12. Alcohols, Ethers, Epoxides and Thiols

Predict the products of the following reactions.

(a) sec-butyl isopropyl ether + concd. HBr, heat

(b) 2-ethoxy-2-methylpentane + concd. HBr, heat

(c) di-n-butyl ether + hot concd. NaOH

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

(a) ethoxycyclohexane + HBr

(b) tetrahydropyran + HI

(c) anisole (methoxybenzene) + HBr

Propose a mechanism for the following reaction.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Suggest the reagents used to effect the transformations shown.

(c)

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

Propose a mechanism for each of the following reactions:

a.

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

a.

b.

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

(c) anisole (methoxybenzene) + HBr

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.

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

(d)

Predict the product of the following reactions.

(a)

Predict the product of the following reactions.

(b)

Predict the product(s) of the following reactions.

(k)