12. Alcohols, Ethers, Epoxides and Thiols

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

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[SOLVED] Explain why methyl propyl ether forms both methyl iodide and propyl iodide when it is heated with excess 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.

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(••) Suggest the reagents used to effect the transformations shown.

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

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Propose a mechanism for each of the following reactions:

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

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Predict the products of the following reactions.

An excess of acid is available in each case.

(c) <IMAGE of reaction>

Boron tribromide (BBr3) cleaves ethers to give alkyl halides

and alcohols.

R-O-R′ + BBr3 → R-O-BBr2 + R′Br

R-O-BBr2 + 3H2O → ROH + B(OH)3 + 2HBr

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) <IMAGE of reaction>

Predict the product of the following reactions.

(a) <IMAGE>

Predict the product of the following reactions.

(b) <IMAGE>

(••) Predict the product(s) of the following reactions.

(k) <IMAGE>