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 62

Textbook Question

What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1-hexanol?

Verified step by step guidance

Identify the starting material: 1-hexanol, which is an alcohol with the molecular formula C6H13OH.

Understand the reaction type: Acid-catalyzed dehydration of alcohols typically involves the removal of a water molecule to form an alkene.

Recognize the mechanism: The reaction proceeds via an E1 mechanism, where the alcohol is first protonated by the acid, leading to the formation of a carbocation intermediate.

Consider carbocation rearrangement: The initial carbocation can rearrange to form a more stable carbocation if possible, which can lead to different alkene products.

Determine possible alkenes: From the carbocation intermediate(s), identify the possible alkenes by considering the elimination of a proton from adjacent carbon atoms, leading to the formation of double bonds.

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Key Concepts

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

Dehydration Reaction

A dehydration reaction involves the removal of a water molecule from an alcohol, resulting in the formation of an alkene. In the case of 1-hexanol, this reaction is typically acid-catalyzed, meaning an acid is used to facilitate the removal of the hydroxyl group and a hydrogen atom from adjacent carbon atoms, leading to the formation of a double bond.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle is crucial in predicting the major products of dehydration reactions, as it helps determine the stability of the resulting alkenes based on the carbocation intermediates formed during the reaction.

Carbocation Stability

Carbocation stability is a key factor in organic reactions, particularly in dehydration processes. Carbocations are positively charged carbon species that can form during the dehydration of alcohols. The stability of these intermediates increases with the degree of substitution: tertiary carbocations are more stable than secondary, which are more stable than primary. This stability influences the major alkene products formed during the reaction.

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Related Practice

Textbook Question

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

Textbook Question

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

Textbook Question

Explain why (S)-2-butanol forms a racemic mixture when it is heated in sulfuric acid.

Textbook Question

Propose a mechanism for the following reaction:

Textbook Question

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

Textbook Question

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

Textbook Question

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with H₂SO₄.

Textbook Question

Propose mechanisms for the following reactions.

(b)

HINT: Alcohol dehydrations usually go through E1 elimination of the protonated alcohol, with a carbocation intermediate. Rearrangements are common.

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