At first glance, this one looks tricky! Look at what is directly attached to each ring and identify it as electron withdrawing (ring deactivating) or electron donating (ring activatin) as the clue...Consider the molecule below, select which of the following site/s will be the most reactive toward electrophilic aromatic substitution.

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This question asks which ring positions will be most reactive toward an electrophilic aromatic substitution (EAS) based on whether the substituents attached to each ring donate or withdraw electrons.

Option a. Sites A and C: These positions are adjacent to or oriented toward substituents that withdraw electron density from the ring, making them less activated toward EAS. Therefore, A and C are not the most reactive.

Option b. Sites D and F: These positions lie in locations where the attached substituents donate electron density to the ring (electron-donating effects). Electron donation increases the ring’s electron density at the ortho/para positions relative to the substituent, making these sites more reactive toward an electrophile during EAS. Additionally, steric factors at these positions are not prohibitive, so D and F are the most activated.

Option c. Site B: If B is on the ring where the substituent withdraws electrons or where resonance effects reduce electron density, its reactivity toward EAS would be diminished compared with the activated positions. This makes B less favored than D or F.

Option d. Site E: Similar to B, E would be influenced by substituent effects that tend to withdraw electron density or otherwise destabilize the arenium intermediate, reducing reactivity relative to the donating sites.

Option e. Sites A, C, D and F: This combines two deactivated positions (A and C) with two activated ones (D and F). Since A and C are not highly reactive, this combination is not the best overall set for maximal EAS reactivity.

Option f. Sites B and E: If B and E are both associated with deactivating substituents or positions with reduced electron density, this pair would be less reactive than the donating sites D and F, and thus not the optimal choice.

In summary, the most reactive sites toward electrophilic aromatic substitution are those that experience electron donation from substituents, increasing the ring’s electron density at the reactive positions. Based on this analysis, Sites D and F are the most activated sites, while the other options involve at least one deactivated or less reactive position. Therefore, the correct choice is Sites D and F.

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