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

Alkyne Hydration

Organic Chemistry

10. Addition Reactions

Alkyne Hydration

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3:49 minutes

Problem 34g

Textbook Question

What reagents should be used to carry out the following syntheses?

Verified step by step guidance

Identify the starting material and the product. The starting material is an alkyne, and the product is a ketone.

Recognize that the transformation involves the conversion of an alkyne to a ketone, which suggests a hydration reaction.

Consider the reagents typically used for the hydration of alkynes to form ketones. One common method is the use of mercuric sulfate (HgSO4) in the presence of sulfuric acid (H2SO4) and water (H2O).

Understand that this reaction proceeds via the formation of an enol intermediate, which tautomerizes to form the ketone.

Conclude that the appropriate reagents for this synthesis are HgSO4, H2SO4, and H2O, which will convert the alkyne to the desired ketone through acid-catalyzed hydration.

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Key Concepts

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

Alkyne Hydration

Alkyne hydration is a chemical reaction where an alkyne reacts with water in the presence of an acid catalyst to form a carbonyl compound, typically a ketone or aldehyde. This reaction involves the addition of water across the triple bond of the alkyne, leading to the formation of an enol that tautomerizes to the more stable carbonyl compound.

Reagents for Hydration

The typical reagents used for alkyne hydration include water (H2O), an acid catalyst such as sulfuric acid (H2SO4), and sometimes mercuric sulfate (HgSO4) to facilitate the reaction. The acid catalyst protonates the alkyne, making it more electrophilic and allowing for the nucleophilic attack by water, ultimately leading to the desired carbonyl product.

Tautomerization

Tautomerization is a chemical process where a compound exists in two interconvertible forms, typically involving the migration of a hydrogen atom and a switch of a double bond. In the context of alkyne hydration, the enol formed initially is less stable and quickly converts to the more stable keto form, which is the final product of the reaction.

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Related Practice

Textbook Question

What are products of the following reactions?

Textbook Question

When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.

Textbook Question

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or terminal alkynes. Show what the products would be from hydration of each compound.

e. 3-methylcyclodecyne

Textbook Question

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or terminal alkynes. Show what the products would be from hydration of each compound.

c. hex-1-yne

Textbook Question

For each of the following ketones/aldehydes, indicate whether it is possible to synthesize it from an alkyne as the only compound in good ( > 50%) yield. If so, how would you do it?

(a)

Textbook Question

Answer Problem 39, parts a–h, using 2-butyne as the starting material instead of propyne.

e. aqueous H₂SO₄, HgSO₄

Textbook Question

How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?

Multiple Choice

Predict the major, organic product for the following reaction.

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