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

9. Alkenes and Alkynes

Dehydration Reaction

Organic Chemistry

9. Alkenes and Alkynes

Dehydration Reaction

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Problem 41c

Textbook Question

Identify the alcohol(s) that would produce the following alkenes under the given conditions.
(c)

Verified step by step guidance

Step 1: Recognize the reaction type. The given reaction involves the dehydration of an alcohol to form an alkene using concentrated sulfuric acid (H₂SO₄). This is an elimination reaction (E1 mechanism).

Step 2: Analyze the structure of the alkene product. The product is a substituted cyclopentene with a double bond between the cyclopentane ring and the isopropyl group. This suggests that the alcohol precursor must have a hydroxyl group (-OH) attached to the carbon that loses water during the reaction.

Step 3: Determine the alcohol precursor. To form the given alkene, the alcohol must have the hydroxyl group on the carbon adjacent to the cyclopentane ring and the isopropyl group. This ensures that the double bond forms in the correct position during elimination.

Step 4: Consider regioselectivity and stability. The major product of an E1 reaction is typically the more stable alkene, which follows Zaitsev's rule. The double bond forms in the position that results in the most substituted alkene, as seen in the product structure.

Step 5: Identify the alcohol(s). Based on the structure of the alkene, the alcohol precursor is likely 1-(1-hydroxyethyl)cyclopentane or a similar compound where the hydroxyl group is positioned to allow elimination and formation of the observed alkene.

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Key Concepts

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

Alcohols and Alkenes

Alcohols are organic compounds containing one or more hydroxyl (-OH) groups, while alkenes are hydrocarbons that contain at least one carbon-carbon double bond. The conversion of alcohols to alkenes typically involves dehydration, where water is removed, leading to the formation of a double bond. Understanding the structure of both alcohols and alkenes is crucial for predicting the products of such reactions.

Dehydration Reaction

Dehydration reactions involve the removal of a water molecule from a compound, often resulting in the formation of a double bond. In the context of alcohols, this process can be facilitated by heat and the presence of an acid catalyst, which helps to protonate the hydroxyl group, making it a better leaving group. Recognizing the conditions that favor dehydration is essential for determining which alcohols can yield specific alkenes.

Regioselectivity and Zaitsev's Rule

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. Zaitsev's Rule states that in elimination reactions, the more substituted alkene (the one with more alkyl groups attached to the double bond) is typically favored. This principle is important when predicting which alcohols will produce specific alkenes, as it guides the expected outcome based on the stability of the resulting alkenes.

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Identify the alcohol(s) that would produce the following alkenes under the given conditions.(c)

Key Concepts

Alcohols and Alkenes

Dehydration Reaction

Regioselectivity and Zaitsev's Rule

Watch next

Identify the alcohol(s) that would produce the following alkenes under the given conditions.
(c)