Draw the resonance contributors for the species/molecules shown in the boxes below. Then, indicate which species (if any) is the MAJOR contributor towards the resonance hybrid (most stable).
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Draw the resonance contributors for the species/molecules shown in the boxes below. Then, indicate which species (if any) is the MAJOR contributor towards the resonance hybrid (most stable).
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- O REPRESENTATIONS OF ORGANIC MOLECULES Ranking resonance structures Rank the resonance structures in each row of the table from major to minor. For example, in the first row, select (major) for the major resonance contributor. If two or more structures in the same row contribute equally, rank them equally by selecting the same number. H. H H. H. H. H. H. H. (Rank) (Rank) (Rank) H. H. H. H. H. H. H. (Rank) (Rank) :o: Rank) (Rank) 74°F DELL F5 F6 F7 F8 F9 F10 F11 PrtScr F12 24Follow the curved arrows and draw a second resonance structure for each species. a. CH,-NEN: b. CH3-C-CH CHe NH2 C. d. CHa. Draw as many possible resonance structures of the molecule, (show the direction of electron transfer using curved arrows) b. label the major contributor in the resonance (if any) Draw the resonance hybrid. С. ОН CH3 Molecule A
- Model 3: Stability of Resonance Forms Not all resonance forms have the same energy; some forms may be more stable than others. The major resonance contributor is determined by the following factors (where 1 is more Important and 5 is less important): 1. complete octet 2. as many bonds as possible 3. no charge on individual atoms 4. if charges exist, then negative charge resides on more electronegative atom, or positive charge resides on less electronegative atom 5. if charges exist, then small charge separation between charged atoms :0: R 7 R H + Questions: 8. For the resonance forms shown in Model 3: (a) (b) (c) (d) (e) 8 H H gh H H R Circle any atoms in Model 3 that do not have complete octets. Indicate the total number of bonds for each structure shown in Model 3. 9 Which structure has no charges on any individual atoms? If charges exist, which atom is most likely to hold the negative charge? (C, H, or O) Based on the rules in Model 3, which structure would be the major contributor?…Draw all reasonable resonance structures for each species. a. O3 c. Ng e. g. :O: :O: b. NO, (a central N atom) d. CH3-C-CH-C-CH, 1. CH2=CH-CH-CH=CH23. Provide at least one significant alternative resonance form for each molecule below. Generate a total of six correct structures to receive credit for this question. Provide curved arrows on the given structure to show how it relates to the first structure you draw in each case. An example is shown below in blue. A. R2N° C. R2N. E. B. D.
- 4. Draw two plausible (equally or more contributing) resonance structures of the following compounds or reactive intermediates. Use arrow pushing to show the interconversion of resonance structures. a. b. C. d. H H-O-H N H N HO: B :0 :0: H H 0: 1 11.) Draw other reasonable resonance forms for the following structures. Circle the best resonance form for each structure. 4. a. b. NH₂IX. a. b. Draw all possible resonance structures for the species below. Show the movement of electrons using arrows. H₂C :O: H₂C=CH CH₂ CH=CH- + CH -CH3
- 2. Each resonance structure of a given molecule contributes to the resonance hybrid. The more stable the resonance structure, the more that resonance structure contributes to the resonance hybrid. For the following resonance structures, a. Circle the resonance structure that contributes most to the resonance hybrid. b. Explain your choice for a in complete sentences. c. Draw the resonance hybrid. d. Add curved arrows to indicate the flow of electrons in each structure except the D. H A Q Search B hyji C D2. Draw a Lewis structure for each molecule or ion below. Draw any resonance structures. Determine the form al charges on atoms in each of your resonance structures. Based on this, determine which resonance structure(s) are most im portant. Circle the most important contributor(s) to the resonance hybrid. If they are all equivalent, circle them all. a. NO, b. COFCId. b. e o C. a. O 6. Draw at least 3 additional (l.e., in addition to the structure provided) valid resonance (major contributors only) forms of the following ions: Ⓒ