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 1c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the reaction type. The reaction shown is hydroboration-oxidation, which involves the addition of water across a double bond in an anti-Markovnikov fashion. This reaction proceeds via syn addition, meaning both the hydrogen and hydroxyl group are added to the same face of the double bond.

Step 2: Examine the starting material. The starting material is an alkene with a double bond in a symmetrical environment. The symmetry of the molecule plays a key role in determining the stereochemical outcome.

Step 3: Consider the stereochemistry of the product. Since hydroboration-oxidation proceeds via syn addition, the stereochemistry of the product depends on the spatial arrangement of the substituents around the double bond. The reaction produces two stereoisomers because the addition can occur on either face of the double bond.

Step 4: Determine if the mixture is equal or unequal. Due to the symmetry of the starting alkene, both faces of the double bond are equally accessible. This results in the formation of an equal mixture of stereoisomers.

Step 5: Conclude the stereochemical outcome. The reaction produces a racemic mixture, meaning the two stereoisomers are formed in equal amounts. This is because the starting material does not have any chiral centers or steric hindrance that would favor one face of the double bond over the other.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This can lead to different physical and chemical properties. In organic chemistry, stereoisomers can be classified into enantiomers and diastereomers, which are crucial for understanding reactivity and product formation in reactions.

Hydroboration-Oxidation

Hydroboration-oxidation is a two-step reaction process used to convert alkenes into alcohols. The first step involves the addition of borane (BH3) to the alkene, resulting in a trialkylborane intermediate. The second step involves oxidation with hydrogen peroxide and sodium hydroxide, yielding an alcohol. This reaction is stereospecific and leads to syn-addition, which is important for determining the stereochemical outcome of the product.

Chirality and Chiral Centers

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of a chiral center, typically a carbon atom bonded to four different substituents. The presence of chiral centers in a molecule can lead to the formation of enantiomers, which are stereoisomers that are mirror images of each other. Understanding chirality is essential for predicting the types of stereoisomers produced in reactions like hydroboration-oxidation.

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Related Practice

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(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)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(d)

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.)

Textbook Question

Assessment 8.74 revealed that oxymercuration could be used to make cyclic esters. Suggest a likely mechanism for this transformation.

Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.

(b)

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

Key Concepts

Stereoisomerism

Hydroboration-Oxidation

Chirality and Chiral Centers

Watch next

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