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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2:34 minutes

Problem 61k(iv)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O
(k)

Verified step by step guidance

Identify the type of reaction: The reaction involves an alkene reacting with H₂SO₄ (sulfuric acid) and H₂O (water). This is an acid-catalyzed hydration reaction, which adds a water molecule (H and OH) across the double bond of the alkene.

Determine the regioselectivity: Acid-catalyzed hydration follows Markovnikov's rule. This means the hydrogen (H⁺) from H₂SO₄ will add to the carbon of the double bond that has more hydrogens already attached, while the hydroxyl group (OH⁻) will add to the carbon with fewer hydrogens.

Propose the carbocation intermediate: After the protonation of the alkene by H⁺, a carbocation intermediate is formed. Check for the stability of the carbocation. If a more stable carbocation can be formed through rearrangement (e.g., hydride or alkyl shift), this will occur.

Add the hydroxyl group: The OH⁻ group from water will attack the carbocation, forming a new bond. This step completes the addition of water across the double bond.

Finalize the product: Deprotonation of the intermediate (loss of H⁺) will yield the final alcohol product. Ensure the product is consistent with Markovnikov's rule and check for any stereochemistry if applicable.

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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, typically involving alkenes. In the presence of strong acids like H₂SO₄, the double bond of the alkene acts as a nucleophile, attacking the electrophilic hydrogen, leading to the formation of a carbocation intermediate. This step is crucial for predicting the products of reactions involving alkenes.

Carbocation Stability

Carbocation stability is a key concept in understanding the outcomes of reactions involving alkenes. Carbocations are positively charged species that can vary in stability based on their structure; tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects. The stability of the carbocation formed during the electrophilic addition will influence the final product of the reaction.

Hydration Reaction

The hydration reaction refers to the addition of water (H₂O) to an alkene, resulting in the formation of an alcohol. Under acidic conditions, such as with H₂SO₄, the alkene first forms a carbocation, which then reacts with water to yield an alcohol. This process is essential for predicting the products when alkenes react with acids and water, as it determines the final structure of the alcohol formed.

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Related Practice

Textbook Question

Suggest an arrow-pushing mechanism that accounts for the formation of the following products.

(a)

Textbook Question

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄ , H₂O

(a)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(b)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(g)

Textbook Question

Provide a mechanism for the following reactions occurring with rearrangement.

(a)

Textbook Question

Cyclooctene is one of the smaller rings that can form a trans alkene. Would you expect cis-cyclooctene or trans-cyclooctene to react more quickly in an acid-catalyzed hydration reaction?

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

a. 1-methylcyclohexanol

Textbook Question

How can the following compounds be prepared from 3,3-dimethyl-1-butene?

b. 3,3-dimethyl-2-butanol

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