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

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

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5:18 minutes

Problem 60c

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:
c.

Verified step by step guidance

Step 1: Begin with cyclohexanone as your starting material. Cyclohexanone is a six-membered ring with a ketone functional group. The goal is to transform this structure into the desired compound.

Step 2: Identify the functional groups and structural changes needed to convert cyclohexanone into the target compound. This may involve adding or modifying functional groups such as alcohols, halides, or alkenes.

Step 3: Consider the reagents and conditions required for each transformation. For example, if you need to reduce the ketone to an alcohol, you might use a reducing agent like sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄).

Step 4: Plan the sequence of reactions. Determine the order in which the transformations should occur to efficiently reach the target compound. This may involve protecting groups or intermediate steps to ensure selectivity and yield.

Step 5: Execute the synthesis by performing each reaction step-by-step, monitoring the progress with techniques such as TLC (Thin Layer Chromatography) or NMR (Nuclear Magnetic Resonance) to ensure the desired transformations are occurring.

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Key Concepts

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

Cyclohexanone Structure and Reactivity

Cyclohexanone is a six-membered cyclic ketone with a carbonyl group (C=O) that significantly influences its reactivity. The carbonyl carbon is electrophilic, making it susceptible to nucleophilic attack, which is a key feature in various organic reactions. Understanding its structure helps in predicting the types of reactions it can undergo, such as nucleophilic addition or oxidation.

Synthetic Pathways in Organic Chemistry

Synthetic pathways refer to the series of chemical reactions that transform a starting material into a desired product. In organic chemistry, these pathways often involve functional group transformations, rearrangements, and the use of reagents to achieve specific modifications. Familiarity with common synthetic strategies, such as reduction, oxidation, and substitution, is essential for designing a synthesis from cyclohexanone.

Functional Group Interconversion

Functional group interconversion is a fundamental concept in organic synthesis that involves changing one functional group into another. This process is crucial when synthesizing complex molecules, as it allows chemists to modify the reactivity and properties of compounds. For example, converting a ketone like cyclohexanone into an alcohol or an alkene can open pathways to various target compounds.

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Related Practice

Textbook Question

A graduate student attempted the following reaction and did not isolate the expected product.

(a) What product did they isolate?

(b) What reagent should they have used instead to get their desired product?

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(f)

Textbook Question

Suggest a reagent for the transformation of a 1° alcohol to a 1° alkyl halide.

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(e)

Textbook Question

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH₃)₃ as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Textbook Question

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(d) concentrated HBr

(e) TsCl/pyridine, then NaBr

Textbook Question

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.

(g)

Textbook Question

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(a) PBr₃

(b) SOCl₂

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