5. Draw all reasonable resonance structures of the following molecule. Please remember to add in all electron pairs, when needed.

For the species below draw additional resonance structures (where all atoms have access to an octect of electrons) for species A, B, C, and D. Determine the bond order of the bond from the underlined C to underlined O for the lowest energy structure(s). You may need to evaluate the formal charge of the additional species you draw. These are species in an aprotic solvent, so only electrons may be moved, not hydrogen atoms. For each lettered structure below, input the bond order as an integer (1,2,etc) or improper fraction (4/3, 5/4, etc). A Structure Bond Order A HO: (f) H B B С Which structure A-D has the longest underlined C-O bond? :N=C=0: D D

Draw the resonance structures for the molecule, and rank the structures. (There should be four other structures). Keep in mind the rules for drawing and ranking resonance structures!   ***Note, I have only drawn one. It is difficult for me to figure out what the other three are. Thank you

2) (cont.) In the box below each Lewis drawing, PRINT one of the three following ABBREVIATIONS to characterize that Lewis drawing's relevance to the molecule's ACTUAL structure. i) CRS (Contributing Resonance Structure) ii) RS (Resonance Structure but not a CRS) iii) NRS (Not a Resonance Structure)