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0244Pb19-10.cwk (WP)

0244Pb19-10.cwk (WP) - 3 How many electrons are involved 4...

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Problem 19, Chemistry 0244, 2010 To deal with orbital symmetry problems, you MUST have the benchmark 1,3-cyclohexadiene- 1,3,5-hexatriene opening (and closing) utterly under control. So, even though it is in the book in excessive detail, let s do it here too. You should also take a close look at the “How to do orbital symmetry problems” section in Ch 20 - it starts on p 1165. 1. Draw arrow formalisms for the interconversion of cyclohexadiene and 1,3,5-hexatriene. 2. Sketch out the pi molecular orbitals for 1,3,5-hexatriene.
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Unformatted text preview: 3. How many electrons are involved? 4. Identify the HOMO of the open chain partner. 5. What kind of motion is required as the cyclohexatriene opens? Why? 6. What product(s) will be formed from a cis-5,6-disubstituted cyclohexadiene? What product(s) will be formed from the trans counterpart? 7. How will the photochemical reaction differ? The answers are right in the book - Ch. 20, pp 1129ff Compare this answer with that for Problem 34...
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