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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2:36 minutes

Problem 47a

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

a. borane in tetrahydrofuran, followed by basic hydrogen peroxide

Verified step by step guidance

Identify the functional groups in limonene: Limonene is a terpene with a characteristic double bond in its structure. This double bond is the site of reactivity in the reaction with borane.

Understand the hydroboration-oxidation reaction: This reaction involves two main steps. First, the addition of borane (BH3) to the double bond, followed by oxidation with hydrogen peroxide (H2O2) in a basic solution.

Predict the regioselectivity of hydroboration: In the hydroboration step, borane adds across the double bond in an anti-Markovnikov fashion, meaning the boron atom attaches to the less substituted carbon of the double bond.

Perform the oxidation step: The boron atom is replaced by a hydroxyl group (-OH) during the oxidation step with hydrogen peroxide in a basic medium, resulting in the formation of an alcohol.

Draw the final product: The final product will be an alcohol where the hydroxyl group is attached to the less substituted carbon of the original double bond in limonene, reflecting the anti-Markovnikov addition.

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Key Concepts

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

Limonene Structure and Reactivity

Limonene is a cyclic monoterpene with a double bond, which makes it reactive in various organic reactions. Understanding its structure is crucial for predicting the products of its reactions. The presence of the double bond allows for electrophilic addition reactions, where reagents can add across the double bond, leading to different functional groups in the products.

Hydroboration-Oxidation Reaction

The hydroboration-oxidation reaction is a two-step process used to convert alkenes into alcohols. In the first step, borane (BH3) adds across the double bond of limonene, forming an organoborane intermediate. The subsequent oxidation with hydrogen peroxide in a basic medium converts the organoborane into an alcohol, typically resulting in anti-Markovnikov addition of water across the double bond.

Stereochemistry of Reaction Products

Stereochemistry refers to the spatial arrangement of atoms in molecules and is crucial in determining the properties of the reaction products. The addition of reagents to limonene can lead to different stereoisomers, depending on the mechanism of the reaction. Understanding stereochemistry helps predict the specific configurations of the alcohol products formed after hydroboration-oxidation.

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Related Practice

Textbook Question

The bulky borane 9-BBN was developed to enhance the selectivity of hydroboration. In this example, 9-BBN adds to the less hindered carbon with 99.3% regioselectivity, compared with only 57% for diborane.

b. 9-BBN is synthesized by adding BH₃ across a symmetric, cyclic diene. What is the structure of the diene?

Textbook Question

Show how you would accomplish the following synthetic conversions.

(b) but-1-ene → butan-2-ol

Textbook Question

Show how you would synthesize the following alcohol from appropriate alkene.

(b)

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

d. trans-2-methylcyclohexanol

Textbook Question

Unlike hydroboration–oxidation, the addition of H₂O catalyzed by H₃O⁺ is not stereospecific. Thinking carefully about the mechanism of the reaction, give two reasons why.

Textbook Question

Draw the products of the following reactions, including their configurations:

Textbook Question

What reagents are needed to carry out the following syntheses?

Textbook Question

Explain why, in hydroboration–oxidation, HO⁻ and HOOH cannot be added until after the hydroboration reaction is over.

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