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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4:53 minutes

Problem 38c

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)

Verified step by step guidance

Step 1: Analyze the target molecule. The compound contains a cyclopentane ring attached to a tertiary carbon with two ethyl groups, one ethoxy group, and a vinyl group. This suggests the need for a tertiary carbon center and functional group transformations.

Step 2: Start with cyclopentanol as the base material. Convert cyclopentanol to cyclopentyl bromide using PBr₃ (phosphorus tribromide) to introduce a good leaving group for subsequent reactions.

Step 3: Perform a Grignard reaction. React cyclopentyl bromide with ethyl magnesium bromide (EtMgBr) to form a cyclopentyl-ethyl intermediate. This step introduces one ethyl group to the cyclopentane ring.

Step 4: Introduce the second ethyl group and the vinyl group. Use a Friedel-Crafts alkylation reaction with ethyl chloride and vinyl chloride in the presence of AlCl₃ as a catalyst to attach these groups to the tertiary carbon center.

Step 5: Add the ethoxy group. React the tertiary carbon intermediate with sodium ethoxide (NaOEt) in ethanol to replace the remaining hydrogen on the tertiary carbon with an ethoxy group, completing the synthesis of the target molecule.

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Key Concepts

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

Synthesis of Organic Compounds

Organic synthesis involves the construction of complex organic molecules from simpler ones. This process often requires a series of chemical reactions, utilizing various reagents and conditions to achieve the desired product. Understanding the reactivity of functional groups and the mechanisms of reactions is crucial for designing effective synthetic pathways.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the question, recognizing the functional groups present in cyclopentanol and the target compound is essential for determining the appropriate reagents and reaction conditions needed for synthesis.

Reagents and Solvents in Organic Chemistry

Reagents are substances used to cause a chemical reaction, while solvents are the mediums in which reactions occur. The choice of reagents and solvents can significantly influence the outcome of a reaction, including yield and selectivity. Familiarity with common reagents and their roles in organic transformations is vital 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.

(a)

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

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

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)

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