Total points: 21 	[Plus bonus questions, 7 pts.]

Take home test, Ch 10-12. However, much of the material in these Ch builds on earlier material.

A copy of (part of) Fig 11.1 is attached, along with the structure of -D-glucose.

DUE: Monday 8/11, start of class. For “emergency use only” You may return the test by mail (postmarked by the due date): <>. (Do NOT send by any method that requires my signature to pick it up.)

•	If I learn of corrections or clarifications to test questions, I will distribute them via the class e-mail list.

The general idea is that a take home test is just like a test in class, except that you determine the time and place to take it.

Do not open the test until you are ready to start taking it. Opening the test marks the end of your study time and the beginning of test time. Before beginning the test, you may study as much as you wish, and in any way. You may study with others, so long as no one involved has yet opened the test. You may not discuss the test with others (except me) until after the due time.

This test is similar to other tests in this course (including the samples). Try to resolve doubts about the meaning of test questions by considering them in the context of this course. If you feel there are ambiguities in a question, state any assumptions you make.

Test is closed book. You may supply scratch paper. You may use one page of notes, as before; see web site for details. Except for that, you may NOT use books, handouts, models, class notes, other outside sources, etc.

Estimated time: 1-2 hours. It is not a timed test. Take the time you need to do it well. So long as you feel you are being productive, you are welcome to continue. (That also means you need to know when to stop.) I would appreciate it if you would note how long you took.

You should try to take the test “straight through” in one session. However, you may seek clarification of test questions at a reasonable time after your primary session. This may include asking me about test questions when you bring it to class.

Feel free to call me at home (<>), either in preparation for the test or if you need clarification of questions during the test. I will “guarantee” phone availability Sunday evening 7-9 pm. If you leave messages on my answering machine, please leave guidance as to how late I can call. 

•	Please SIGN the “Honor System pledge” (next page).

Total points: 21 	[Plus bonus questions; 7 pts.]

General
•	Closed book. You may use one page of notes. Except for that, no books, models, other notes, periodic table, etc. (Some Figs are attached, p 5.)
•	Some questions request a simple answer and an explanation. It’s the explanation that is important. No credit for answer without a requested explanation. 
•	In naming compounds, IUPAC names are preferred, but valid common names will be accepted. (A name will be graded based on the compound you show.)
•	Unless specifically noted/relevant Structures of sugars (and their derivatives) should be shown in the linear form, using Fischer projections.
	
•	Please sign the “Honor System pledge”:
	I agree to take this test according to the rules established for it.
									(-signature)

1. (2 pts.; 1 pt. per part; no credit without explanation) Each part below lists two compounds. In each part, which (one) of these two is likely to have the higher boiling point? Why, based on the structure of the molecules? (Assume that the masses are not significantly different.)

a. ethanal and ethanol

b. 1-butanol and propanoic acid

2. (1 pt.; no credit without explanation) The Fig shows a 2-ring structure, produced by certain bacteria. Which (one) of those two rings is most closely related to a sugar (i.e., is a simple modification of a sugar)? Explain how you can tell (one key functional group), and explain how it is also different from a simple sugar (also one key functional group).

3. (1 pt.)  Fullerene is the C60 form of pure carbon, sometimes called buckyballs because of the soccer ball (geodesic dome) shape. Recently, scientists have succeeded in attaching sugar molecules to fullerene. Discuss the solubility in water of these two molecules: the plain C60 fullerene and the fullerene derivative with sugar attached. 

4. (2 pts.)  Some bacteria make a polyester from 3-hydroxybutanoic acid (often called -hydroxybutyric acid). Write a balanced equation for making a dimer by condensing two molecules of the monomer. Include structural formulas for the organic chemicals in the reaction. (For simplicity, assume that the given compound is the actual main reactant.)

5. (1 pt.) A major metabolite of nicotine (shown below) in the body is made by oxidation of a ring C right next to the aliphatic (non-aromatic) N to a carbonyl group. 

a. (1 pt.) Draw this oxidation product.

b. (no points, because this is a bit ahead of test coverage) What new functional group is created?

6. (4 pts.; 1 pt. per part) In each part, show the major organic product of the indicated reaction. Give the structure. If no reaction is expected, say so, and briefly explain why.

a. Reduction of cyclohexanone with NaBH4.

b. Mild oxidation of cyclohexanone.

c. Reaction of ethanoic (acetic) acid with a strong base.

d. Reaction of pentanoyl chloride (the acyl chloride of pentanoic acid) with 2-butanol.

7. (3 pts.) Bacteria of the genus Mycobacterium are responsible for some serious human diseases, including tuberculosis and leprosy. Bacterial toxins have not been identified for those diseases. However, recently a mycobacterial toxin for Buruli ulcer was found. The compound has the following structure, where R1 and R2 are complex groups that do not concern us here.

a. (2 pts.) Identify two (reactive) functional groups in this compound. Show them on the structure, and describe them using standard terminology. (I will not accept “carbonyl”; be more specific.) (As noted above, ignore the R groups.)

b. (1 pt.) Draw the product(s) of acid hydrolysis of this compound. (Draw the key parts carefully. You don't need to repeat the entire molecule.) (You can answer this in the space above.)

8. (3 pts.) You have a compound with the molecular formula C5H10O. It does not react with Br2. It reacts with mild oxidizing agents; the product is an acidic compound. 

a. (2 pts.) For each piece of evidence given, tell what you learn from it. If relevant, take into account how this piece of evidence affects what you learned in steps listed earlier.

- the formula (specifically, the H count)

- no reaction with Br2

- reaction with mild [O]

	- product of above reaction is acidic.

b. (1 pt.; must agree with your own explanation in part a.) Draw the structure of a compound that fits all of the given information.

9. (4 pts.; 1 pt. per part) Algin is a polysaccharide isolated from (certain) algae and used as a thickener in food products. It is also produced by some bacteria, especially in the lungs of cystic fibrosis patients. Algin is a co-polymer of D-mannuronic acid and its 5-epimer. This question explores some of the structural issues in algin.

a. Draw the 5-epimer of D-mannose. Use a Fischer projection.

b. Name the sugar that you drew in part a. Use the common name for the sugar; the name must account for the proper stereoisomer.

c. Draw D-mannuronic acid. (Uronic acids are due to oxidation at the 6-position.) Use a Fischer projection.

d. Assume for this part that you have the structures of the two sugar monomers that are found in algin. However, you still do not have enough information to describe the structure of algin? Why not?

	At right: 
-D-glucose	

   CHO
       
 H-C-OH
       
 H-C-OH
       
 H-C-OH
       
 H-C-OH
       
   CH2OH

D-(+)-
allose
	   CHO
       
HO-C-H
       
 H-C-OH
       
 H-C-OH
       
 H-C-OH
       
   CH2OH

D-(+)-
altrose
	   CHO
       
 H-C-OH
       
HO-C-H
       
 H-C-OH
       
 H-C-OH
       
   CH2OH

D-(+)-
glucose
	   CHO
       
HO-C-H
       
HO-C-H
       
 H-C-OH
       
 H-C-OH
       
   CH2OH

D-(+)-
mannose
	   CHO
       
 H-C-OH
       
 H-C-OH
       
HO-C-H
       
 H-C-OH
       
   CH2OH

D-(-)-
gulose
	   CHO
       
HO-C-H
       
 H-C-OH
       
HO-C-H
       
 H-C-OH
       
   CH2OH

D-(-)-
idose
	    CHO
        
  H-C-OH
        
 HO-C-H
        
 HO-C-H
        
  H-C-OH
        
    CH2OH

D-(+)-
galactose
	   CHO
       
HO-C-H
       
HO-C-H
       
HO-C-H
       
 H-C-OH
       
   CH2OH

D-(+)-
talose
	
BONUS QUESTIONS. Need not be done in same session; be reasonable, but no new studying. 

B1. (2 pts.) Describe how you could make isopropyl acetate (prop-2-yl ethanoate) from hydrocarbons (your choice). List a series of steps that you would use. (Show the major organic reactants and products in each step. You need not write balanced equations. The emphasis here is on the logical design of the synthesis, not the details of the steps.)

B2. (1 pt.) Draw the structure of the compound obtained by inserting a krypton between the C and H at one end of ethyne. Assume that the Kr forms two bonds.

B3. (3 pts.) 
a. (2 pts.) Draw the structure of the ester formed by chrysanthemumic acid [2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylic acid] and 4-hydroxy-3-methyl-2-(2,4-pentadienyl)cyclopent-2-enone.

b. (1 pt.) The ester in part a has an important (useful) effect. One thing organic chemists do with an interesting compound is to make derivatives, to try to find one that is better. Propose a simple, one-step derivative of this ester that you know how to make. Indicate how you would make it; be sure to say whether you would carry out the modification before or after ester formation (if it matters).

B4. (1 pt.) Mark all the stereocenters in the structure of the Buruli toxin, shown in question #7. (Mark the structure given there.)						cq\bq3	8/3/03