Ether Cleavage: Videos & Practice Problems

Give the products of the ether cleavage reaction given below:

What are the products of the ether cleavage reaction given below?

Consider the following ether cleavage reaction in which the two C—O bonds of the ether are labeled with 1 and 2:

Illustrate an arrow-pushing formalism that rationalizes the formation of the two haloalkanes and water. Determine and explain which C―O bond will break first.

Given the ether cleavage reaction below:

Determine the haloalkane and the alcohol that will be produced in this reaction. Consider carefully which carbon-oxygen bond would be broken to form the halide.

What major products are produced when one equivalent of HBr is heated with each of the following ethers?

What major products are produced when one equivalent of HBr is heated with the following ether?

Provide a possible mechanism for the given reaction

True or False. HCl and HF cannot cleave ethers in an S_N2 reaction.

Provide suitable reagents to carry out the following reaction.

Consider the following compound:

When treated with HBr, this compound undergoes cleavage to form 5-bromo-5-methylhexan-1-ol. Write a plausible mechanism for this reaction.

Draw a suitable mechanism for the cleavage of ether shown below.

Show the products expected from the reactions given below.
 
a. methoxycyclopentane + excess of HBr →
b. isopropoxybenzene + excess of HBr →
c. tetrahydrofuran + excess of HI →

Give the equations for the following reactions:

a. Formation of proline benzyl ester
b. It's hydrogenolysis

Show the major products expected from the reactions given below.

a. 2-methoxy-2-methylpropane + HBr (excess), heat →
b. 2-ethoxypropane +  HBr (excess), heat →
c. ethoxyethane + NaOH (conc.), heat →

Provide the reagents to complete the reaction below.

Identify the organic products of the reaction shown below.

Draw the mechanism for the acid-catalyzed hydrolysis reaction given below.

Draw the major products for the reaction of the compound below with 1 equivalent of HBr.

Explain why ethyl isopropyl ether produces both isopropyl bromide and ethyl bromide when it reacts with excess HBr and heat.

Explain briefly why the only organic product obtained is methyl bromide when dimethyl ether is heated with excess HBr.

Propose an arrow-pushing mechanism for the reaction below.

Draw the major products obtained from the given reactions of ethers with 1 eq. of each acid.

The reagent boron tribromide (BBr₃) is used to cleave ethers, producing alcohols and alkyl halide after a subsequent hydrolysis reaction. The general reaction sequence is shown below: 

The mechanism involves a bromide ion attacking the Lewis acid–base adduct of the ether with BBr₃. Suggest a mechanism for the reaction of ethyl propyl ether with BBr₃ and a subsequent hydrolysis reaction to produce propan-1-ol and bromoethane.

Draw the product of the reaction below. Assume that acid is in excess.

1-ethoxy-4-methylbenzene + HBr → 

Provide the product of the reaction below. Assume that acid is in excess.

Identify the product of the reaction shown below:

Give the product of the reaction shown below:

Draw the product of the reaction shown below:

When the following ether undergoes a cleavage reaction using excess HI, it only yields an alcohol and a haloalkane. Considering the mechanism of the ether cleavage reaction, why is iodobenzene not also a product of this reaction?