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8A-resonance-handout-key - Chem 8A Fall 2008 Sample...

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Chem 8A, Fall 2008 Sample Questions about delocalized electrons and resonance - ANSWER KEY 1. Indicate which of the following compounds has a nitrogen atom with delocalized electrons? A: follows all guidelines B: violates ii : 2 formal charges C: violates ii & iii : 2 formal charges; negative charge on C D: violates i & ii : only 6 electrons on C; 2 formal charges E: violates i, ii & iv : only 6 electrons on C; 2 formal charges; more charge separation than D Relative Energy: A << B < C << D < E Relative Importance: A (major) > B > C > D > E NH 2 NH 2 CH 3 HN CH 3 NH H 2 C N CH 3 CH 3 CH 3 CH 3 CH=CHNHCH 3 look for the nitrogen directly attached to an sp 2 carbon in a pi-bond this nitrogen is directly attached to a pi-bond, but it does not have a lone pair 2. Each of the following compounds has delocalized electrons. Draw curved arrows showing the movement of electrons between the two resonance structures shown below, and then circle which structure will contribute more to the resonance hybrid, or indicate if they will contribute equally.
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