Consider the following ether cleavage reaction in which the two C—O bonds of the ether are labeled with 1 and 2:





Illustrate an arrow-pushing formalism that rationalizes the formation of the two haloalkanes and water. Determine and explain which C―O bond will break first.

• A. The C—O bond labeled with 1 will break first since it will form the less stable carbocation.
• B. The C—O bond labeled with 1 will break first since it will form the more stable carbocation.
• C. The C—O bond labeled with 2 will break first since it will form the less stable carbocation.
• D. The C—O bond labeled with 2 will break first since it will form the more stable carbocation.

Answer: (B)