12. Alcohols, Ethers, Epoxides and Thiols

Predict the product of the following reactions.

(b)

Suggest a mechanism by which TXB₂ might be formed from TXA₂ in an acid-catalyzed hydrolysis reaction. [The structure has been simplified.]

Predict the product(s) of the following reactions.

(k)

Predict the products of the following reactions. An excess of acid is available in each case.

(d)

Suggest the reagents used to effect the transformations shown.

(c)

Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.

The reaction is thought to involve attack by a bromide ion on the Lewis acid–base adduct of the ether with BBr₃ (a strong Lewis acid). Propose a mechanism for the reaction of butyl methyl ether with BBr₃ to give (after hydrolysis) butan-1-ol and bromomethane.

What is the major product(s) of each of the following reactions?

a.

b.

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

e.

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

Predict the products of the following reactions.

(c)

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. An excess of acid is available in each case.

(c) anisole (methoxybenzene) + HBr

Propose a mechanism for the following reaction.

Propose a mechanism for each of the following reactions:

a.