5) Below we see the acid base reaction of phenol with methanol AND some of the resonance forms of the phenoxide ion that result in phenol having a pKa of 10 for the hydroxyl proton. A) Fill in any missing lone pairs and arrows on the diagram. B) In words, name the different types of arrows in the space provided. Then explain in words what the arrows mean and why we don't use the same type of arrow in the two different situations. C) What type of interaction is holding the sodium ions with the methoxide and the phenoxide? Should the sodium ions be involved in the electron pushing at all? Type of arrow? phenol pKa=10 sodium methoxide phenoxide methanol pKa=15 There are more resonance structures, see PP10 Jan 27th, just drawing a subset. Challenge question: Will be marked on completion only for both the structure of A and the mechanism. Below is a scheme of a proposed reaction. Draw the structure of compound A and suggest a mechanism for its formation. Bonus 1/2 mark for the problem set if correct!: Suggest a mechanism for the conversion of A to the final product