consider-the-following-ether-cleavage-reaction-in-which-the-two-c-o-bonds-of-the

Question

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

Ether cleavage reaction showing C—O bonds labeled 1 and 2, producing haloalkanes and water.

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.

Accepted Answer

The C—O bond labeled with 1 will break first since it will form the more stable carbocation.

Answer

The C—O bond labeled with 1 will break first since it will form the less stable carbocation.

Answer

The C—O bond labeled with 2 will break first since it will form the less stable carbocation.

Answer

The C—O bond labeled with 2 will break first since it will form the more stable carbocation.

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