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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4:37 minutes

Problem 13c

Textbook Question

Predict the major products of the following reactions. Include stereochemistry where applicable.
(c)

Verified step by step guidance

Step 1: Recognize the reaction type. The given reaction involves hydroboration-oxidation, which is a two-step process used to convert alkenes into alcohols. The first step uses BH3⋅THF (borane in tetrahydrofuran) to add boron and hydrogen across the double bond, and the second step uses H2O2 and OH⁻ to replace the boron with a hydroxyl group.

Step 2: Understand the regioselectivity. Hydroboration-oxidation follows anti-Markovnikov addition, meaning the hydroxyl group (-OH) will be added to the less substituted carbon of the double bond, while the hydrogen will be added to the more substituted carbon.

Step 3: Consider stereochemistry. Hydroboration-oxidation proceeds with syn addition, meaning both the hydrogen and hydroxyl group will be added to the same face of the molecule. This is important for determining the stereochemistry of the product.

Step 4: Analyze the structure of the starting material. The starting material is a bicyclic compound with a double bond. The double bond is between a bridgehead carbon and a secondary carbon. The hydroxyl group will be added to the secondary carbon (less substituted), and the hydrogen will be added to the bridgehead carbon (more substituted).

Step 5: Predict the major product. After the reaction, the hydroxyl group will be added to the less substituted carbon of the double bond, and the hydrogen will be added to the more substituted carbon. Both groups will be added to the same face of the molecule, resulting in a syn addition product. Ensure stereochemistry is properly represented in the final structure.

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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 in a syn addition, resulting in an organoborane intermediate. The second step involves oxidation with hydrogen peroxide (H2O2) and hydroxide (OH-), which replaces the boron atom with a hydroxyl group, yielding an alcohol with anti-Markovnikov orientation.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving chiral centers, the stereochemistry of the products can be crucial. For hydroboration-oxidation, the syn addition of borane leads to specific stereochemical outcomes, which must be considered when predicting the major products of the reaction.

Regioselectivity

Regioselectivity is the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of hydroboration-oxidation, the reaction is regioselective for the formation of alcohols at the less substituted carbon of the alkene, following the anti-Markovnikov rule. Understanding regioselectivity is essential for predicting the major products in reactions involving unsymmetrical alkenes.

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Related Practice

Textbook Question

What stereoisomers are obtained from hydroboration–oxidation of the following compounds? Assign an R or S configuration to each asymmetric center.

c. cis-2-butene

Textbook Question

Which is more highly regioselective: reaction of an alkene with BH₃ or with 9-BBN?

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(c)

Textbook Question

When (E)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers? What is the relationship between the products formed from (Z)-3-methylhex-3-ene and those formed from (E)-3-methylhex-3-ene?

Textbook Question

Predict the major products of the following reactions. Include stereochemistry where applicable.

(b) trans-4,4-dimethylpent-2-ene + BH₃⋅THF then H₂O₂, OH^–

Textbook Question

Predict the major products of the following reactions. Include stereochemistry where applicable.

(a) 1−methylcyclohexene + BH₃⋅THF then H₂O₂, OH^–

Textbook Question

Show how you would accomplish the following synthetic conversions.

a. but-1-ene → butan-1-ol

Textbook Question

Predict the major products of the following reactions.

(d) the product from part (c) + H₂O₂/OH⁻