Total points: 20 	[Plus bonus questions, 6 pts.]

Take home test, Ch 5-9 -- but no sulfur compounds (except on bonus part); see web site for details. However, much of the material in these Ch builds on Ch 3-4. You do need basic nomenclature, properties, etc to go on. And major background topics such as polarity and hydrogen bonding are now important issues. (Bonus section may include orbital hybridization.)

DUE: Monday 3/27, start of class. For “emergency use only” You may return the test by mail (postmarked by the due date): <contact info>. (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 in a message to 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 test has been turned in.

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 (or ask me).

Test is closed book. You may supply scratch paper. You may use one page of notes, as on Test 1; 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 <contact info>, 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. I will send any test clarifications/corrections that come up to the class e-mail list.

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

Total points: 20 	[Plus bonus questions; 6 pts.]

General
•	Closed book. You may use one page of notes. You can use extra paper as needed. Otherwise, no books, models, other notes, periodic table, etc. 
•	If a question isn’t clear, please ask me about it.
•	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.)

•	Please sign the “Honor System pledge”:
	I agree to take this test according to the rules established for it.

									(-signature)

1. (2 pts.) Write a balanced equation showing the aromatic substitution reaction of one mole of chlorine (Cl2) with 1,4-dipropylbenzene, in the presence of an appropriate catalyst. Show the structures of all organic compounds in the equation.

2. (3 pts.; 1 pt. per part) In each part, show the major organic product of the requested reaction. If no reaction is expected, say so -- and briefly explain why (that is, how you can tell). Parts a-b refer to the same conditions -- the standard conditions for a simple reaction.

a. Mild oxidation of 2-heptanol.

	b. Mild oxidation of 2-methyl-2-butanol.
	
c. Treatment of 1-hexanol with (anhydrous) sulfuric acid as catalyst.	

3. (1 pt.) Consider the following structure, shown as a Fischer projection. Draw the enantiomer of this chemical, also using a Fischer projection.

       HCO
          
   HCOH
          
HOCH
          
HOCH
          
          CH2OH

4. (4 pts.) Consider 3-pentanol.
a. (1/2 pt.) What is the “degree” of this alcohol?

b. (1 pt.) Give an example of an isomer of this compound that is not an alcohol. Draw the structure. 

c. (1/2 pt.) What functional group does the O represent in your new compound (part b)?

d. (1 pt.; no credit without explanation) Which isomer (the original compound given or the compound you gave in part b) has the higher boiling point? Explain, in terms of molecular interactions. (It is not sufficient to simply state that high BP are characteristic of particular functional groups. Explain why.)

e. (1 pt.) Is it possible to have an isomer of the original compound that has a double bond? If so, draw an example. If not, explain.

5.(2 pts.) Draw the structure of 4-benzyl-3,5,5-triiodo-2-phenyloctane.

6. (6 pts.) Consider the following compound:

	

a. (1 pt.) For each O atom: What functional group does it represent? (Will not accept “alcohol”.)

b. (1 pt.; 1/2 pt. per sub-part) Mark (one example of) each of the following in the structure of the original compound. If a requested feature does not occur in this chemical, say so.

–	An acidic group.
	
–	A basic group.

The clever reader may note that parts a and b are somewhat related.

c. (1/2 pt.) The molecule contains one stereocenter. Mark it.

Now, this chemical is hydrogenated -- completely on the long side chain, but not at all on the ring system. The following parts refer to this reaction.

d. (1 pt.) Draw the product of this reaction. For now, you can ignore stereochemistry. However, I suggest you read over the following parts before drawing a structure here, so you draw it clearly enough to serve your purposes below.

e. (1 pt.) How many new stereocenters are created? Show it/them.

f. (1 pt.) Considering the information in parts b and e: How many stereoisomers of the hydrogenation product (part d) are possible? Briefly explain.

g. (1/2 pt.) The question says that the hydrogenation occurred on the side chain, but not on the rings. Why is this “reasonable”? That is, as you look at the overall structure, why might you suggest that hydrogenation would be easier on the side chain than on the ring?

7. (2 pts.) Name the following compound, shown here in a Fischer projection. (I have shown the two side groups larger, to emphasize that they are “toward you”.) Include the absolute configuration (R or S), as appropriate. Show the numbering of the parent chain. Show the ranking of the four groups attached to the stereocenter. Briefly explain the rankings and the R,S part of the name. (This question will be graded largely on the stereochemistry issues.)

    CH2CH2CH2CH2Br
    
 HCBr
    
   CH2CHCH3
       
       CH3

BONUS QUESTIONS 

B1. (2 pts.) The compound at the right, called fluorene, is an example of a polyaromatic hydrocarbon (PAH). Such compounds are significant pollution problems, and they are toxic. Although most parts of this question are phrased as chemistry questions, they are relevant to the biodegradation of this compound (and other PAHs).		

a. (1/2 pt.) Mark all non-aromatic C atoms in this structure.

b. (1 pt.) Assume that the first step in the degradation of fluorene is a simple reaction with the aromatic rings. How many distinct single step products are possible? Show them, with arrows on the structure.

c. (1/2 pt.) Now, think biology. What is the likely first step product in the biodegradation of this compound?

B2. (4 pts.). Consider again the molecule given at the start of question #6. It is repeated here, for your convenience.

Parts a-b are related and parts c-d are related, but parts a-b are independent of parts c-d.

a. (1 pt.) We have introduced some simple formulas for the number of H in a compound with a certain number of C. How do O atoms affect the H count? Why? (Suggest that you might test this with a simple example. But once you see what happens, you should be able to explain it based on chemistry -- perhaps on the periodic table.)

b. (1 pt.) By looking quickly at the structure, and not explicitly showing or counting H (or C) This chemical is short how many hydrogens from the maximum possible for the number of C? Briefly explain.

c. (1 1/2 pts.) Rank the four groups that are at the stereocenter (the one you identified in #6c), by the rules used to determine the R/S configuration. Briefly explain how you rank them. (Must have correct stereocenter. Of course, if you had incorrectly identified the stereocenter, it should become obvious at this step.)

d. (1/2 pt.) The given structure does not actually show the stereochemistry at the stereocenter. So, choose one stereoisomer. You can indicate it by modifying (or annotating) the given structure or by redrawing it here. (If you redraw it, you don’t need to draw the whole thing; just enough to make the key point clear.) Having chosen an isomer, determine whether it is R or S.

cq\bq2	(Sp 06)
3/19/06