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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4:02 minutes

Problem 6a

Textbook Question

Predict the products of the following hydration reactions.
a. 1−methylcyclopentene + dilute acid

Verified step by step guidance

Step 1: Recognize that the reaction involves the hydration of an alkene using dilute acid. This is an electrophilic addition reaction where water adds across the double bond.

Step 2: Identify the alkene in the structure. The double bond is located within the cyclopentene ring, and the substituent is a methyl group attached to the ring.

Step 3: Understand the mechanism. The dilute acid (H⁺) protonates the double bond, forming a carbocation intermediate. The stability of the carbocation is crucial, and rearrangements may occur to form the most stable carbocation.

Step 4: Predict the regioselectivity of the addition. According to Markovnikov's rule, the hydroxyl group (−OH) will add to the more substituted carbon of the double bond, while the hydrogen (H⁺) will add to the less substituted carbon.

Step 5: Draw the product. The final product will be an alcohol where the −OH group is attached to the more substituted carbon of the original double bond, resulting in 1-methylcyclopentanol.

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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 case of hydration reactions, the alkene acts as a nucleophile, attacking an electrophilic species, such as a proton from an acid, leading to the formation of a carbocation intermediate.

Carbocation Stability

Carbocation stability is crucial in predicting the products of reactions involving alkenes. The stability of a carbocation is influenced by its degree (primary, secondary, tertiary) and the presence of electron-donating groups. More stable carbocations are favored during reactions, guiding the formation of the final product in hydration reactions.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of hydration reactions, indicating that the hydroxyl group will preferentially add to the more substituted carbon of the alkene.

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Related Practice

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

(n)

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)

Textbook Question

The hydration of three C₅H₁₀ alkene isomers can give 2-methylbutan-2-ol. Draw them.

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Predict the products of the following hydration reactions. a. 1−methylcyclopentene + dilute acid

Key Concepts

Electrophilic Addition

Carbocation Stability

Markovnikov's Rule

Watch next

Predict the products of the following hydration reactions.
a. 1−methylcyclopentene + dilute acid