Chem 8A, Fall 2008Sample Questions about delocalized electrons and resonance - ANSWER KEY1. Indicate which of the following compounds has a nitrogen atom with delocalized electrons?A: follows all guidelinesB: violates ii: 2 formal chargesC: violates ii & iii:2 formal charges; negative charge on CD: violates i & ii:only 6 electrons on C; 2 formal chargesE: violates i, ii & iv:only 6 electrons on C; 2 formal charges; more charge separation than DRelative Energy: A << B < C << D < ERelative Importance: A (major) > B > C > D > ENH2NH2CH3HNCH3NHH2CNCH3CH3CH3CH3CH=CHNHCH3look for the nitrogen directly attached to an sp2carbon in a pi-bondthis nitrogen is directly attached to a pi-bond, but it does not have a lone pair2. 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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