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 2010 Problem Set #1 (Week #1) [Ch 14 : 31-33, 35-37, 40-43a, 45, 46, and 48-49. 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. Give reasons for your answers. (If possible a ring will be nonplanar to avoid being antiaromatic.) N H O + O 2. Which of the following reactions would you expect to give the highest reaction rate ? Provide reasons for your choice. Br Br Br H 2 O ! OH H 2 O ! OH H 2 O ! OH (a) (b) (c) H 2 O ! Br OH (d) 3. 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 4. 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 5. Write the important resonance structures for Azulene. This is an isomer of naphthalene and has a large dipole moment ( μ = 1.0 D). Rationalize the high dipole moment....
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