Cover Sheet! EXAM 2b CHEM230-001 8-Week Summer 2005 PRINT your name legibly on the line below. PRINT your student id number on the line below.2005 8-week summer Organic Chemistry CHE230-001 EXAM 2b Name: _______________________________ Student ID No:_____________________ Place your student identification on your desk. A proctor will come around to check your ID. Put your name and number on your test? It is critically important that your answers be written in a clear, unambiguous manner. Answers in which your intentions are unclear may not receive credit. SHOW YOUR WORK! Problem Number Points possible Score 1. 15 _____ 2. 20 _____ 3. 30 _____ 4. 15 _____ 5. 10 _____ 6. 10 _____ ----------------------------------------------------------------------------------------------- Total 100 _____2005 8-week summer Organic Chemistry CHE230-001 EXAM 2b page 1/4 Problem 1.HEther (solvent)HOOCF3HO 1. (15 pts.) Draw the product above. Check your work by counting the atoms to make sure you have not done something silly. OHH2B2A 2. Consider the reactions above. a. (10 pts.) Give the reagents and conditions that will accomplish transformation 2A. If you can’t remember this, name process 2A for partial credit. . b. (10 pts.) Suggest reagents and conditions that will accomplish transformation 2B. This is an anti-Markovnikov addition to a double bond. 2A2B2005 8-week summer Organic Chemistry CHE230-001 EXAM 2b page 2/4 3. (30 pts.) Consider the structure below. CCCCCCCCHHHHHHHHHHHHHHHH17Problem 3 a. (5 pts.) With the longest contiguous chain from left to right including carbon atoms 1-7 and with the methyl group possessing carbon atom number 8, which carbon /carbon bond is the strongest? __________ b. (5 pts.) Which carbon /carbon bond is the weakest? __________ c. (10 pts.) Please provide reasons for both your answers. ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ d. (10 pts.) Draw below a product of allylic bromination of the structure above. For example what molecule would you expect if you treated the molecule above with NBS (N-bromosuccinimide) in the presence UV light?2005 8-week summer Organic Chemistry CHE230-001 EXAM 2b page 3/4 4. (15 pts. For all right) Indicate whether a positive or negative enthalpy should be associated with the following processes. a. (4 pts.) Melting cheese to make dip for Nacho chips. b. (4 pts.) Breaking the weak bond in Br2. c. (4 pts.) Water condensing on the surface of a cold beer mug, good thing it is on a coaster! BrHDMFC12H22OProblem 5H2O 5. (10 pts.) Consider the reaction above. Draw two SN1 products of the reaction above. The formula of these two products is provided. DMF is a solvent that can dissolve water and the reactant. CHCl3, NaOHH2OC12H14Cl2Problem 6 6. (10 pts.) Predict the product above. Note: the formula is given; a carbene is involved; there are also stereochemical issues to show in your
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