Survey of Organic Chemistry
Exam II - 100 points
October 22, 2004 - Dr. Howard Black
1.
(16 pts) Please provide
an acceptable name for each of the following compounds, remembering to
address stereochemistry whenever appropriate.
2. (14 pts) For each of the following four molecules, list the properties from the list on the right which best describe it. Each item on the list can be used as often as necessary, or not at all. You are penalized for incorrect as well as missing letters, so guessing is a really bad idea!!
3. (30 pts) Complete the following reactions, paying attention to stereochemical details when necessary. DO NOT give information that isn't requested! You will be asked for either the reagent(s) or the product(s) for a reaction, so don't write in both areas! If a reaction gives more than one product, draw only the major one.
2. (14 pts) For each of the following four molecules, list the properties from the list on the right which best describe it. Each item on the list can be used as often as necessary, or not at all. You are penalized for incorrect as well as missing letters, so guessing is a really bad idea!!
 |
a.
Empirical formula = CnH2n+2 b. Lowest oxidation state of the four molecules c. Is an isomer of another molecule in the list d. Empirical formula = CnH2n e. Can be made by hydration of an alkene f. More stable than the other alkene in the list g. Reacts with Na to give H2 gas h. Gives the alcohol in the list by treatment with H3O+ i. Reacts with PCC j. Would be over-oxidized by H2CrO4 k. Reacts with MCPBA |
3. (30 pts) Complete the following reactions, paying attention to stereochemical details when necessary. DO NOT give information that isn't requested! You will be asked for either the reagent(s) or the product(s) for a reaction, so don't write in both areas! If a reaction gives more than one product, draw only the major one.
4.
(20 pts) You are to
synthesize two molecules in this problem, and one of the molecules must
come from each row of the table below, using the starting material that
begins the row. In other words, starting with #1, you are to
show how to make A, B, C, or D. Then,
starting with #2, propose a synthesis of E, F, G,
or H. You may use any reagents you like, including
carbon-containing ones, as long as they contain no more than one carbon
atom. Be sure and write the letter of your target molecule where
indicated.
5.
(20 pts) Choose two (2)
of the reactions in the box, and outline their mechanisms. Be sure to
write the letter of your choices on the provided lines.
Bonus (5 pts, no partial
credit possible). Provide a mechanism for the transformation which
accounts for the
stereochemistry.
stereochemistry.