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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Problem 88a(ii)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.'
(a)

Verified step by step guidance

Step 1: Recognize the reaction type. The reagents provided, Hg(OAc)₂ followed by NaBH₄, indicate an oxymercuration-demercuration reaction. This reaction is used to hydrate alkenes (add water across a double bond) without carbocation rearrangement.

Step 2: Identify the functional group in the starting molecule. Check if the molecule contains an alkene (C=C double bond), as this reaction specifically targets alkenes.

Step 3: Understand the mechanism. In the first step, Hg(OAc)₂ reacts with the alkene to form a mercurinium ion intermediate. Water then attacks the more substituted carbon of the intermediate, leading to the addition of an -OH group. In the second step, NaBH₄ reduces the mercury group, replacing it with a hydrogen atom.

Step 4: Predict the product. The final product will be an alcohol, with the -OH group added to the more substituted carbon of the original double bond (Markovnikov addition). If the starting molecule does not contain an alkene, there will be no reaction.

Step 5: Verify the conditions. Ensure that the reaction conditions are suitable for the starting molecule. If the molecule lacks a double bond or has functional groups incompatible with the reaction, write 'no reaction.'

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Key Concepts

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

Mercuration-Demercuration

The mercuration-demercuration reaction is a two-step process used to convert alkenes into alcohols. In the first step, mercuric acetate (Hg(OAc)₂) adds to the double bond of the alkene, forming a mercurinium ion. The second step involves the reduction of this intermediate by sodium borohydride (NaBH₄), which replaces the mercury with a hydrogen atom, yielding an alcohol.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of mercuration, the reaction typically follows Markovnikov's rule, where the more substituted carbon atom of the alkene becomes bonded to the mercury, leading to the formation of the more stable carbocation intermediate.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state by a molecule. In the context of the mercuration-demercuration process, sodium borohydride acts as a reducing agent, facilitating the conversion of the mercurinium ion to an alcohol by donating electrons and protons, effectively replacing the mercury with a hydrogen atom.

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Related Practice

Textbook Question

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

(k)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(a)

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(h)

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)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(d)

Textbook Question

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(c)

Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(a)

Textbook Question

In 1973, Caine and Tuller reported a synthesis of racemic oplapanone, a sesquiterpene isolated from Oplopanax japonicus (a deciduous shrub) involving a reaction we learned in this chapter. Predict the product of the reaction shown. (Caine, D.; Tuller, F. N. J. Org. Chem. 1973, 38, 3663.)

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Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)2 2. NaBH4.If there is no reaction, write 'no reaction.' (a)

Key Concepts

Mercuration-Demercuration

Regioselectivity

Reduction Reactions

Watch next

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)₂ 2. NaBH₄.If there is no reaction, write 'no reaction.'
(a)