Exam 1 -09 ans

Exam 1 -09 ans - 1. (a) (b) (d) (c) H H O O N H H (a) Not...

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1. O O N B N B N B H H H H H H N H (a) (b) (c) (d) (a) Not planar - there are eight (not ten) electrons in the pi system. (b) of course! Three points determine a plane. (c) Yes - It is aromatic - see resonance form at the right--->. (d) Yes, nonbonding electrons are in the pi system - aromatic again. N B N B N B H H H H H H + + + (e) nonplanar - not fully conjugated. Were this compound aromatic, the chemical shift of the "alkene" hydrogens would be about 7 ppm. 2. In order to do the Diels-Alder reaction, the s-cis form of the diene must be formed. Thus, cyclopentadiene is the fastest because it is held in that arrangement. The acyclic dienes must put either hydrogens or methyl groups inside. For steric reasons, the fewer methyl groups inside, the better. 1 2 3 4
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3. If you didn’t see this Problem coming, you weren’t paying attention! The low- temperature product must be formed by passing over the lower-energy transition state.
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Spring '10 term at NYU.

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Exam 1 -09 ans - 1. (a) (b) (d) (c) H H O O N H H (a) Not...

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