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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2:43 minutes

Problem 52e

Textbook Question

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons:
e.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is cyclohexylacetylene (cyclohexane with a terminal alkyne group), and the target compound is cyclohexyl methyl ketone (cyclohexane with a methyl ketone group). This transformation involves converting the terminal alkyne into a methyl ketone.

Step 2: Recognize the reaction type. The conversion of a terminal alkyne to a methyl ketone can be achieved through hydration of the alkyne followed by tautomerization. This reaction typically uses a catalyst such as HgSO₄ (mercuric sulfate) in the presence of H₂SO₄ (sulfuric acid) and water.

Step 3: Write the reaction mechanism. The terminal alkyne undergoes electrophilic addition of water in the presence of the Hg²⁺ catalyst. This forms an enol intermediate (a compound with a hydroxyl group attached to a double-bonded carbon). The enol then tautomerizes to form the ketone.

Step 4: Specify the reagents. To perform this reaction, use HgSO₄, H₂SO₄, and H₂O. These reagents facilitate the hydration of the alkyne and the subsequent tautomerization to yield the methyl ketone.

Step 5: Confirm the carbon count. Since the target compound has a methyl group (one carbon) added to the cyclohexane ring, the reaction adheres to the restriction of using organic compounds with no more than four carbons.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding the functional groups present in both the starting materials and the target compounds is essential for predicting the types of reactions that can occur and for designing synthetic pathways.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step sequence of elementary reactions by which overall chemical change occurs. Familiarity with common mechanisms, such as nucleophilic substitution or elimination reactions, is crucial for determining how to convert starting materials into desired products effectively.

Reagents and Conditions

The choice of reagents and reaction conditions (such as temperature, solvent, and pressure) significantly influences the outcome of a chemical reaction. Knowing which inorganic reagents and organic compounds can be used, along with the appropriate conditions, is vital for successfully synthesizing the target compounds from the given starting materials.

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Related Practice

Textbook Question

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(c)

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?

(d)

Textbook Question

Which alkyne should be used for the synthesis of each of the following ketones?

Textbook Question

Which alkyne should be used for the synthesis of each of the following ketones?

Textbook Question

What ketones are formed from the acid-catalyzed hydration of 3-heptyne?

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

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Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any ­organic compound that has no more than four carbons:e.

Key Concepts

Functional Groups

Reaction Mechanisms

Reagents and Conditions

Watch next

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons:
e.