Consider the structure of anisole (also called methoxybenzene). In the next chapter, we will discuss whether a methoxy group is electron donating or electron withdrawing. We will see that there is a competition between two factors. Specifically, we will see that the methoxy group is electron withdrawing because of induction, but it is electron donating because of resonance.

a) Draw the resonance structures of anisole.

b) Whenever resonance and induction compete with each other, resonance is generally the dominant factor. Using this information, predict the regiochemical outcome of a Birch reduction of anisole.