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

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

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2:49 minutes

Problem 38d

Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.
(d)

Verified step by step guidance

Analyze the target molecule: The alcohol group (-OH) is attached to a secondary carbon. This suggests that the synthesis will involve the Markovnikov addition of water to an alkene.

Identify the appropriate alkene: The target alcohol can be synthesized from an alkene where the double bond is located between the secondary carbon (where the -OH group is attached) and the adjacent carbon. In this case, the alkene would be cyclopentylpropene.

Select the reaction conditions: To achieve Markovnikov addition of water, use an acid-catalyzed hydration reaction. This typically involves using dilute sulfuric acid (H₂SO₄) and water (H₂O) as reagents.

Describe the mechanism: The alkene undergoes protonation by H⁺ from the acid, forming a carbocation intermediate at the more stable secondary carbon. Water then attacks the carbocation, followed by deprotonation to yield the alcohol.

Verify the product: Ensure that the alcohol formed matches the structure of the target molecule, with the -OH group attached to the secondary carbon and the rest of the carbon skeleton intact.

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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. Understanding the nature of the alkene and the conditions under which it reacts is crucial for synthesizing alcohols from alkenes.

Hydroboration-Oxidation

The hydroboration-oxidation reaction is a two-step process used to convert alkenes into alcohols. In the first step, an alkene reacts with borane (BH3) to form an organoborane intermediate, which is then oxidized in the second step using hydrogen peroxide (H2O2) and a base. This method provides a syn-addition of water across the double bond, resulting in the formation of alcohols with anti-Markovnikov selectivity.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen or hydroxyl group) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle is essential for predicting the outcome of reactions involving alkenes and helps in determining the structure of the resulting alcohol when synthesizing from a specific alkene.

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