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

Previous problemNext problem

3:41 minutes

Problem 26c

Textbook Question

Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
c. 2-methylhexan-3-ol

Verified step by step guidance

Identify the target alcohol: The compound 2-methylhexan-3-ol is a secondary alcohol, meaning the hydroxyl group (-OH) is attached to a carbon atom that is bonded to two other carbon atoms. This suggests that the precursor is likely a ketone.

Determine the corresponding carbonyl compound: To synthesize 2-methylhexan-3-ol, the corresponding carbonyl compound would be 2-methylhexan-3-one. This is because reducing a ketone with a reducing agent will yield a secondary alcohol.

Choose an appropriate reducing agent: Common reducing agents for converting ketones to secondary alcohols include sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). NaBH₄ is often preferred for mild conditions.

Write the reaction mechanism: The reduction involves the nucleophilic attack of the hydride ion (H⁻) from the reducing agent on the carbonyl carbon of 2-methylhexan-3-one. This forms an alkoxide intermediate, which is then protonated by water or an acid to yield 2-methylhexan-3-ol.

Summarize the synthesis: Start with 2-methylhexan-3-one as the carbonyl compound. Treat it with NaBH₄ in a suitable solvent (e.g., ethanol or methanol) to reduce the ketone to 2-methylhexan-3-ol. Finally, perform a workup step to isolate the alcohol product.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Reduction of Carbonyl Compounds

Reduction is a chemical reaction that involves the gain of electrons or a decrease in oxidation state. In organic chemistry, carbonyl compounds, such as aldehydes and ketones, can be reduced to alcohols using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4). Understanding the mechanism of this reduction is crucial for synthesizing alcohols from carbonyl precursors.

Structure of 2-methylhexan-3-ol

2-methylhexan-3-ol is a secondary alcohol with a specific carbon skeleton. It consists of a six-carbon chain (hexane) with a methyl group (–CH3) attached to the second carbon and a hydroxyl group (–OH) on the third carbon. Recognizing the structure helps in identifying the appropriate carbonyl compound to reduce in order to achieve the desired alcohol.

Choice of Carbonyl Compound

To synthesize 2-methylhexan-3-ol, one must select the correct carbonyl compound to reduce. The appropriate precursor is 2-methylhexan-3-one, a ketone, which upon reduction will yield the target alcohol. Understanding the relationship between the structure of the desired alcohol and its corresponding carbonyl compound is essential for successful synthesis.

Watch next

Master Reducing Agents with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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

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

(a) octan-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.

a. heptan-1-ol

Textbook Question

Predict the products of the following reactions.

(d) product of (c) + H₂, Pt

Textbook Question

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(a) butan-1-ol → butanal, CH₃CH₂CH₂CHO

(b) but-2-en-1-ol → but-2-enoic acid, CH₃CH=CH–COOH

Textbook Question

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

Show more practices