Problem Set 1-solutions

Problem Set 1-solutions - Chem 358 Spring 2010 Problem...

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Chem 358 Spring 2010 Problem Set #1 (Week #1) - Answers Additional Problems - Answers 1. Here, you just apply the Hückel rule directlysince the molecules are assumed to be planar. planar, cyclic 14 ! e's (n=3) => obeys Hückel's rule => Aromatic planar, cyclic 12 ! e's (n=3) => Does not obey Hückel's rule => Antiaromatic planar, cyclic 8 ! e's (n=2) => Does not obey Hückel's rule => Antiaromatic planar, cyclic 6 ! e's (n=1) => obeys Hückel's rule => Aromatic N H O + O planar, cyclic 8 ! e's (n=2) => Does not obey Hückel's rule => Antiaromatic 2. The reaction that gives the most stable intermediate will be the fastest one (Hammond’s Postulate). Consideration of the possible resonance structures of the expected intermediate carbocation in each reaction suggests that 1-bromocyclopent-2-ene (reaction (c)) will be the fastest. Allylic carbocation is the most stable. Br Br Br Delocalization forces a planar structure rendering it antiaromatic Very unstable carbocation No resonace possible. Allylic carbocation - stabilzed by resonance
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Problem Set 1-solutions - Chem 358 Spring 2010 Problem...

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