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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3:30 minutes

Problem 52f

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
f. 1-(phenylmethyl)cyclohexanol

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. Perform a hydroboration-oxidation reaction to convert the alkene into an alcohol. Use BH₃·THF (borane-tetrahydrofuran complex) followed by H₂O₂ (hydrogen peroxide) and NaOH (sodium hydroxide) to yield cyclohexanol.

Step 2: Prepare benzyl bromide (C₆H₅CH₂Br) as the source of the phenylmethyl group. Benzyl bromide can be obtained by reacting toluene (C₆H₅CH₃) with bromine (Br₂) in the presence of light or a radical initiator.

Step 3: Perform a Williamson ether synthesis to attach the phenylmethyl group to cyclohexanol. First, convert cyclohexanol into cyclohexoxide by treating it with a strong base such as NaH (sodium hydride). Then, react cyclohexoxide with benzyl bromide to form 1-(phenylmethyl)cyclohexanol.

Step 4: Ensure stereochemical control during the synthesis, as the reaction may produce a mixture of stereoisomers. If necessary, use purification techniques such as recrystallization or chromatography to isolate the desired product.

Step 5: Verify the structure of the final product, 1-(phenylmethyl)cyclohexanol, using spectroscopic methods such as NMR (nuclear magnetic resonance) and IR (infrared spectroscopy) to confirm the presence of the phenylmethyl group and hydroxyl functionality.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic compounds from simpler ones through a series of chemical reactions. Understanding the synthesis pathway is crucial for determining the necessary reagents and conditions required to achieve the desired product. This involves knowledge of functional group transformations, reaction mechanisms, and the reactivity of different organic compounds.

Reagents and Reaction Mechanisms

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Each reagent can influence the reaction pathway and the final structure of the compound. Familiarity with common reagents and their mechanisms—such as nucleophilic substitutions, electrophilic additions, and reductions—is essential for planning a successful synthesis.

Functional Groups and Their Transformations

Functional groups are specific groups of atoms within molecules that determine the chemical properties and reactions of those molecules. In the synthesis of 1-(phenylmethyl)cyclohexanol, recognizing the functional groups present in methylenecyclohexane and the target compound is vital. This knowledge allows chemists to identify appropriate reactions that can introduce or modify these functional groups to achieve the desired compound.

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