Total points: 21 	[Plus bonus questions, 6 pts.]

Take home test, Ch 5-9 -- but no elimination or acidity reactions; 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 includes orbital hybridization.)

DUE: Monday 7/21, 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 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 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 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 hour. 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. (It’s also ok to come back and work on the bonus section after your primary session with the main part of the test.)

Feel free to call me (<>), 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: 21 	[Plus bonus questions; 6 pts.]

General
•	Closed book. You may use one page of notes. Except for that, no books, models, other notes, periodic table, etc. 
•	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. (3 pts.; 1 pt. per part, no credit without explanation) In parts a & b you are given two compounds. Tell which (one) of the two is likely to be more soluble in water, and explain your prediction based on the structure of the molecule. These two parts are independent.

[You may know the solubility of some of these compounds. Knowing the solubility may guide you to a reasonable answer. However, knowing a specific fact such as solubility is not an acceptable explanation.]

a. decane and 2-decanol

b. 2-propanol and 2-decanol

c. Parts a & b refer to three chemicals. Which one of those three would you expect to have the highest boiling point? Why? (A complete explanation must refer to two distinct features of these chemicals.)

2. (2 pts.) Draw the main product of reacting 3-ethyl-1,4-pentanediol with an oxidizing agent that selectively oxidizes secondary alcohols.

3. (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.)

    H
    
 ICCH=CH2
    
   CH2CH2CH2I

4. (4 pts.) 
a. (2 pts.) Name the compound shown at the right. Show the numbering of the parent chain. (For this part, ignore the stereochemistry.)

The following parts are independent of part a.

b. (1 pt.) Mark all stereocenters in the structure.

c. (1 pt.; requires that part b be correct or close; no credit without explanation) Based on your answer to part b, how many stereoisomers of this compound are there? Briefly explain how you figure it out.

5. (2 pts.) Choose one of the molecular formulas shown below. For that formula, draw all possible isomers and tell what the main functional group is in each. When relevant, state the “degree” (primary etc) of the functional group. (Hint: How many ways can you draw the C skeleton? Then, how many ways can you insert an O?)

C3H8O or C8H18O

6. (1 pt.) The following list of three chemicals contains two errors. What are they? Briefly note how you can tell that the given information is incorrect.

(R)-(+)-2-pentanol	(S)-(+)-2-pentanol	(R)-3-pentanol

7. (3 pts.; 1 pt. per part) 
a. Give an example of a chiral hydrocarbon. Draw the structure. Mark the stereocenter(s).	b. Give a proper IUPAC name for the compound that you drew in part a. (You can ignore the chirality in assigning the name.)	

c. Draw the structure of a non-chiral isomer of the compound you drew in part a.

8. (2 pts.) Write a balanced equation showing the reaction of nitric acid with an aromatic ring, in a substitution reaction. (Assume appropriate conditions.) In such a reaction, nitric acid behaves as HO-NO2. Show the structures of the organic compounds in the equation.

9. (2 pts.; 1 pt. per part) Polystyrene is a plastic. Common lab petri dishes are made of polystyrene.

a. Styrene is phenylethene. Draw the structure of styrene.	b. (no credit without explanation) Would you expect the polymer polystyrene to be hydrophobic or hydrophilic? Why?

BONUS QUESTIONS. Need not be done in same session; be reasonable, but no new studying. Next page.

B1. (4 pts.) 
a. (1 pt.) Draw the structure of 1,2-propadiene (common name allene). Show all the atoms and bonds explicitly.

b. (1 pt.) What is the orbital hybridization at the central carbon? What kind of orbital is involved in each bond (from this atom)? (Careful. Think out what it needs to be to give this structure. Note that parts c and d are related. But you may be able to do those without this part.)

c. (1/2 pt.) Is free rotation possible between the C atoms? Explain.	

d. (1/2 pt.) This compound contains two  bonds. What is the angle between them (between the  bonds)? (Note that this question is not about an ordinary bond angle between atoms.)

e. (1 pt.) How many stereoisomers are possible for 1-bromo-3-chloro-1-iodopropadiene? [That is, how many isomers are there that would include the indicated name. Not interested in constitutional (structural) isomers.] Explain.

B2. (2 pts.; 1 pt. per part) In the following parts, assume reaction with one mole of Br2. The two parts are somewhat independent.

a. (no credit without explanation) What would be the major product(s) of bromination of 1,3-dimethylbenzene (m-xylene)? Explain.

b. Which dimethylbenzene isomer would give only one product in that reaction? Draw the starting isomer and that product. (Here, “dimethylbenzene” refers to a compound that properly includes that word in the name.)

cq\bq2	
7/12/03