CHEM 240: Survey of Organic Chemistry at North Dakota State University Midterm Exam 02 - Tue, 23 Sep 2014!! Name:! KEY!

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1 CEM 240: Survey of rganic Chemistry at orth Dakota State University Midterm Exam 02 - Tue, 23 Sep 2014!! ame:! KEY! Please read through each question carefully and answer in the spaces provided. A good strategy is to go through the test and answer all the questions you can do easily. Then go back and tackle the more difficult problems. Please make sure your structures are drawn clearly and indicate any necessary stereochemistry with bold or dashed bonds. inally, think about what you know. Common sense and reason can often help you out. You may use the blank pages of your test for scratch paper. Problem 1 8 pts Problem 7 8 pts Problem 2 10 pts Problem 8 6 pts Problem 3 9 pts Problem 9 14 pts Problem 4 15 pts Problem 5 12 pts BUS 5 pts Problem 6 18 pts TTAL 100 pts Chem 240 Midterm Exam 02! page 1! fall 2014

2 1. Identify the relationship between the following pairs of molecules as Identical, Constitutional Isomers, Stereoisomers or Resonance orms. (check the appropriate box) (8 pts) identical constitutional isomers stereoisomers resonance forms a) b) c) d) 2. Circle all of the following molecules that are aromatic. (10 pts) C 3 3. Segments for three different polymers are show below. or each polymer, draw the structure of the alkene starting material (the monomer) that was used to prepare those polymers. (9 pts) n n n 2 C C 2 alkene starting monomer alkene starting monomer alkene starting monomer Chem 240 Midterm Exam 02! page 2! fall 2014

3 4. As a new manager in a pharmaceutical company, you have been tasked with preparing m-nitrobenzoic acid for use in making a new cancer drug. Your associates brought the following synthetic plan to you for evaluation. Given your vast organic chemistry knowledge, you immediately see that the proposed synthesis will not provide the correct product. iefly explain why the synthesis will not work. In the empty boxes below, provide a synthetic sequence (include reagents over the arrows and intermediate structures along the way) that will be successful to provide m-nitrobenzoic acid. (15 pts) C 3 3 Al C 3 2 C 3 2 C 3 2 S 4 KMn 4 briefly explain what is wrong with the synthetic sequence above Methyl is an o-,p-director. Thus, in the second step, the nitro group will not end up meta to the methyl. provide a synthesis sequence that would give the final product There are two ways this can be done: C 3 KMn Al 4 3 C3 C 3 2 S 4 2 C 3 2 S 4 2 C 3 Al 3 2 C 3 KMn 4 2 C 5. Indicate whether the following statements are True or alse. (12 pts) T T The rate of electrophilic aromatic substitution increases if you place more electron withdrawing groups on the benzene ring. Potassium permanganate will not oxidize toluene (methyl benzene) to benzoic acid. Chlorine on a benzene ring is an ortho-, para-director. Conjugation means that all atoms in a chain are sp 3 -hybridized. Allylic carbocations are more stable than a methyl carbocation. Resonance forms represent a fast equilibrium between multiple compounds. Chem 240 Midterm Exam 02! page 3! fall 2014

4 6. In the electrophilic chlorination of nitrobenzene, the electrophile could add ortho, meta, or para. (a) or the two examples shown below (addition meta and para), fill in all the pi-bonds and formal charges for the carbocation intermediates. (12 pts) complete these structures with pi-bonds and charges 2 2 e e (c) Which of the reaction pathways shown above (meta or para) would be preferred for this example? Provide a brief explanation. (6 pts) The meta addition would be preferred. If the electrophile adds in the para position, the carbocation intermediate ends up adjacent to the electron withdrawing nitro group. 7. Circle all of the following molecules that will react slower than benzene in an electrophilic aromatic substitution reaction. (8 pts) 3 C C The following conjugated diene will react with to generate a carbocation intermediate. The subsequent addition of bromide generates two isomeric products. Provide the structure for the 1,2- and 1,4-products. (6 pts) + 1,2-product 1,4-product Chem 240 Midterm Exam 02! page 4! fall 2014

5 9. Draw the structure for the major organic product for each of the following reactions. Please make sure to show any stereochemistry clearly. (14 pts) 2 a 2 a 2 S 4, 2 gs 4 2 Lindlar's catalyst Chem 240 Midterm Exam 02! page 5! fall 2014

6 BUS: Draw the structure for at least two of the four DA base pairs (Cytosine, Guanine, Adenine, Thymine) (5 pts) 2 Adenine 2 3 C 2 Guanine Thymine Cytosine Chem 240 Midterm Exam 02! page 6! fall 2014

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