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

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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1:29 minutes

Problem 84c

Textbook Question

How can the following compounds be prepared from the given starting materials?
c.

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is cyclohexyl bromide, and the target compound is cyclohexylacetic acid. This transformation involves replacing the bromine atom with a carboxylic acid functional group.

Step 2: Perform a nucleophilic substitution reaction. Treat cyclohexyl bromide with cyanide ion (e.g., NaCN or KCN) to replace the bromine atom with a nitrile group, forming cyclohexylacetonitrile. This is an SN2 reaction where the cyanide ion acts as the nucleophile.

Step 3: Hydrolyze the nitrile group to a carboxylic acid. Subject cyclohexylacetonitrile to acidic or basic hydrolysis (e.g., HCl/H2O or NaOH/H2O) to convert the nitrile group (-CN) into a carboxylic acid (-COOH), yielding cyclohexylacetic acid.

Step 4: Purify the product. After hydrolysis, isolate and purify the cyclohexylacetic acid using techniques such as extraction, recrystallization, or distillation, depending on the reaction conditions and impurities.

Step 5: Verify the structure of the product. Use spectroscopic methods such as IR (to confirm the presence of the carboxylic acid group) and NMR (to confirm the structure of cyclohexylacetic acid) to ensure the desired compound has been synthesized.

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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 attacks an electrophilic carbon atom, replacing a leaving group. In this case, the bromine atom (a good leaving group) is substituted by a hydroxyl group (OH), forming an alcohol. Understanding the mechanism of this reaction, including the role of nucleophiles and the stability of intermediates, is crucial for predicting the outcome of the transformation.

Reactivity of Alkyl Halides

Alkyl halides, such as the brominated compound in the question, are reactive due to the polar C-X bond, where X is a halogen. The carbon atom bonded to the halogen is electrophilic, making it susceptible to nucleophilic attack. The structure of the alkyl halide, including steric hindrance and the nature of the halogen, influences the reaction pathway (SN1 or SN2) and the rate of substitution, which is essential for understanding how to prepare the desired alcohol.

Formation of Alcohols

Alcohols can be synthesized from various organic compounds through different methods, including nucleophilic substitution of alkyl halides. In this reaction, the hydroxide ion (OH-) acts as a nucleophile, attacking the carbon atom bonded to the bromine, leading to the formation of an alcohol. Recognizing the conditions and reagents required for this transformation, such as the use of a strong base or water, is vital for successfully preparing alcohols from halogenated starting materials.

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