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Recitation__2_Sept_2_ANSWERS - Organic Recitation#2...

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Organic Recitation #2 September 2, 2007 Chemistry 357 - Qatar Organic Chemistry for the Life Sciences Recitation Exercises – ANSWER KEY 1. Using curved-arrow notation, show how electrons in the left structure move to produce the second resonance structure. For each example, provide the resonance hybrid that reflects the overall bonding picture including partial charges where necessary. In each example in, the second resonance structure is a MORE IMPORTANT CONTRIBUTOR to the resonance hybrid structure and thus, the properties of the species. Explain the reason(s) why? a) H C C H O C H H resonance hybrid H C C H O C H H H C C H O C H H ! + ! - Explanation: There are two reasons that explain why the right resonance structure is more important. First and most importantly, the structure on the left contains a carbon without a filled octet. This is very destabilizing. Second, recall that “No molecule or atom in its right mind wants to be charged”…. Dr. P . The first resonance structure (left) has the destabilizing separation of charge . Moving the electrons to generate the second resonance structure results in a molecule without any formal charges. Therefore, the structure on the right will be a stronger contributor to the chemistry of the hybrid.
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