Making Ethers - Acid-Catalyzed Alkoxylation - Online Tutor, Practice Problems & Exam Prep

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

Which alkene and alcohol reactants can form the ether shown below?

Draw the reaction coordinate diagram of the addition reaction of ethyl alcohol to ethylene that is acid-catalyzed and determine the rate-determining step.

Draw the major products that would form given the reaction conditions below.

Prepare the following compound from an alkene.

Synthesize the given compound from an alkene.

Draw the products that could be formed from the reaction of cis-3-hexene and trans-3-hexene with CH₃CH₂OH in the presence of H₂SO₄. Show stereochemistry.

Will cis-3-hexene form different products from those of trans-3-hexene?