Skip to main content
Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 77e
Chapter 7, Problem 77e

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:
Chemical reaction diagram showing the dehydration of an alcohol to form an alkene, with sulfuric acid as a catalyst.
(e) How might you shift the equilibrium to the left?

Verified step by step guidance
1
Understand the acid-catalyzed hydration reaction: This reaction involves the addition of water (H₂O) to an alkene in the presence of an acid catalyst, forming an alcohol. The reaction is reversible, meaning the alcohol can revert back to the alkene and water under certain conditions.
Recall Le Chatelier's Principle: This principle states that if a dynamic equilibrium is disturbed by changing the conditions, the system will adjust to counteract the disturbance and restore equilibrium. To shift the equilibrium to the left (favoring the formation of the alkene and water), you need to manipulate the reaction conditions.
Decrease the concentration of water: Since water is a reactant in the forward reaction, reducing its concentration will drive the equilibrium toward the reactants (alkene and water). This can be achieved by removing water from the reaction mixture or using a drying agent.
Increase the concentration of the alcohol: Adding more alcohol to the system will push the equilibrium toward the reactants (alkene and water), as the system tries to counteract the increase in alcohol concentration.
Change the temperature: Acid-catalyzed hydration is typically exothermic in the forward direction. Lowering the temperature can favor the reverse reaction (formation of alkene and water), as the system compensates for the removal of heat.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2m
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Le Chatelier's Principle

Le Chatelier's Principle states that if a dynamic equilibrium is disturbed by changing the conditions, the position of equilibrium shifts to counteract the change. In the context of acid-catalyzed hydration, altering concentration, temperature, or pressure can influence the direction of the reaction, allowing us to predict how to shift the equilibrium to favor either the reactants or products.
Recommended video:
Guided course
04:12
The Electron Configuration

Acid-Catalyzed Hydration

Acid-catalyzed hydration is a reaction where an alkene reacts with water in the presence of an acid to form an alcohol. This process involves the formation of a carbocation intermediate and is reversible, meaning that the products can revert back to the reactants under certain conditions. Understanding this reaction is crucial for manipulating the equilibrium.
Recommended video:
Guided course
06:34
Acid-catalyzed hydration mechanism

Equilibrium Constant (K)

The equilibrium constant (K) quantifies the ratio of the concentrations of products to reactants at equilibrium for a reversible reaction. A change in concentration of either reactants or products will affect the value of K, thus shifting the equilibrium position. By manipulating concentrations, one can effectively shift the equilibrium to the left, favoring the formation of reactants.
Recommended video:
Guided course
02:19
The relationship between equilibrium constant and pKa.
Related Practice
Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

(d) How might you shift the equilibrium to the right?

2
views
Textbook Question

The reaction of (E)-3-chlorohex-3-ene with HCl results in the selective formation of 3,3-dichlorohexane instead of 3,4-dichlorohexane. Explain this result.

9
views
Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH2.

(a) Draw the Lewis structure of CH2.

2
views
Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible.

(a) Propose a mechanism for the formation of an alkene from an alcohol.

1
views
Textbook Question

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH2.

(b) What are the hybridization and shape of the central carbon of CH2?

1
views
Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

(c) Which side of the reaction would be favored by running the reaction at high temperatures?