Exam 14: Ethers, Epoxides, and Thioethers

When hexan-1-ol is treated with conc. H₂SO₄ at moderate temperatures, ________ is formed via a(n) ________ mechanism.

Propose a structure for the ether of formula C₄H₁₀O with the following ¹H NMR signals: δ 1.20 (triplet, 6H), δ 3.45 (quartet, 4H) (ppm).

Give two properties of ethers which allow them to be commonly used as solvents in organic reactions.

Which of the following reactions or series of reactions will lead to formation of trans-2-methoxycyclohexanol?

Show how propyl cyclopentyl ether can be prepared starting with cyclopentene and using an alkoxymercuration-demercuration route.

Provide the major organic product of the following.

The presence of what product of the autooxidation of ethers makes the distillation of ethers dangerous?

Provide the major organic product in the reaction below.

Provide the necessary reagents to complete the following reaction.

Some ethers can be prepared by heating the appropriate alcohol in the presence of sulfuric acid. Can di-sec-butyl ether be prepared from sec-butanol by this route? Explain your answer.

Which of the following is an acceptable way to synthesize t-butyl ethyl ether?

When ethers are stored in the presence of oxygen, what explosive materials can result from autoxidation of the ether?

Provide the sequence of reactions by which propoxycyclohexane can be prepared through a Williamson ether synthesis.

Suggest a reasonable mechanism for the reaction shown below.

Provide an acceptable name for the compound shown below.

Provide the major organic product of the following.

Propose fragmentations to account for the 59, 73, and 107 peaks in the MS of the ether below.

Provide the major organic product in the reaction below.

Provide the major organic product of the following.

What compound is formed when methyloxirane is reacted with ethylmagnesium bromide followed by treatment with aqueous acid?