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Chem_358_Prelim_1_S07_solutions

Chem_358_Prelim_1_S07_solutions - 1 Organic Chemistry for...

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1 Organic Chemistry for the Life Sciences Chemistry 358 Spring Semester 2007 Prelim 1 - ANSWERS February 15, 2007 7:30-9:00 PM Name: ANSWERS (Last) (First) (Middle Initial) Do not open until the proctor tells you to do so. There are 7 total pages. Please, count your pages before beginning the exam. Write all answers on the printed side of the exam in the locations indicated. Draw structures clearly. It is your responsibility to convey information unambiguously and not the grader’s responsibility to interpret what you meant. 1. (20) 2. (11) 3. (9) 4. (20) 5. (22) 6. (18) Total (100)
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2 1. (a) (6 Points) Based on your knowledge of the concept of aromaticity, label each of the structures below as aromatic, antiaromatic or nonaromatic. Assume all are planar. N O Aromatic Antiaromatic Aromatic Nonaromatic Antiaromatic Aromatic (b) (8 Points) The 1 H NMR spectra of the annulenes shown below are as follows: D (a) δ 0.00 (4 H) δ 7.60 (10 H) B (b) δ 5.35 (14 H), δ 10.56 (4 H) A (c) δ -4.25 (6 H), δ 8.14-8.67 (10 H) C (d) δ -3.0 (6 H), δ 9.0 (12 H)
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