Exam 14: Ethers, Epoxides, and Thioethers

Diethyl ether is often used as the solvent for reactions with Grignard reagents, but cyclic ethers like ethylene oxide will react with a Grignard reagent to form an alcohol. Why?

What is wrong with the following reaction?

Which of the following compounds would undergo autoxidation most readily?

Draw the correct structure of the expected product of the following reaction.

Provide an acceptable name for the compound shown below.

Lasalocid A (shown below) is an antibacterial agent and a coccidiostat, which is produced by strains of Streptomyces lasaliensis. It is the drug in the feed additives. How many ether functional groups are present in Lasalocid A?

Which of the following is not a true statement?

Which has the higher boiling point, diethyl ether or butan-1-ol? Briefly explain.

What is the complete systematic IUPAC name for the following compound?

Anisole is known by two other names. Give either of them.

Show the reagents necessary to prepare the compound below from cyclohexanone.

What compound is formed when 2,2-dimethyloxirane is treated with ethanol containing a trace of HCl?

Provide the major organic product in the reaction below.

Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis.

Use arrows to show correct electron flow in the mechanism for the reaction below. Include all intermediate structures correctly drawn with formal charges.

Provide the major organic product of the following reactions.

Provide the structure of 3-methoxyfuran.

What is the correct IUPAC name for the following compound?

Provide the major organic product of the following reactions.

Treatment of tetrahydrofuran with excess HBr results in the formation of what major organic product?