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

Previous problemNext problem

3:38 minutes

Problem 14e

Textbook Question

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

Verified step by step guidance

Analyze the target compound: The structure provided is 2-methyl-2-butanol, which is a tertiary alcohol. This indicates that the hydroxyl group (-OH) is attached to a carbon atom that is bonded to three other carbon atoms.

Identify the alkene precursor: To synthesize 2-methyl-2-butanol, the alkene precursor should be 2-methyl-2-butene. This is because the double bond in the alkene will allow for the addition of the hydroxyl group at the tertiary carbon.

Choose the reaction mechanism: The preparation of a tertiary alcohol from an alkene typically involves an acid-catalyzed hydration reaction. This reaction uses water (H₂O) and an acid catalyst, such as sulfuric acid (H₂SO₄), to add a hydroxyl group to the more substituted carbon of the double bond (Markovnikov addition).

Outline the reaction conditions: Mix 2-methyl-2-butene with water in the presence of a strong acid catalyst (e.g., H₂SO₄). The acid will protonate the alkene, forming a carbocation intermediate at the tertiary carbon. Water will then attack the carbocation, leading to the formation of 2-methyl-2-butanol after deprotonation.

Verify the product: Ensure that the reaction follows Markovnikov's rule, resulting in the hydroxyl group attaching to the tertiary carbon. The final product should match the structure of 2-methyl-2-butanol.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition, polymerization, and oxidation. Understanding the types of reactions that alkenes can participate in is crucial for determining how to synthesize other compounds from them.

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of electrophiles to the electron-rich double bond of alkenes. This process typically results in the formation of more saturated products. Common electrophiles include halogens, hydrogen halides, and water, and the regioselectivity of these reactions can lead to different products based on the stability of the resulting carbocation intermediates.

Synthesis Strategies

Synthesis strategies in organic chemistry involve planning the steps needed to convert starting materials into desired products. This includes selecting appropriate reactions, understanding reaction conditions, and predicting the outcomes. When preparing compounds from alkenes, it is essential to consider the functional groups present in the target compounds and how they can be introduced through various transformations.

Watch next

Master General properties of acid-catalyzed hydration. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(b)

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

Using any alkene and any other reagents, how would you prepare the following compounds?

Textbook Question

Which compound is hydrated more rapidly?

Textbook Question

Propose a mechanism for the following reaction:

Textbook Question

Answer the following questions about the mechanism for the acid-catalyzed hydration of an alkene:

a. How many transition states are there?

b. How many intermediates are there?

c. Which step in the forward direction has the smallest rate constant?

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

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

Key Concepts

Alkene Reactivity

Electrophilic Addition Reactions

Synthesis Strategies

Watch next

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