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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1:41 minutes

Problem 25d

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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Identify the functional group in the given compound. The structure shows a six-membered cyclic ketone (cyclohexanone) with a carbonyl group (C=O).

Understand the role of LiAlH4 (Lithium Aluminum Hydride). It is a strong reducing agent that reduces ketones to secondary alcohols by adding hydrogens to the carbonyl group.

Write the mechanism of the reaction. LiAlH4 donates a hydride ion (H⁻) to the carbonyl carbon, breaking the double bond and forming an alkoxide intermediate.

Perform hydrolysis. The alkoxide intermediate reacts with water during the hydrolysis step to form the final alcohol product.

Predict the product. The ketone (cyclohexanone) is reduced to a secondary alcohol (cyclohexanol) with the hydroxyl group (-OH) replacing the carbonyl group.

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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 can also reduce esters and carboxylic acids, making it a versatile reagent in organic synthesis. 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 be hydrolyzed by adding water or an alcohol, such as methanol. This hydrolysis step converts the alkoxide into an alcohol, which is the final product of the reaction. Recognizing the role of hydrolysis is essential for determining the final products in reduction reactions.

Solvent Effects in Organic Reactions

The choice of solvent can significantly influence the outcome of organic reactions. In this case, methanol serves as both a solvent and a reactant during hydrolysis. Understanding how solvents interact with reactants and products helps predict reaction mechanisms and product distributions, which is vital for accurately forecasting the results of the given reaction.

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Related Practice

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

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 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)

Textbook Question

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

(e)

(f)

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.

(d)

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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.(d)

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.
(d)