Final Ans06.cwk - Some Answers to the Final Examination,...

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Some Answers to the Final Examination, Chemistry 301X- 2006 1. (a) HO OH HO OH OH OH A B C D E F H H H H (b) Isomer A is an enol and will isomerize to the ketone form: HO A enol ketone O (c) Problem 15.46
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(d) One Possibility - there are others. one dibromide product OH OH OH Br Br OH Br Br Br Br Br Br (or from bottom) One Possibility for two dibromide products: Br Br Br Br Br Br (or from bottom) OH OH Br OH Br Br Br OH The same two products arise from the other bromonium ion. OH
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(e) One Possibility - there is one other, actually. HO Br Br O Br H O Br X Br HO Br Br Br O also accepted 2. These are not the only possible answers. Other ways may also work. a) IR will do: cis C=C out-of-plane C-H bend: 730-665 cm –1 , trans: 980-960 cm –1 (b) the cis J (0°, ca. 8 Hz) will be larger than the trans J (120°, ca. 2 Hz). (c) Proton-coupled 13 C NMR will show a quartet for ethane and a quintet for methane. (d) many ways: singlet OCH 3 for the first compound at ca. δ 3.6 ppm; singlet CH 3 for the second compound at ca. δ 2.1 ppm. ( e) C=O IR stretch ca. 1720 cm –1 for the six-membered ring; much higher for the four- membered ring. (f) ortho has two different ring hydrogens, para has one and meta has three.
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3. She was clearing thinking that 2 and 3 each had three resonance forms and thus, for an
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This note was uploaded on 03/07/2010 for the course ORGO 1 AND V.0243 taught by Professor Jones during the Spring '10 term at NYU.

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Final Ans06.cwk - Some Answers to the Final Examination,...

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