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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2:38 minutes

Problem 25e

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)

Verified step by step guidance

Step 1: Analyze the structure of the compound provided. The molecule contains three carbonyl groups: an aldehyde (-CHO), a ketone (C=O), and an ester (-COOCH3). Each of these functional groups reacts differently with LiAlH4.

Step 2: Understand the role of LiAlH4 (Lithium Aluminum Hydride). It is a strong reducing agent that reduces aldehydes, ketones, and esters to their corresponding alcohols. The reaction typically involves the addition of hydride ions (H-) to the carbonyl carbon.

Step 3: Predict the reduction of the aldehyde group (-CHO). LiAlH4 will reduce the aldehyde to a primary alcohol (-CH2OH). This occurs because the hydride ion attacks the carbonyl carbon, followed by protonation during hydrolysis.

Step 4: Predict the reduction of the ketone group (C=O). LiAlH4 will reduce the ketone to a secondary alcohol (-CHOH). The hydride ion attacks the carbonyl carbon, and hydrolysis provides the proton to complete the alcohol formation.

Step 5: Predict the reduction of the ester group (-COOCH3). LiAlH4 reduces esters to primary alcohols. The ester group will be cleaved, producing methanol (CH3OH) and a primary alcohol derived from the remaining carbon chain. Hydrolysis ensures the completion of the reaction.

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Key Concepts

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

Lithium Aluminum Hydride (LiAlH4) Reactivity

LiAlH4 is a strong reducing agent commonly used in organic chemistry to reduce carbonyl compounds, such as aldehydes and ketones, to their corresponding alcohols. It donates hydride ions (H-) to the electrophilic carbon of the carbonyl group, facilitating the conversion of the carbonyl compound into an alcohol. Understanding its reactivity is crucial for predicting the products of reactions involving carbonyl-containing compounds.

Hydrolysis of Alkoxides

After the reduction of a carbonyl compound by LiAlH4, the resulting alkoxide intermediate can undergo hydrolysis when treated with water or an alcohol like methanol. This process involves the protonation of the alkoxide to form the corresponding alcohol. Recognizing the hydrolysis step is essential for determining the final products of the reaction sequence.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves both as a solvent and as a reactant during hydrolysis. Understanding how solvents can stabilize intermediates, affect reaction rates, and participate in reactions is important for accurately predicting the products of the reaction sequence involving LiAlH4 and hydrolysis.

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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.

(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

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

(d) a carboxylic acid

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

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)

Textbook Question

Predict the products of the following reactions:

(a)

(b)

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(b)

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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)

Key Concepts

Lithium Aluminum Hydride (LiAlH4) Reactivity

Hydrolysis of Alkoxides

Solvent Effects in Organic Reactions

Watch next

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)