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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6:23 minutes

Problem 23c

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?
c.

Verified step by step guidance

Step 1: Analyze the reaction conditions. The reaction involves an alkene (CH3CH═CHCH3) reacting with HCl in the presence of water. This suggests an electrophilic addition mechanism where the alkene reacts with the electrophile (H+) from HCl.

Step 2: Identify the intermediate formed. The alkene undergoes protonation at the double bond, leading to the formation of a carbocation intermediate. The protonation occurs at the more substituted carbon to form the more stable carbocation (Markovnikov addition).

Step 3: Consider the nucleophiles present. In this reaction, there are two potential nucleophiles: Cl⁻ from HCl and H₂O from the aqueous environment. Both can attack the carbocation intermediate.

Step 4: Determine the major product. Water (H₂O) is a stronger nucleophile in the presence of dilute HCl and will preferentially attack the carbocation. This leads to the formation of an alcohol as the major product.

Step 5: Finalize the structure of the major product. After the nucleophilic attack by H₂O, a proton transfer occurs to stabilize the molecule, resulting in the formation of 2-butanol as the major product.

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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 or alkynes. In this process, the double bond of the alkene acts as a nucleophile, attacking the electrophile, leading to the formation of a more stable carbocation intermediate. This mechanism is crucial for understanding how alkenes react with reagents like HCl.

Carbocation Stability

Carbocation stability is a key concept in organic chemistry that determines the outcome of reactions involving carbocations. The stability of a carbocation is influenced by factors such as the degree of substitution (primary, secondary, tertiary) and resonance effects. More stable carbocations are favored in reactions, as they are lower in energy and more likely to form, guiding the direction of nucleophilic attack in electrophilic addition reactions.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of electrophilic addition reactions, as it accounts for the formation of the more stable carbocation intermediate. Understanding this rule is essential for determining the major product in reactions like the one involving HCl and alkenes.

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Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

7. H₂O + H₂SO₄

b. With which reagents do the two alkenes react to form different products?

Textbook Question

What is the product of the reaction of maleate and H₂O when H₂SO4 is used as a catalyst instead of fumarase?

Textbook Question

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed

c. 1-ethylcyclohexene + H₂O + H₂SO₄

Textbook Question

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

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)

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