Total points: 21 [Plus bonus problems, 6 pts.]	ARE YOU REGISTERED? _______
						Have you signed up for the class e-mail list: ____
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.)

1. (2 pts., 1 pt. per part) Name the following compounds, following the official (IUPAC) rules. Please show the numbering of the main chain in each case.

a. 
           Cl Cl
             \/
CH3CH2CHCH2CH2CCH3
     
     CH2CH2CH3

b. Br-/\/\=

2. (1 pt.; no credit without explanation) Petroleum refining produces a wide range of hydrocarbons. Among them are ethane and ethene (ethylene). Which (one) of these two hydrocarbons is more useful as a starting material for making a variety of chemicals in the lab? Why, in terms of the properties of these chemicals? (Ignore possible issues such as the amount of the chemicals, or the ease of purifying them from the refining mixture.)

3. (1 pt.; no credit without explanation) Which of the following two chemicals is likely to have the higher boiling point? Why, based on the structure of the molecule?

n-pentane and 2-methylbutane (isopentane)

4. (8 pts.) 
a. (2 pts.) Draw the structure of trans-1-tert-butyl-3-ethylcyclohexane, using a simple hexagon-based line formula. (Caution. Be sure it is clear. If in doubt, have me check it. Or you can annotate it.)

b. (1 pt.) Draw an isomer of the compound from part a that does not have a ring.

Parts c and d ask you to mark specific features on your structures above. Be sure to label your marked features clearly. If a requested feature does not exist in these compounds, say so.

c. (1 pt.; 1/2 pt. each) In the compound of part a, mark a primary carbon and a secondary carbon.

d. (1 pt.; 1/2 pt. each) In either compound (part a or b), mark a 90 bond angle and a 120 bond angle.

e. (2 pts.) Write a balanced equation showing the complete combustion of these compounds. 

f. (1 pt.) Draw the most stable conformation of the compound from part a -- assuming that the ring is in the chair conformation. You can use the following chair template as the basis for your drawing. For clarity, show the alkyl groups and also the H’s that are on the key C. Show them so that axial and equatorial positions are clear.

5. (2 pts.) Ectocarpene is released by the eggs of certain seaweeds to attract sperm. Ectocarpene is 6-(1-butenyl)-1,4-cycloheptadiene. Draw a structural formula for this compound. [This name includes one relatively advanced feature that you may not have seen before, but which you should be able to figure out. The side chain is itself numbered from its point of attachment.]

6. (2 pts.) Draw the structure of the following chemical: (E)-2-chloro-3-methyl-2-octene. Be sure key features are clear. Briefly explain how you determine the “E-ness” of the structure.

7. (3 pts.; 1 pt. per part) For each part, show the structure of the major organic product of the indicated reaction. If no reaction is expected, say so. Each question is intended to deal with major typical reactions.

a. Reduction (hydrogenation) of cis-2-pentene.

b. 3-propylcyclohexene + Br2 (mild conditions, no irradiation) 

c. 3-propylcyclohexene + Br2 (same conditions as part b) 

8. (2 pts.) Show how you could make 3-chloro-3,4-dimethylhexane starting from an alkene. (You choose the alkene, and you can use “standard reagents”.)

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. (2 pts.; 1 pt. per part) We have looked at the shape around neutral C atoms. Now you have seen carbocations (though officially they are not on this test), so let's explore further

In each part, explain, using the normal procedure for determining shape at a particular position. Use standard terms for describing shape. If not sure of those, give the bond angles.

a. What is the shape around a C in a carbocation? 

b  in a carbanion?

To help you visualize these Consider methane, and imagine the following (hypothetical) events		CH4  CH3+ + H-		CH4  CH3- + H+

The charge per se is not relevant to determining the shape. (Don't misinterpret that!) To determine the shape, the first thing you need to do is to ??

B2. (4 pts.) Consider a C8 hydrocarbon with only single bonds -- with each C at the corner of a cube. (If you want, look at a box-shaped object to help you visualize this.)

a. (1/2 pt.) What is the molecular formula?

b. (1 pt.) How many possible (mono)chloro derivatives are there? (This is equivalent to asking how many sets of equivalent hydrogens there are.) Explain or show -- somehow showing me that your numerical answer is not just a “guess”.

c. (1 pt.) [Probably requires that part a be correct; have me check your part a if you want.] Draw the structure of an isomer of this compound that is acyclic (non-cyclic) and has one quaternary C. (Caution. You need a strategy. Perhaps you will start with some exploration, but try to develop a strategy.)

d. (1 pt.) [Requires that part c be correct, or be of similar difficulty for this part.] Give a good IUPAC name for what you drew in part c.

e. (1/2 pt.) Suggest a good “common name” for the original compound. (It is an alkane, so the name should end in  .)

Feedback. Any comments/gripes/suggestions about the course so far??? How is the pace? (On “average”, students should spend ~6 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	6/22/03