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

13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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5:52 minutes

Problem 43a

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(a) octan-1-ol

Verified step by step guidance

Step 1: Identify the target alcohol structure. In this case, the target alcohol is benzyl alcohol, which has a benzene ring attached to a CH2OH group.

Step 2: Determine the carbonyl compound that can be reduced to form the target alcohol. Benzyl alcohol can be formed by reducing benzaldehyde (C6H5CHO), which has a benzene ring attached to a CHO group.

Step 3: Select an appropriate reducing agent for the reduction of the carbonyl compound to an alcohol. Common reducing agents include sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4). NaBH4 is milder and typically used for aldehydes and ketones, while LiAlH4 is stronger and can reduce a wider range of compounds.

Step 4: Write the reaction mechanism. The reducing agent donates hydride ions (H-) to the carbonyl carbon of benzaldehyde, breaking the C=O double bond and forming a single bond with an OH group, resulting in benzyl alcohol.

Step 5: Consider reaction conditions. For NaBH4, the reaction is typically carried out in a protic solvent like ethanol or methanol. For LiAlH4, the reaction requires an aprotic solvent like ether and careful handling due to its reactivity.

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Key Concepts

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

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes and ketones, which can be reduced to alcohols. Understanding the structure and reactivity of carbonyl compounds is essential for predicting the products of reduction reactions.

Reducing Agents

Reducing agents are substances that donate electrons in a chemical reaction, thereby reducing another species. Common reducing agents for carbonyl compounds include lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). The choice of reducing agent can influence the reaction conditions and the selectivity of the reduction.

Alcohol Formation

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups. The formation of alcohols from carbonyl compounds involves the addition of hydrogen to the carbonyl carbon, resulting in the conversion of the C=O bond to a C-OH bond. This transformation is a key reaction in organic synthesis and is fundamental to understanding alcohol chemistry.

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Related Practice

Textbook Question

Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(a) CH₃–(CH₂)₈–CHO

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(a) CH₃–(CH₂)₈–CHO

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(b) 1-cyclohexylpropan-1-ol

Textbook Question

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(c)

Textbook Question

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.

c. 2-methylhexan-3-ol

Textbook Question

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.

a. heptan-1-ol

Textbook Question

Predict the products of the following reactions.

(d) product of (c) + H₂, Pt

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Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.(a) octan-1-ol

Key Concepts

Carbonyl Compounds

Reducing Agents

Alcohol Formation

Watch next

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(a) octan-1-ol