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.

Given the ether cleavage reaction below:

Determine the haloalkane and the alcohol that will be produced in this reaction. Consider carefully which carbon-oxygen bond would be broken to form the halide.

What major products are produced when one equivalent of HBr is heated with the following ether?

Provide a possible mechanism for the given reaction

Show the products expected from the reactions given below.
 
a. methoxycyclopentane + excess of HBr →
b. isopropoxybenzene + excess of HBr →
c. tetrahydrofuran + excess of HI →

Propose an arrow-pushing mechanism for the reaction below.