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

Oxymercuration

Organic Chemistry

10. Addition Reactions

Oxymercuration

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5:19 minutes

Problem 44c(vi)

Textbook Question

For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vi) H₂SO₄, HgSO₄, H₂O. If you expect two products, show both.
(c)

Verified step by step guidance

Identify the alkyne structure provided in the problem. Determine whether it is a terminal alkyne (triple bond at the end of the chain) or an internal alkyne (triple bond within the chain). This distinction is important for predicting the product.

Understand the reaction conditions: H₂SO₄ (sulfuric acid), HgSO₄ (mercuric sulfate), and H₂O (water). These conditions promote the hydration of alkynes, leading to the formation of a ketone via the Markovnikov addition of water across the triple bond.

Apply the mechanism: The alkyne reacts with H₂O in the presence of H₂SO₄ and HgSO₄. First, the alkyne is protonated to form a carbocation intermediate. The Hg²⁺ ion stabilizes the carbocation, and water adds to the more substituted carbon (Markovnikov addition).

Recognize the enol intermediate: The addition of water forms an enol (a compound with a hydroxyl group attached to a carbon-carbon double bond). This enol is unstable and undergoes tautomerization to form a ketone. Tautomerization involves the migration of a proton and the rearrangement of the double bond.

If the alkyne is symmetrical, a single ketone product will form. If the alkyne is asymmetrical, two possible ketone products may form due to the different substituents on either side of the triple bond. Analyze the structure of the alkyne to determine whether one or two products are expected.

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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, typically sulfuric acid (H₂SO₄) and a mercury(II) salt (HgSO₄). This process leads to the formation of an enol, which can tautomerize to a more stable ketone. Understanding this reaction is crucial for predicting the products formed when alkynes are treated under these conditions.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen or OH) to an alkene or alkyne, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of the reaction, guiding the formation of the major product when alkynes undergo hydration.

Tautomerization

Tautomerization is a chemical process where a compound exists in two interconvertible forms, typically involving the relocation of a proton and a shift of a double bond. In the context of alkyne hydration, the initial enol product can convert to a ketone through tautomerization, which is often the more stable and predominant form. Recognizing this process is essential for identifying all possible products of the reaction.

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Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

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