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

Hydroboration

Organic Chemistry

10. Addition Reactions

Hydroboration

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Problem 61b(vi)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH
(b)

Verified step by step guidance

Step 1: Recognize the reaction type. The given conditions (1. BH₃, 2. H₂O₂, NaOH) indicate hydroboration-oxidation, which is a method for converting alkenes into alcohols.

Step 2: Understand the regioselectivity of hydroboration-oxidation. This reaction follows anti-Markovnikov addition, meaning the hydroxyl group (-OH) will attach to the less substituted carbon of the double bond.

Step 3: Consider the stereochemistry. Hydroboration-oxidation proceeds with syn addition, meaning the hydrogen and hydroxyl group will add to the same face of the alkene.

Step 4: Identify the structure of the starting alkene. Analyze the position of the double bond and determine which carbon is less substituted to predict where the hydroxyl group will attach.

Step 5: Draw the product. After determining the regioselectivity and stereochemistry, sketch the resulting alcohol, ensuring the hydroxyl group is on the less substituted carbon and both groups are added syn to each other.

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Key Concepts

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

Hydroboration-Oxidation

Hydroboration-oxidation is a two-step reaction process used to convert alkenes into alcohols. In the first step, borane (BH₃) adds across the double bond of the alkene, resulting in a trialkylborane intermediate. The second step involves oxidation with hydrogen peroxide (H₂O₂) in the presence of a base (NaOH), which converts the boron atom into a hydroxyl group, yielding an alcohol.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In hydroboration, the addition of borane occurs in a syn fashion, favoring the formation of the less substituted alcohol due to the mechanism's anti-Markovnikov nature, where the hydroxyl group ends up on the less substituted carbon of the alkene.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the hydroboration-oxidation reaction, the syn addition of borane leads to specific stereochemical outcomes, which can influence the properties and reactivity of the resulting alcohol. Understanding stereochemistry is crucial for predicting the 3D orientation of the product.

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Related Practice

Textbook Question

Predict the major products of the following reactions.

a. propene + BH₃⋅THF

b. the product from part (a) + H₂O₂/OH⁻

Textbook Question

Show how you would make the following compounds from a suitable cyclic alkene.

(e)

Textbook Question

Show how you would accomplish the following transformations.

(b)

Textbook Question

Suggest an alkene to undergo hydroboration–oxidation (1. BH₃ 2. NaOH, H₂O₂) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.

(d)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH

(g)

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH

(k)

Textbook Question

Show a mechanism for the formation of one isomer in each of the reactions in Assessment 9.1.

(c)

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.

(g)

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Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH3 2. H2O2, NaOH (b)

Key Concepts

Hydroboration-Oxidation

Regioselectivity

Stereochemistry

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Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH₃ 2. H₂O₂, NaOH
(b)