CH_318N_Lecture8-08_Spring_08

CH_318N_Lecture8-08_Spring_08 - Lecture 8 Aromatics...

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1 Chemistry 318N Lecture 8 February 12, 2008 Aromatics Chemistry 318N First Midterm Exam c When: Wednesday, 2/20 c When: 7-9PM c Where: WEL 1.308 c What: Covers material through this Thursday c Review: 2/18 6:00 PM Lecture Room c Review: 2/19 6:00 PM Painter 3.02 c Practice: Exams will be posted on the web site c Please…bring pencils, an eraser and a calculator only and ……. Do a good job!!!
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2 Chemistry 318N What in the World is Benzene?? c C 6 H 6 discovered by Michael Faraday in 1823 – Synthesized in 1834 from benzoic acid – Remarkable chemical stability – Unsaturation number is very high but…. c Does not add Bromine c Substitution with Br 2 / FeBr 3 c Not oxidized by Permanganate or ozone c No reaction with strong HBr (aq) c No reaction with Hydrogen on Pd. . ?????? Chemistry 318N Addition vs Substitution…a Mystery Addition of Bromine to Cyclohexene + Br Br Br 2 + Br 2 FeBr 3 Br + HBr Substitution of Bromine for Hydrogen in Benzene C 6 H 6 + Br 2 C 6 H 5 Br + HBr C 6 H 10 + Br 2 C 6 H 10 Br 2
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3 Chemistry 318N H 2 C C C C C CH 2 H H Some Alternative Structures for Benzene Chemistry 318N Friedrich August Kekulé (1829-1896)
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4 Chemistry 318N Friedrich August von Kekule had a dream of whirling snakes, and the structure of benzene. He reported the dream in the following words in 1890, in a speech at a dinner commemorating his discovery that reportedly occurred during a “reverie” on a London bus. Again the atoms were gamboling before my eyes. This time the smaller groups kept modestly to the background. My mental eye, rendered more acute by repeated vision of this kind, could not distinguish larger structures, of manifold conformation; long rows, sometimes more closely fitted together; all twining and twisting in snakelike motion. But look!
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This note was uploaded on 04/07/2008 for the course CH 318N taught by Professor Willson during the Spring '08 term at University of Texas at Austin.

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CH_318N_Lecture8-08_Spring_08 - Lecture 8 Aromatics...

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