3. An alkene can be converted into an ether in the three mechanistic steps shown below. Complete this
mechanism by:
• Draw curved arrows to indicate the flow of electrons for each step. Lone pairs are omitted for clarity but
be sure to include lone pairs on atoms that are involved in bond formation/breaking.
• Draw the reaction intermediates in the appropriate boxes. Include all nonzero formal charges.
• Classify each step of the mechanism using the boxes below each arrow as one of the following: acid-
base proton transfer (AB), nucleophilic attack (NA), elimination (E), or rearrangement (R).
H
+ H-OMe
+ MeOH
+ MeOH
H
+ H-OMe
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