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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Problem 39b

Textbook Question

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

Verified step by step guidance

Step 1: Identify the functional group in the given molecule. The structure contains an alkene functional group (a double bond) in a cyclic compound.

Step 2: Understand the reaction conditions. The reaction involves H2SO4 (sulfuric acid) and H2O (water), which typically leads to an acid-catalyzed hydration of the alkene. This reaction follows Markovnikov's rule.

Step 3: Apply Markovnikov's rule. In acid-catalyzed hydration, the hydrogen atom from H2O will add to the carbon of the double bond with more hydrogens (less substituted), and the hydroxyl group (-OH) will add to the carbon with fewer hydrogens (more substituted).

Step 4: Consider carbocation stability. During the reaction, a carbocation intermediate is formed. The stability of the carbocation is crucial, and rearrangements may occur to form a more stable carbocation (e.g., tertiary carbocation).

Step 5: Draw the expected product. After the addition of H2O, the double bond is replaced by a single bond, and an -OH group is added to the more substituted carbon of the original double bond, resulting in an alcohol 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. 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 understanding how alkenes react with acids and water.

Carbocation Stability

Carbocation stability is a key concept in organic reactions, as the stability of the carbocation intermediate significantly influences the reaction pathway and product formation. Carbocations can be classified as primary, secondary, or tertiary, with tertiary carbocations being the most stable due to hyperconjugation and inductive effects. Understanding the stability of these intermediates helps predict the major product of the reaction.

Hydration Reaction

The hydration reaction involves the addition of water (H₂O) to an alkene, resulting in the formation of an alcohol. In the context of the reaction with H₂SO₄, the acid first protonates the alkene to form a carbocation, which is then attacked by water. This process is essential for converting alkenes into alcohols and is a common method for synthesizing alcohols in organic chemistry.

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Related Practice

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(d) How might you shift the equilibrium to the right?

Textbook Question

When combining isoprene equivalents, IPP is never the electrophile. Why might this be? What is special about DPP that allows it to function better as an electrophile? [Draw the carbocation that each becomes.]

Textbook Question

Suggest a mechanism for the synthesis of farnesol beginning with IPP and DPP.

Open Question

Draw a mechanism for the acid-catalyzed, nonenzymatic conversion of DPP to IPP. How do you know your mechanism is correct?

Textbook Question

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(b) Without looking back, how do you know this mechanism is correct?

Textbook Question

The pK_a values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.

b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials?

Textbook Question

How could the following compounds be prepared using an alkene as one of the starting materials?

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

Key Concepts

Electrophilic Addition

Carbocation Stability

Hydration Reaction

Watch next

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