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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2:44 minutes

Problem 53c

Textbook Question

Show how each of the following compounds can be synthesized from an alkene:
c.

Verified step by step guidance

Step 1: Identify the target compound. The given compound is cyclopentylmethanol, which contains a cyclopentane ring and a hydroxymethyl (-CH2OH) group attached to it.

Step 2: Choose an appropriate alkene precursor. The precursor alkene should be cyclopentene, as it contains the cyclopentane ring structure and can be functionalized to introduce the hydroxymethyl group.

Step 3: Plan the reaction to introduce the hydroxymethyl group. Use hydroboration-oxidation, a two-step reaction that converts an alkene into an alcohol. In the first step, react cyclopentene with diborane (B2H6) or BH3·THF to form an organoborane intermediate. This step ensures anti-Markovnikov addition, where the boron atom attaches to the less substituted carbon of the double bond.

Step 4: Oxidize the organoborane intermediate. Treat the intermediate with hydrogen peroxide (H2O2) in the presence of a base (such as NaOH). This step replaces the boron atom with a hydroxyl group (-OH), forming cyclopentylmethanol.

Step 5: Verify the product. Ensure that the hydroxymethyl group is attached to the correct carbon (anti-Markovnikov position) and that the cyclopentane ring remains intact.

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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, an alkene reacts with diborane (B2H6) to form an organoborane intermediate, which adds across the double bond in a syn addition manner. The second step involves oxidation of the organoborane with hydrogen peroxide (H2O2) in a basic solution, resulting in the formation of an alcohol with anti-Markovnikov orientation.

Markovnikov's Rule

Markovnikov's Rule states that when HX (where X is a halogen or hydroxyl group) adds to an asymmetric alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This rule helps predict the major product of electrophilic addition reactions, guiding the synthesis of compounds from alkenes by indicating where functional groups will be added.

Stereochemistry of Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions like hydroboration, the stereochemical outcome is important because it can lead to the formation of specific isomers. Understanding stereochemistry is crucial for predicting the configuration of the final product, especially in reactions that involve chiral centers or require specific stereochemical orientations.

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Related Practice

Textbook Question

Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)₂ , H₂O 2. NaBH₄ ].

(b)

Multiple Choice

Indentify the mechanism of reaction and predict the product.

Multiple Choice

Predict the product of the following reaction.

Textbook Question

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents:

c. R₂BH/THF, followed by HO^–, H₂O₂, H₂O

Textbook Question

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

2. BH₃/THF, followed by HO^-, H₂O₂, H₂O

Textbook Question

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

d. (Z)-3,4-dimethyl-3-hexene

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?

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