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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4:56 minutes

Problem 52b

Textbook Question

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

Verified step by step guidance

Step 1: Begin by identifying the functional group transformation required. Methylenecyclohexane is an alkene, and cyclohexylmethanol is an alcohol. This indicates that the synthesis involves converting the alkene to an alcohol.

Step 2: Use hydroboration-oxidation to achieve the anti-Markovnikov addition of water to the alkene. First, react methylenecyclohexane with diborane (B₂H₆) or BH₃·THF to form the organoborane intermediate.

Step 3: Oxidize the organoborane intermediate using hydrogen peroxide (H₂O₂) in the presence of a base, such as sodium hydroxide (NaOH). This step converts the boron group into a hydroxyl group, yielding cyclohexylmethanol.

Step 4: Verify the regioselectivity of the reaction. Hydroboration-oxidation adds the hydroxyl group to the less substituted carbon of the double bond, ensuring the correct product formation.

Step 5: Purify the product using techniques such as distillation or recrystallization, depending on the physical properties of cyclohexylmethanol, to ensure a pure compound.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones through a series of chemical reactions. Understanding the principles of synthesis is crucial for devising pathways to create specific compounds, such as cyclohexylmethanol from methylenecyclohexane. This involves selecting appropriate reagents and reaction conditions to achieve the desired transformation.

Reagents and Reaction Mechanisms

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Familiarity with various reagents and their mechanisms of action is essential for predicting the outcomes of reactions. For instance, in synthesizing cyclohexylmethanol, one might use reagents like reducing agents or alcohols, and understanding their roles helps in planning the synthesis effectively.

Functional Group Interconversion

Functional group interconversion involves the transformation of one functional group into another within a molecule. This concept is vital in organic synthesis, as it allows chemists to modify compounds to achieve desired properties or reactivity. In the case of synthesizing cyclohexylmethanol, converting a double bond in methylenecyclohexane to an alcohol functional group is a key step in the synthesis process.

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Related Practice

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)

Textbook Question

Suggest a reagent to carry out each of the following conversions to an alcohol.

(d)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH₃ 2. NaOH, H₂O₂ (ii) 1. Hg(OAc)₂ 2. NaBH₄ (iii) H₂SO₄ , H₂O (iv) 1. OsO₄ 2. NaHSO₃ (v) H₂O (vi) NaOH, H₂O . If there is no reaction, write 'no reaction.'

(d)

Textbook Question

Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH₃ 2. NaOH, H₂O₂. If there is no reaction, write 'no reaction.'

(a)

Textbook Question

a. Show the reagents required to form the primary alcohol in each of the following reactions.

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