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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5:15 minutes

Problem 56b

Textbook Question

Propose mechanisms consistent with the following reactions.
(b)

Verified step by step guidance

Step 1: Analyze the reaction conditions. The presence of H₂SO₄ (sulfuric acid) and H₂O (water) indicates that this is an acid-catalyzed hydration reaction of an alkene. The goal is to add water (H and OH) across the double bond.

Step 2: Protonation of the alkene. The π electrons of the double bond attack a proton (H⁺) from H₂SO₄, forming a carbocation intermediate. The more stable carbocation will form, so consider carbocation rearrangements if applicable.

Step 3: Nucleophilic attack by water. The water molecule acts as a nucleophile and attacks the carbocation, forming an oxonium ion (R-OH₂⁺).

Step 4: Deprotonation of the oxonium ion. A water molecule or another base removes a proton from the oxonium ion, resulting in the formation of the alcohol product.

Step 5: Verify the Markovnikov addition. The OH group is added to the more substituted carbon of the double bond, consistent with Markovnikov's rule, due to the stability of the carbocation intermediate.

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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 context, the double bond of the alkene acts as a nucleophile, attacking the electrophilic sulfuric acid (H2SO4), leading to the formation of a carbocation intermediate. This step is crucial for understanding how the reaction proceeds to form the final product.

Carbocation Stability

Carbocation stability is a key concept in organic reactions, as the stability of the carbocation intermediate significantly influences the reaction pathway. 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 the carbocation formed during the electrophilic addition helps predict the major product of the reaction.

Hydration Reaction

A hydration reaction involves the addition of water (H2O) to a compound, typically resulting in the formation of an alcohol. In the presence of sulfuric acid, water acts as a nucleophile that attacks the carbocation formed during the electrophilic addition, leading to the final product, which is an alcohol in this case. This reaction is essential for converting alkenes into alcohols, showcasing the importance of acid-catalyzed hydration in organic synthesis.

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Related Practice

Textbook Question

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

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

g. H₂O + H₂SO₄

Textbook Question

Propose a mechanism to show how 3,3-dimethylbut-1-ene reacts with dilute aqueous H₂SO₄ to give 2,3-dimethylbutan-2-ol and a small amount of 2,3-dimethylbut-2-ene.

HINT: When predicting products for electrophilic additions, first draw the structure of the carbocation (or other intermediate) that results from electrophilic attack.

Textbook Question

Predict the products of the following hydration reactions.

b. 2-phenylpropene + dilute acid

c. 1-phenylcyclohexene + dilute acid

Textbook Question

Often, compounds can be synthesized by more than one method. Show how this 3° alcohol can be made from the following:

(b) two different alkenes

Textbook Question

When fumarate reacts with D₂O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D₂O?

Textbook Question

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

Textbook Question

d. Is the reaction of 1-butene with HBr regioselective?

e. Is it stereoselective?

f. Is it stereospecific?

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