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

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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3:01 minutes

Problem 60a,b

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the target compounds. The first compound is cyclohexanol, which is an alcohol derived from cyclohexanone. The second compound is cyclohexene, which is an alkene derived from cyclohexanone.

Step 2: For the synthesis of cyclohexanol (compound a), perform a reduction reaction. Cyclohexanone can be reduced to cyclohexanol using a reducing agent such as sodium borohydride (NaBH₄) or lithium aluminum hydride (LiAlH₄). The reaction involves the addition of hydrogen to the carbonyl group of cyclohexanone.

Step 3: Write the chemical equation for the reduction of cyclohexanone to cyclohexanol:

C ₆ H ₁₀ O + H ₂ \to C ₆ H ₁₂ O

Step 4: For the synthesis of cyclohexene (compound b), perform a dehydration reaction. Cyclohexanol can be dehydrated to cyclohexene using an acid catalyst such as concentrated sulfuric acid (H₂SO₄) or phosphoric acid (H₃PO₄). The reaction involves the elimination of water from cyclohexanol.

Step 5: Write the chemical equation for the dehydration of cyclohexanol to cyclohexene:

C ₆ H ₁₂ O \to C ₆ H ₁₀ + H ₂ O

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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 essential for various synthetic transformations. 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 crucial for designing the synthesis of complex molecules from simpler precursors.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions is critical in organic synthesis, as they determine the efficiency and selectivity of the reactions. Different reagents can facilitate specific transformations, such as Grignard reagents for nucleophilic additions or oxidizing agents for functional group conversions. Understanding how to select appropriate reagents and optimize conditions, such as temperature and solvent, is essential for successful synthesis.

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Related Practice

Textbook Question

Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways.

(b)

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 2:

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(a) trans-cyclopentane-1,2-diol

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(c)

Textbook Question

Give the structures of the intermediates represented by letters J, L, M, and N in this synthesis.

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 1:

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.

(a)

(b)

(c)

Textbook Question

Determine the structures of compounds A through G, including stereochemistry where appropriate.

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