Problem_Set_1_solutions - Chem 358 Spring 2008 Problem Set...

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Chem 358 Spring 2008 Problem Set #1 (Week #1) - Answers Additional Problems - Answers 1. 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 Principle). Consideration of the possible resonance structures suggests that 1-bromocyclopent-2-ene will react the fastest. Br Br Br Delocalization enforces a planar struture rendering it antiaromatic Here resonance destabilizes No resonace possible 3. See answer to question #2. The compound circled will react the fastest because it will give a very stable aromatic intermediate. O
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Problem_Set_1_solutions - Chem 358 Spring 2008 Problem Set...

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