Problem_Set_1 - (a δ 0.00(4 H δ 7.60(10 H(b δ 5.35(12 H...

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Chem 3580 Spring 2008 Problem Set #1 (Week #1) [Ch 14 : 29b-f, 31-33, 35, 37, 39-42, 45, 46, and 48-50. See Study Guide and Solutions Manual for answers.] Additional Problems 1. 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 H O + O 2. Which of the following compounds will react fastest in an S N 1 solvolysis reaction (RBr + H 2 O —> ROH + HBr) ? Provide reasons for your choice. Br Br Br 3. Which of the following alkyl halides will react the fastest in an S N 1 solvolysis reaction (RBr + H 2 O —> ROH + HBr)? Give reasons for choice. O O O Br Br Br 4. The 1 H NMR spectra of the annulenes shown below are as follows:
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Unformatted text preview: (a) δ 0.00 (4 H) δ 7.60 (10 H) (b) δ 5.35 (12 H), δ 10.56 (4 H) (c) δ-4.25 (6 H), δ 8.14-8.67 (10 H) (d) δ-3.0 (6 H), δ 9.0 (12 H) Match each spectrum with each structure. CH 3 CH 3 A B C D H H H H 5. 3-Chlorocyclopropene, on treatment with AgBF 4 , gives a precipitate of AgCl and a stable solution of a product that shows a single 1 H NMR absorption at δ 11.04. Propose a plausible structure for the product and explain its stability. Cl H 6. (a) Azulene, an isomer of naphthalene, has a large dipole moment ( μ = 1.0 D). Explain. (b) Indole is an aromatic heterocycle that has a benzene ring fused to a pyrrole ring. Draw an orbital picture of indole. N H...
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