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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3:25 minutes

Problem 57c,d

Textbook Question

Show how this 1° alcohol can be made from the following:

(c) a 7-carbon aldehyde
(d) a carboxylic acid

Verified step by step guidance

Step 1: Identify the target molecule, which is a primary alcohol with a cyclopentyl group attached to a 2-carbon chain ending in a hydroxyl group (-OH).

Step 2: For part (c), starting from a 7-carbon aldehyde, use a reduction reaction. The aldehyde can be reduced to a primary alcohol using a reducing agent such as sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). Write the reaction as:

R_{2} - C = O + H {NaBH}_{4} \to R_{2} - CH - OH

Step 3: For part (d), starting from a carboxylic acid, first convert the carboxylic acid to an aldehyde. This can be achieved using a mild reducing agent such as DIBAL-H (diisobutylaluminum hydride) under controlled conditions. Write the reaction as:

R - COOH + DIBAL \to R - CHO

Step 4: After obtaining the aldehyde from the carboxylic acid, proceed with the reduction step as described in Step 2 to convert the aldehyde into the primary alcohol.

Step 5: Verify the structure of the final product to ensure it matches the target molecule, confirming that the cyclopentyl group and the hydroxyl group are correctly positioned.

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Key Concepts

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

Alcohol Synthesis

Alcohols can be synthesized through various methods, including reduction reactions. A primary (1°) alcohol can be formed by reducing an aldehyde or a carboxylic acid. Understanding the reduction process, which involves the addition of hydrogen or the removal of oxygen, is crucial for converting carbonyl compounds into alcohols.

Aldehyde Reduction

Aldehydes can be reduced to primary alcohols using reducing agents such as lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4). This reaction involves the nucleophilic attack of the hydride ion on the carbonyl carbon, leading to the formation of the alcohol. Recognizing the structure and reactivity of aldehydes is essential for this transformation.

Carboxylic Acid Reduction

Carboxylic acids can be reduced to primary alcohols through a similar process, typically requiring stronger reducing agents like LiAlH4. The reduction involves the conversion of the carboxyl group (-COOH) to a hydroxyl group (-OH), resulting in the formation of a primary alcohol. Understanding the mechanism of this reduction is vital for synthesizing alcohols from carboxylic acids.

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Related Practice

Textbook Question

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(d) Ph₂CHOH

(e) PhCH₂OH

(f) PhCOOH

Textbook Question

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

(d)

Textbook Question

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

(i) HO–(CH₂)₈–OH

Textbook Question

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

(d)

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.

(e)

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.

(e)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(j)

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.

(d)

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Show how this 1° alcohol can be made from the following:(c) a 7-carbon aldehyde(d) a carboxylic acid

Key Concepts

Alcohol Synthesis

Aldehyde Reduction

Carboxylic Acid Reduction

Watch next

Show how this 1° alcohol can be made from the following:

(c) a 7-carbon aldehyde
(d) a carboxylic acid