What are the major products obtained when each of the following ethers is heated with one equivalent of HI?

e.

Propose a mechanism for each of the following reactions:

b.

Explain why HF and HCl cannot be used to cleave ethers in an S_N2 reaction.

What are the major products obtained when the following ether is heated with one equivalent of HI?

When ethyl ether is heated with excess HI for several hours, the only organic product obtained is ethyl iodide. Explain why ethyl alcohol is not obtained as a product.

Predict the products of the following reactions.

(b)

Predict the products of the following reactions.

(c)

Show an arrow-pushing mechanism that rationalizes formation of the two products. Which C―O bond will break first? Why?