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4. (16 pts.) As an extension of #1, consider tropolone ( 1 below). Tropolone is a compound that can act as an acid by donating

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4. (16 pts.) As an extension of \#1, consider tropolone ( 1 below). Tropolone is a compound that can act as an acid by donating a proton (H+)via attack by generic base B(path 1) to form anion 2. Tropolone also can act as a base by accepting a proton (from H-B; path 2) to form cation 3 . a. Fill in any missing nonbonding electron pairs (in the above scheme), then use curvedarrow formalism to illustrate the "electron flow" of each path. b. Draw all significant resonance contributors of cation 3 that show the delocalization of the positive charge. (There are five, including the original representation.) Be sure to use curved arrows to interconvert the contributors. Also, be sure to encircle any formal charges(s)

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