Ht1-05an - Answers to Hour Examination #1, Chemistry...

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Answers to Hour Examination #1, Chemistry 302X-302A, 2005 1a X O O O Y Cope Moves a double bond out of conjugation - not favorable. In addition, one double bond is less substituted, and hence, less stable. Diels-Alder O O O Moves double bond into the three-ring - unfavorable strain 1b COOCH 3 COOCH 3 COOCH 3 COOCH 3 D-A H 3 C H 3 C H H COOCH 3 COOCH 3 H 3 C H 3 C H 3 C H 3 C H H + Cope cyclobutene- butadiene reverse D-A Con-R Z unstable - and can't be Z - too few vinyl hydrogens
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2. OH SO 2 OH NH 2 HNO 3 H 2 SO 4 H 2 O OH SO 2 OH NO 2 NO 2 HNO 3 H 2 SO 4 OH NH 2 NH 2 OH SO 2 OH HONO HCl H 2 SO 4 N 2 + OH H 2 O H 2 Pd/C H 2 Pd/C heat
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3. Boron has an empty 2 p orbital, so borepin is isoelectronic with the tropylium ion. B R There are six pi electrons (two from each of three double bonds) in a set of fully-filled bonding MO’s. There are no electrons in nonbonding or antibonding orbitals. A Frost circle tells the tale: Furan vs. benzene: Look at the electronic occupancy when the polygons are properly inscribed vertex down. The four electrons in the HOMOs are lower in benzene than in furan.
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4a. Substitution at two positions (
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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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Ht1-05an - Answers to Hour Examination #1, Chemistry...

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