What is a pyranose?
 
55.2What is an anomeric center? an anomer?
 
55.3What is the difference between α-D-glucopyranose and β-D-glucopyranose?
 
55.4What is so special about the β-D-glucopyranose structure?
 
55.5Are sugars generally found in the open form, the α-pyranose form, or the β-pyranose form?
 
55.6What is a furanose? A ribofuranose? The compound 2-deoxyribofuranose?
 

Topic 56: Haworth projections

56.1What is a Haworth projection? What aspects are critical in drawing it?
 
56.2Why is it generally unnecessary to show hydrogens on carbon on a Haworth projection?
 
56.3When would a Haworth projection be more useful than a Fischer projection?
 
56.4What‘s the trick for translating from a Fischer projection to a Haworth projection?
 

Topic 57: Glycosides

57.1What is a glycoside?
 
57.2What is a glycopyranoside? a glycofuranoside?
 
57.3What is wrong with the mechanism in your book (i.e. extremely unlikely)? [Hint: what does “HCl in EtOH” mean?]
 
57.4What does hydrolysis mean?
 
57.5Why are acidic conditions necessary both for the formation of a glycoside and for its hydrolysis?
 
57.6What four products are formed in the process of glycoside formation?
 

Topic 58: Amino acids

58.1What are the names and structures of the 20 common amino acids?
 
58.2What are the four common amino acids have simple alkyl side chains? What role does this play in protein structure and folding?
 
58.3What are the two common amino acids with side chains that are carboxylates? What special roles do they play in protein folding and catalysis?
 
58.4What are the two common amino acids with side chains that are amides? Why do these two amino acids not play particularly notable roles in enzyme catalysis?
 
58.5What are the two common amino acids that are positively charged at pH 7? What special roles do they play in protein folding and catalysis?
 
58.6What are the four common amino acids that are alcohols or sulfides? What special roles do they play in protein folding and catalysis?
 
58.7What are the four common amino acids have aromatic side chains? What special roles do they play in protein catalysis?
 
58.8What is so special about glycine?
 
58.9What is so special about proline?
 

Topic 59: Peptides and their synthesis

59.1What is a peptide?
 
59.2What are two important characteristics of the peptide bond?
 
59.3What do we mean by N-terminus and C-terminus? In Ala-Gly-Ser, where is the N-terminus, and where is the C-terminus?
 
59.4Which is favored in peptide bonds, the s-cis or s-trans conformation? Why?
 
59.5What is special about a peptide bond that involves the proline nitrogen?
 
59.6What is a reliable way to make a dipeptide? (List the necessary reaction steps.)
 
59.7Explain the structure and utility of the boc and fMoc protecting groups, including what the are for and the conditions for their addition and removal.
 
59.8How is a benzyl protecting group for an alcohol or carboxylic acid generally removed?
 
59.9What is DCC? How does it work, and why is it used in peptide synthesis?
 

Topic 60: Automated peptide synthesis

60.1What is the fundamental idea behind automated peptide synthesis that allows it to be successful?
 
60.2What is the sequence of steps in the method invented by Bruce Merrifield that earned him the Nobel Prize in Chemistry in 1984?
 
60.3How does the reality of organic synthesis limit automated peptide synthesis?
 

Topic 61: Fatty acids and derivatives

61.1What is the actual definitiion of lipid? What sort of lipids do biologist typically mean when they refer to a lipid?
 
61.2What is a fatty acid?
 
61.3What Is the distinction among staturated, monosaturated, and polysaturated fatty acids? And why is that important?
 
61.4What is a wax? Why would a wax be so good at surface such as a painted car or a piece of furnature?
 
61.5What is a triacylglycerol? What two terms to chefs use when referring to triacylglycerols?
 
61.6What is a phospholipid? What important role do phospholipids play in virtually all biological systems?
 
61.7What is an eicosanoid? (What does eicosa mean in chemical nomenclature?)
 
61.8What is a prostaglandin? What critical role do prostaglandins play in the human body?
 

Topic 62: Terpenes and steroids

62.1What is a terpene?
 
62.2Why are terpenes typically multiples of five carbons?
 
62.3What major industries are based on isolating, mixing or reacting terpenes?
 
62.4What is a steroid? What role in the human body do steroids play?
 
67 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)