Making Ethers - Acid-Catalyzed Alkoxylation Practice Problems

One way to synthesize ethers is to use alcohols instead of water as the nucleophiles in the acid-catalyzed hydration. Suggest a mechanism for the conversion of the following alkene into the corresponding ether under the given conditions.

Determine the synthesis reaction of the following compound using an alkene as the starting substrate and any other substrate and/or reagent needed. 

Identify the major product formed in the reaction given below. 

Draw a plausible mechanism for the reaction given below.

For the given reaction, the rate-determining step is the _______.

The given compound can be synthesized using an alkene. Determine the synthesis of the following:

Suggest a plausible mechanism for the reaction given below.

What are the electrophile and the nucleophile in the first step of the reaction mechanism?

What are the electrophile and the nucleophile in the second step of the reaction mechanism?

Draw a mechanism involving specific-acid catalysis for the given reaction.

What is the possible mechanism of the following reaction if general-acid catalysis is used?

Show how to accomplish each of the following synthetic conversions.
(i) 2-methyl-but-1-ene → 2-ethyl-2-methyloxirane
(ii) 2-methyl-1-phenylpropan-1-ol → 2,2-dimethyl-3-phenyloxirane
(iii) 5-bromopent-1-ene → tetrahydropyran

Show how to synthesize each ether shown below using simple alcohol as the starting material.
(i) 1-methoxypropane
(ii) 2-methoxy-2-methylpropane
(iii) benzyl cyclohexyl ether

Show how each of the following compounds can be synthesized from but-1-ene.
(i) 2-methoxybutane
(ii) 1-ethoxybutane
(iii) 1-methoxybutan-2-ol