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 106a(vi)

Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'
(a)

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Identify the functional group in the given molecule. The structure shows a benzene ring with a primary alcohol group attached, known as benzyl alcohol.

Consider the reaction conditions: H₂SO₄ is a strong acid and can act as a dehydrating agent.

Recognize that under acidic conditions, primary alcohols can undergo dehydration to form alkenes. In this case, benzyl alcohol can lose a water molecule to form a double bond.

Propose the mechanism: The hydroxyl group (OH) will be protonated by H₂SO₄, making it a better leaving group. This will lead to the formation of a carbocation.

Predict the product: The carbocation formed can lose a proton to form a double bond, resulting in the formation of styrene (phenylethene) as the major product.

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Key Concepts

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

Acid-Base Reactions

In organic chemistry, acid-base reactions involve the transfer of protons (H⁺) between molecules. Strong acids, like sulfuric acid (H₂SO₄), can donate protons to bases, facilitating various reactions such as dehydration or protonation. Understanding the role of acids and bases is crucial for predicting the outcome of reactions involving functional groups.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, leading to the formation of a more saturated product. In the presence of H₂SO₄, alkenes and alkynes can undergo electrophilic addition, resulting in the formation of carbocations and subsequent products. Recognizing the nature of the reactants helps in predicting the products formed.

Reaction Conditions

The conditions under which a reaction occurs significantly influence the products formed. In this case, the presence of concentrated sulfuric acid can lead to dehydration reactions, where water is removed from alcohols or alkenes, forming alkenes or ethers. Understanding how temperature, concentration, and solvent affect reaction pathways is essential for accurate predictions.

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Related Practice

Textbook Question

When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]

(a)

Textbook Question

Predict the product of the following pinacol rearrangements.

(c)

Textbook Question

Suggest a mechanism for the following reactions.

Textbook Question

Suggest a mechanism for the following substitution reaction.

Textbook Question

The acid-catalyzed hydration we learned here in Chapter 8 is reversible:

Textbook Question

What product is obtained when the following vicinal diol is heated in an acidic solution?

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.

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Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.' (a)

Key Concepts

Acid-Base Reactions

Electrophilic Addition

Reaction Conditions

Watch next

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'
(a)