Ease Into Prep with a DAT^® Question of the Day

The correct answer is E.

Stop: This question is about resonance structures.

Think: Resonance structures exist when bonds shift between similarly hybridized atoms (e.g. sp²) within the same molecule. These structures must not change the charge of the molecule (e.g., if the molecule has a net 1+ charge, then all resonance structures must have a net 1+ charge). So long as these rules are met, a structure is considered a valid resonance structure.

Predict: All carbons in the molecule are sp² hybridized. The oxygen is sp³ hybridized in the original image, but its position on the phenyl ring allows it to also become sp² hybridized and undergo resonance stabilization with the rest of the ring. This allows for the resonance structures shown below:

Match: Answer choice (E) agrees with that reasoning.