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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5:26 minutes

Problem 58b

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)

Verified step by step guidance

Step 1: Analyze the first reaction. Bromocyclohexane reacts with KOH in ethanol under heat (Δ). This is an elimination reaction where the bromine atom is removed, and a double bond is formed in the cyclohexane ring, resulting in cyclohexene (compound A).

Step 2: Examine the second reaction. Cyclohexene (compound A) reacts with KMnO4 in NaOH under heat (Δ). This is an oxidative cleavage reaction where the double bond in cyclohexene is broken, forming a dicarboxylic acid (compound E).

Step 3: Consider the third reaction. The dicarboxylic acid (compound E) is treated with LiAlH4 in ether. LiAlH4 is a strong reducing agent that reduces carboxylic acids to primary alcohols, resulting in a diol (compound F).

Step 4: The final step involves the diol (compound F) being treated with dilute H3O+. This step ensures the reaction is complete and neutralizes any remaining basic conditions from the previous step.

Step 5: Summarize the transformations. Bromocyclohexane undergoes elimination to form cyclohexene, oxidative cleavage to form a dicarboxylic acid, and reduction to form a diol, followed by neutralization.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, bromocyclohexane undergoes nucleophilic substitution with KOH in ethanol, leading to the formation of an alcohol. Understanding this mechanism is crucial for predicting the products of the reaction and the subsequent steps in the synthesis.

Oxidation Reactions

Oxidation reactions involve the increase of oxidation state of a molecule, often through the addition of oxygen or the removal of hydrogen. In the provided synthesis, the intermediate A is oxidized using KMnO4 in a basic medium, which typically converts alcohols to carbonyl compounds or carboxylic acids. Recognizing the role of oxidizing agents is essential for predicting the transformation of intermediates in organic synthesis.

Reduction Reactions

Reduction reactions are processes that decrease the oxidation state of a molecule, often involving the addition of hydrogen or the removal of oxygen. In this synthesis, LiAlH4 is used to reduce the carbonyl compound E to an alcohol F. Understanding reduction mechanisms is vital for determining how functional groups can be transformed in organic synthesis.

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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.

(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

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)

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.

(f)

Textbook Question

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

(k)

(l)

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