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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3:47 minutes

Problem 20f

Textbook Question

What are products of the following reactions?
f.

Verified step by step guidance

Step 1: Identify the type of reaction. The given reaction involves an alkyne reacting with water in the presence of sulfuric acid (H₂SO₄). This is an example of an acid-catalyzed hydration of an alkyne.

Step 2: Understand the mechanism. In acid-catalyzed hydration, the alkyne undergoes electrophilic addition of water, facilitated by the acid catalyst. The reaction typically proceeds via the formation of an enol intermediate, which then tautomerizes to form a ketone.

Step 3: Analyze the structure of the alkyne. The alkyne shown is terminal, meaning the triple bond is at the end of the carbon chain. Terminal alkynes typically form methyl ketones as the major product in acid-catalyzed hydration reactions.

Step 4: Predict the intermediate. The addition of water across the triple bond forms an enol intermediate. The enol has a hydroxyl group (-OH) attached to one of the carbons of the former triple bond, and a double bond between the two carbons.

Step 5: Tautomerization to the final product. The enol intermediate undergoes tautomerization, a process where the hydroxyl group and the double bond rearrange to form a ketone. For this reaction, the final product will be a methyl ketone with the carbonyl group (C=O) on the second carbon of the chain.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of products that can be formed in a reaction. Common functional groups include alcohols, carboxylic acids, and amines.

Stoichiometry

Stoichiometry involves the calculation of reactants and products in chemical reactions. It is essential for determining the amounts of substances consumed and produced, ensuring that the law of conservation of mass is upheld. Mastery of stoichiometry allows chemists to balance equations and predict yields of reactions.

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Related Practice

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

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:

Textbook Question

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

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

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

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