Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

9. Alkenes and Alkynes

Dehydration Reaction

Organic Chemistry

9. Alkenes and Alkynes

Dehydration Reaction

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4:29 minutes

Problem 77c

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?

Verified step by step guidance

Step 1: Recognize that the reaction shown is an equilibrium between an alcohol and an alkene, with water as a byproduct. The reaction is acid-catalyzed using H2SO4.

Step 2: Recall Le Chatelier's Principle, which states that a system at equilibrium will shift to counteract changes in conditions. Temperature is one such condition that can influence the equilibrium.

Step 3: Understand that this reaction involves a dehydration process (removal of water) to form the alkene. Dehydration reactions are typically endothermic, meaning they absorb heat.

Step 4: Since the reaction is endothermic, increasing the temperature will favor the formation of products (alkene and water) because higher temperatures drive endothermic reactions forward.

Step 5: Conclude that running the reaction at high temperatures will favor the side of the reaction that produces the alkene and water, shifting the equilibrium toward the products.

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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, increasing temperature will favor the endothermic direction of the reaction, which can help predict the favored side of the reaction under high-temperature conditions.

Endothermic vs. Exothermic Reactions

Reactions can be classified as endothermic or exothermic based on their heat exchange with the surroundings. Endothermic reactions absorb heat, while exothermic reactions release heat. Understanding which side of the hydration reaction is endothermic or exothermic is crucial for predicting how temperature changes will affect the equilibrium position.

Equilibrium Constant (K)

The equilibrium constant (K) quantifies the ratio of the concentrations of products to reactants at equilibrium for a reversible reaction. Changes in temperature can alter the value of K, influencing the position of equilibrium. A higher temperature may shift the equilibrium towards the side with a higher K value, indicating a preference for products or reactants depending on the reaction's thermodynamics.

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Predict the product of the following pinacol rearrangements.

(c)

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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'

(a)

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What product is obtained when the following vicinal diol is heated in an acidic solution?

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What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

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Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

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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?

Key Concepts

Le Chatelier's Principle

Endothermic vs. Exothermic Reactions

Equilibrium Constant (K)

Watch next

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?