Acid-Catalyzed Hydration Practice Problems

Determine the identity of products obtained in the hydration reaction shown below.

What is the product formed when the given alkene reacts with H ₂O and H₂SO₄?

Consider the given arrow-pushing mechanism for the reaction of an alkene with H ₂O and H₂SO₄.

Does the mechanism show the formation of all the possible products, as well as stereoisomers and regioisomers, if applicable?

Provide the alkene that, under conditions of acid-catalyzed hydration, would yield the following alcohol.

The acid-catalyzed hydration of three isomers of C₉H₁₈, an alkene, produces 1,3,3-trimethylcyclohexan-1-ol. Draw the isomers.

If the synthesis of an alkene from an alcohol by acid-catalyzed dehydration is a reversible mechanism, what is the possible mechanism for the synthesis of an alcohol from an alkene shown below?

Provide a reagent to perform the following reaction.

What are the products of the reaction of the alkene molecule shown below with H ₂SO₄ and H₂O?

What are the products formed from the reaction of the alkene molecule given below with H  ₂O?

Draw the products formed from the reaction of the given compound with NaOH and H  ₂O.

Determine the product(s) formed when the following molecule reacts with H ₂SO₄ and H₂O.

What are the products formed when the alkene shown below reacts with H  ₂SO₄ and H₂O?

Determine the product(s) formed when the following molecule reacts with H ₂SO₄ and H₂O.

What are the products formed when the alkene given below reacts with H  ₂SO₄ and H₂O?

Provide the reaction sequence of how 2,2-dimethylcyclohexanol can be prepared from 3,3-dimethylcyclohex-1-ene.

Determine the major product formed in the acid-catalyzed hydration of 4-methylpent-2-ene.

Determine the major product formed in the acid-catalyzed hydration of the given compound.

In the reaction illustrated below, the intermediate generated after the electrophilic addition to the alkene can react with two nucleophiles present in the solution. Predict the major product in this reaction. 

Write the products formed in the reaction given below. Indicate which stereoisomers are formed, if possible.

Determine the products that were formed in the reaction shown below. If possible, indicate the stereochemistry of the products. 

Determine the expected product of the reaction of (E)-but-2-enoic acid and H₂O in presence of H₂SO₄ as a catalyst.

I. Write the products formed in the reaction of (E)-pent-2-ene and (Z)-pent-2-ene with H₂O in the presence of H₂SO₄. Indicate which stereoisomers are formed, if possible.

II. State whether the two alkenes form the same or different products. 

The unreacted alkene in the following compound retained the deuterium atoms after it was hydrated in the presence of acid. Which of the following claims regarding the mechanism for the hydration process is/are true?

Given below are the second-order rate constants (in units of M^-1s^-1) for the acid-catalyzed hydration of the four alkenes at 25°C. Identify the correct order of the rates of hydration starting with the alkene that reacts the fastest.

Predict the identity of the major product of the following reaction and provide the structure of its intermediate.

Devise an approach for the synthesis of 1-methylcyclopentanol from methylenecyclopentane and any other required reagents.

Draw the mechanism of the reaction below. Take note of rearrangements.

Which between the two forms of cyclononene is expected to react at a higher rate in acid-catalyzed hydration?

The mechanism of the acid-catalyzed hydration of an alkene to make an alcohol is shown below. Sketch the mechanism of the reverse reaction.

Is the following acid-catalyzed hydration reaction expected to have an equal or unequal yield of stereoisomers?

In the reaction between DDP and IPP, which acts as the electrophile? What is the reason that makes it a better electrophile? [Hint: Consider the carbocation formed by each.]

Propose a reaction mechanism when tetraprenol is synthesized from IPP and DDP.

Draw the structure of the compound that is the product of the reaction of the given alkene with H₂O and H₂SO₄.

The diol shown in the reaction is not produced by the hydration of the given octahydronaphthalen-2-ol. What is the possible reaction mechanism to produce the actual product?

Consider the reversible acid-catalyzed hydration of the alkene shown below: 

Which of the following would shift the equilibrium to the right?

Which compounds are produced when the alkene reacts with H₂O and H₂SO₄?

The acid-catalyzed hydration of an alkene to an alcohol is a reversible reaction. 

Is the mechanism shown below correct for the forward reaction? Why?

The pK_a values of 2-oxopentanedioic acid are 2.47 and 4.68. It has been inferred that the amount of hydrate present in an aqueous solution of 2-oxopentanedioic acid will decrease with increasing pH until around pH 6 and then remain relatively constant beyond that. Why is this so?

Provide a reaction to form the compound below using an alkene as the starting material.

Provide a reaction for synthesizing the compound below using an alkene as the starting material.

Provide the alkene and other reagents needed to synthesize the compound below.

Give the stereoisomers produced by the reaction shown below.

Consider the acid-catalyzed hydration reaction shown below, 

(i) Determine the number of transition states

(ii) Determine the number of intermediates

(iii) Determine the step in the forward direction with the smallest rate constant.

What is the mechanism for the reaction shown below?

Identify the compound that is more rapidly hydrated.

Propose a synthesis of the given alcohol starting with an alkene.

Determine the major product formed in the reaction of 3-ethylpent-2-ene with H₂O and H₂SO₄.

Draw the mechanism that demonstrates the reaction of 3,3-dimethylhex-1-ene with a diluted aqueous H₂SO₄, which produces 2,3-dimethylhexan-3-ol (major product) and 2,3-dimethylhex-2-ene (minor product).

Provide the plausible mechanism for the given reaction.

What are the resulting products of acid-catalyzed hydration reactions of (i) 2-(prop-1-en-2-yl)naphthalene and (ii) cyclopent-1-en-1-ylbenzene?

Many molecules can be synthesized in more than one way. Propose the synthesis of the given tertiary (3°) alcohol from two different alkenes.

Suppose that W catalyzes the reaction of X with D₂O to form only isomer Y. What does W catalyze, a syn- or an anti-addition of D₂O?

The following acid-catalyzed reaction transforms grandisol into a bicyclic alcohol. Determine the mechanism for the reaction described.

Consider the following conversion of compound A to compound B:

What is the mechanism for the reverse reaction, which is the acid-catalyzed conversion of compound B to compound A? What makes this mechanism correct?

Identify the correct statement for the acid-catalyzed hydration reaction of 1-pentene.