8A-resonance-handout-key

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

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Unformatted text preview: 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...
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