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

10. Addition Reactions

Acid-Catalyzed Hydration

Organic Chemistry

10. Addition Reactions

Acid-Catalyzed Hydration

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4:45 minutes

Problem 46n

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate. n
(n)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The presence of H⁺ and H₂O indicates an acid-catalyzed hydration reaction, which typically involves the addition of water across a double bond in an alkene.

Step 2: Identify the alkene in the structure. The double bond in the cyclohexene ring is the reactive site for the acid-catalyzed hydration.

Step 3: Protonation of the alkene occurs first. The π electrons of the double bond attack the H⁺, forming a carbocation intermediate. Consider the stability of the carbocation formed; tertiary carbocations are more stable than secondary or primary ones.

Step 4: Water acts as a nucleophile and attacks the carbocation intermediate, leading to the formation of an oxonium ion. This step introduces the hydroxyl group (-OH) to the molecule.

Step 5: Deprotonation of the oxonium ion occurs, resulting in the final alcohol product. Ensure stereochemistry is considered if the reaction creates chiral centers.

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Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, resulting in the formation of a new bond. In the context of alkenes and alkynes, this process often involves the addition of acids or water across the double or triple bonds, leading to the formation of alcohols or other functional groups. Understanding this mechanism is crucial for predicting the products of reactions involving unsaturated hydrocarbons.

Carbocation Stability

Carbocation stability is a key concept in organic reactions, particularly in electrophilic addition mechanisms. Carbocations are positively charged carbon species that can form as intermediates during reactions. Their stability is influenced by factors such as the degree of substitution (primary, secondary, tertiary) and resonance. More stable carbocations are more likely to form and dictate the pathway and products of the reaction, making it essential to consider their formation when predicting reaction outcomes.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving chiral centers, the stereochemistry of the reactants can lead to the formation of specific stereoisomers in the products. When predicting products, it is important to consider stereochemical outcomes, especially in reactions that involve the addition of water or acids, as these can lead to different stereochemical configurations depending on the mechanism and intermediates involved.

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Related Practice

Textbook Question

Each of the following reactions has two nucleophiles that could add to the intermediate formed by the reaction of the alkene with an electrophile. What is the major product of each reaction?

Textbook Question

What is the major product obtained from the acid-catalyzed hydration of each of the following alkenes?

Textbook Question

What is the major product obtained from the acid-catalyzed hydration of each of the following alkenes?

a. CH₃CH₂CH₂CH=CH₂

Textbook Question

When the following compound is hydrated in the presence of acid, the unreacted alkene is found to have retained the deuterium atoms. What does this tell you about the mechanism for hydration?

Textbook Question

Predict the products of the following hydration reactions.

a. 1−methylcyclopentene + dilute acid

Textbook Question

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(a)

Textbook Question

For each of the products you predicted in Assessment 8.39, provide an arrow-pushing mechanism which rationalizes the formation of each product. Make sure your mechanism accounts for all products formed, including stereoisomers and regioisomers, where applicable.

Textbook Question

Provide the alkene that would give the following alcohols under acid-catalyzed hydration conditions.

(a)

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