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

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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6:01 minutes

Problem 53

Textbook Question

Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.

Verified step by step guidance

Identify the reaction mechanism: Bromocyclohexane is a secondary alkyl halide, and hydroxide ion (OH⁻) can act as both a nucleophile and a base. To favor the formation of cyclohexanol (via substitution) over cyclohexene (via elimination), we need to suppress the elimination reaction (E2) and promote the nucleophilic substitution reaction (SN2 or SN1).

Choose reaction conditions: To minimize elimination (E2), use a polar protic solvent (e.g., water or alcohol) that stabilizes the transition state for substitution reactions. Avoid strong heating, as higher temperatures favor elimination reactions.

Select the appropriate nucleophile: Use a dilute solution of hydroxide ion (OH⁻) to ensure that the reaction proceeds primarily via substitution. A high concentration of hydroxide ion can increase the likelihood of elimination.

Explain the substitution mechanism: In the SN2 mechanism, the hydroxide ion attacks the carbon atom bonded to the bromine atom from the opposite side, displacing the bromine atom as a leaving group. This results in the formation of cyclohexanol. If the reaction proceeds via SN1, the bromine atom leaves first, forming a carbocation intermediate, which is then attacked by the hydroxide ion to form cyclohexanol.

Control reaction conditions to suppress elimination: Keep the reaction temperature low and avoid using strong bases or bulky bases, as these favor elimination. Additionally, ensure that the reaction mixture is not too concentrated, as this can also promote elimination.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (like bromine). In this case, bromocyclohexane is a secondary alkyl halide, meaning the carbon attached to the bromine is connected to two other carbon atoms. Understanding the structure and reactivity of alkyl halides is crucial for predicting their behavior in nucleophilic substitution reactions.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like bromine in bromocyclohexane) by a nucleophile (such as hydroxide ion). The mechanism can proceed via either an SN1 or SN2 pathway, depending on the structure of the alkyl halide and the conditions. For synthesizing cyclohexanol, an SN2 mechanism is preferred to minimize the formation of cyclohexene, which occurs through elimination reactions.

Elimination vs. Substitution

In organic chemistry, elimination reactions involve the removal of a small molecule (like HBr) from a larger molecule, often leading to the formation of alkenes, such as cyclohexene. In contrast, substitution reactions replace one functional group with another. To synthesize cyclohexanol with minimal cyclohexene formation, conditions should favor substitution over elimination, such as using a lower temperature and a strong nucleophile like hydroxide ion.

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