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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4:18 minutes

Problem 14d

Textbook Question

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

Verified step by step guidance

Step 1: Identify the starting material and the type of alcohol desired (primary, secondary, or tertiary). This will help determine the appropriate reagent and reaction pathway.

Step 2: If the starting material is an alkene, consider using hydroboration-oxidation (BH₃ followed by H₂O₂/NaOH) or oxymercuration-demercuration (Hg(OAc)₂ followed by NaBH₄) to convert the alkene into an alcohol.

Step 3: If the starting material is a carbonyl compound (aldehyde or ketone), use a reducing agent such as NaBH₄ or LiAlH₄ to reduce the carbonyl group to an alcohol. NaBH₄ is suitable for mild reductions, while LiAlH₄ is more reactive and can reduce esters and carboxylic acids as well.

Step 4: If the starting material is an alkyl halide, consider using aqueous NaOH or KOH for nucleophilic substitution to form an alcohol. Alternatively, you can use Ag₂O in water for a gentler conversion.

Step 5: If the starting material is an ester or carboxylic acid, use LiAlH₄ followed by acidic workup to reduce the compound to an alcohol. This reagent is strong enough to break the ester bond and reduce carboxylic acids.

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Key Concepts

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

Alcohol Functional Group

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. Understanding the structure and reactivity of alcohols is crucial for predicting how they can be synthesized or converted from other functional groups. The properties of alcohols, such as polarity and hydrogen bonding, influence their behavior in chemical reactions.

Reduction Reactions

Reduction reactions involve the gain of electrons or the addition of hydrogen to a molecule, often resulting in the conversion of carbonyl compounds (like aldehydes or ketones) to alcohols. Common reducing agents include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). Recognizing the type of carbonyl compound and the appropriate reducing agent is essential for successfully converting it to an alcohol.

Reagents for Alcohol Synthesis

Various reagents can be employed to synthesize alcohols from different starting materials. For example, Grignard reagents can react with carbonyl compounds to form alcohols, while hydrolysis of alkyl halides can also yield alcohols. Understanding the specific reagents and their mechanisms of action is vital for selecting the correct one for a given conversion.

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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

(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

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

b. cyclohexylmethanol

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.

Textbook Question

Identify A through O:

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