3. (25 pts.) As an extension of #2, consider tropolone (1 below). Tropolone is a compound...

 

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3. (25 pts.) As an extension of #2, 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. tropolone 1 O : path 1 H-B: path 2 2 3 + H-B : a. Fill in any missing nonbonding electron pairs, then use curved-arrow formalism to illustrate the "electron flow" of each path. b. Draw all significant resonance contributors of anion 2 that show the delocalization of the negative 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). c. 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). 3. (25 pts.) As an extension of #2, 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. tropolone 1 O : path 1 H-B: path 2 2 3 + H-B : a. Fill in any missing nonbonding electron pairs, then use curved-arrow formalism to illustrate the "electron flow" of each path. b. Draw all significant resonance contributors of anion 2 that show the delocalization of the negative 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). c. 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).

Answer rating: 100% (QA)

F H c 0 3 Rill in any missing nonbonding election pair The... View the full answer