Total points: 22 [Plus bonus problems, 5 pts.]	ARE YOU REGISTERED? _______
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General
•	Closed book. You may use one page of notes. Otherwise, no books, periodic table, models, 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.)

You may want to know the halogens are, from top to bottom of the periodic table: fluorine, chlorine, bromine, iodine.

1. (3 pts.) 
a. (2 pts.) Draw the structure (an ordinary structural formula) of cis-1-chloro-2-iodocyclohexane. Be sure that the key features are clear. 

b. (1 pt.) Draw the most stable conformation of this chemical. Assume that the ring conformation is a chair. You can use the following chair template as the basis for your drawing. For clarity, show the halogen groups and also the H’s that are on the key carbon(s). Show them so that axial and equatorial positions are clear.

	

2. (2 pts.) Draw all possible isomers of (mono)bromopropane. Name one of them.

3. (2 pts.; 1 pt. per part) Can one C atom form 2 double bonds? 2 triple bonds? In each case If yes, give an example of a compound with this feature; show the structural formula, including all the atoms. If no, explain why.

a. Two double bonds.				b. Two triple bonds.

4. (1 pt.) The graph shows the boiling points of two families of alkanes: linear (unbranched) and 2-methyl branched. The abscissa is the total number of C.

Which line is for unbranched alkanes? Explain how you can tell, based on the expected properties.

5. (2 pts.) Give an example of a common type of reaction that is typical of (almost) all classes of organic compounds, specifically including alkanes and alkenes. Use an alkene (your choice) in your example, and write a balanced equation. Include phases.

6. (4 pts.) 
a. (2 pts.) Consider the addition of HCl to 3,7,7-trimethyl-2-octene. What is the major product that is expected?

b. (1 pt.; 1/2 pt. per sub-part) Mark one secondary carbon and one quaternary carbon in your product (part a). If there are none (of a particular type), say so.

c. (1 pt.) Name the major product from part a. (Careful!)

7. (2 pts.) Consider the reaction of 3-ethyl-4-heptylcyclohexene with H2O/H2SO4. Draw the structures of the major organic reactant and product. (In other words, write an equation for the reaction, using structural formulas.)

8. (6 pts.) Consider cis-2-pentene and the product of adding chlorine to that alkene.

a. (2 pts.) Draw the structures of these two organic compounds. (That is, draw the organic reactant and product.)

b. (1 pt.) Name the addition product.

c. (1 pt.) What are the bond angles at carbon #2 of the alkene?

d. (1 pt.) Draw the structure of an isomer of the alkene that is not an alkene.

e. (1 pt.) What would happen if pentane were used in the reaction stated at the start of the question (instead of the pentene)? Same conditions -- typical of those used for the original reaction. Explain how you can tell.

BONUS QUESTIONS [Bonus questions may be harder, on more advanced material, or more open-ended. Bonus points are recorded separately, and will not normally affect course grade (except possibly in borderline cases). I encourage you to give these a try if time permits.]

•	Bonus questions are on next page.

B1. (1 pt.) An important cancer chemotherapeutic agent is cisplatin, the cis isomer of PtCl2(NH3)2. Draw the structure of cisplatin. (In this compound, the molecular geometry is square planar around the central Pt atom. Each NH3 is bonded to Pt, by a fourth N bond. All other bonding is normal.)

B2. (2 pts.) This question is based on an issue that was important in analyzing the TWA flight 800 plane crash. Consider a liquid fuel (similar to gasoline), consisting of a mixture of alkanes. For simplicity, let’s assume that the fuel contains 30% octane and 70% decane (both straight chain; dec- = 10). If you have a bottle of this fuel, some will vaporize in the container. Would you expect the vapor in the container to have the same composition as the liquid fuel (as stated above)? If not, how would the vapor composition be different -- qualitatively? Explain.

B3. (2 pts.) The structure of terpenes is consistent with them being made by the addition polymerization of isoprene (2-methyl-1,3-butadiene), C5H8. (The actual biological process is more complex, but doesn’t concern us here.) Draw a simple terpene, which would result from one such addition reaction (with no further modifications). Show the two isoprene units, and use arrows to show what is adding where. Give the molecular formula of the product (1/2 pt.). (Hint. To help visualize the addition, think about the simpler example of how polyethylene would be made.) (Several products are possible; any one of them is fine.)

B4. (1 millipoint -- but I might report the results to the Dept of Motor Vehicles) What simple organic chemical (from current chapters) was probably the inspiration for the common STOP sign? Explain.

Feedback. Any comments/gripes/suggestions about the course so far??? How is the pace? (On “average”, students should spend ~6-8 hr/wk outside of class on the course.) Use of class time? Homework? In general, what’s good, what’s not? (If this isn’t the time or place, slip me notes any time, or let’s discuss.) 	

cq\bq1	(Sp 06)
2/25/06