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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4:22 minutes

Problem 30h

Textbook Question

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
(h)

Verified step by step guidance

Step 1: Begin with cyclooctyne as the starting material. Cyclooctyne is an eight-membered ring containing a triple bond. The goal is to break the ring and elongate the carbon chain while introducing functional groups.

Step 2: Perform oxidative cleavage of the alkyne bond in cyclooctyne using a reagent like ozone (O₃) followed by reductive workup (e.g., Zn/H₂O). This will yield two molecules of octanal (CH₃(CH₂)₆CHO).

Step 3: Convert octanal into octanoic acid (CH₃(CH₂)₆COOH) by oxidation. Use an oxidizing agent such as potassium permanganate (KMnO₄) or chromium-based reagents (e.g., Jones reagent).

Step 4: Perform a second oxidative cleavage on octanoic acid using a strong oxidizing agent like KMnO₄ under acidic conditions. This will break the carbon chain into smaller fragments, yielding the desired aldehyde and carboxylic acid functional groups.

Step 5: Adjust the reaction conditions to ensure the formation of the specific compound shown in the image, which contains both aldehyde and carboxylic acid groups at the ends of a linear chain. Purify the product using techniques like distillation or recrystallization.

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Key Concepts

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

Cyclooctyne Structure and Reactivity

Cyclooctyne is a cyclic alkyne with a unique structure that influences its reactivity. Its strained ring system makes it more reactive than linear alkynes, allowing for various reactions such as cycloadditions and nucleophilic attacks. Understanding its geometry and electronic properties is crucial for predicting how it can be transformed into other compounds.

Synthetic Pathways in Organic Chemistry

Synthetic pathways refer to the series of chemical reactions used to convert one compound into another. In organic synthesis, it is essential to identify the most efficient route, considering factors like yield, selectivity, and the availability of reagents. Knowledge of functional group transformations and reaction mechanisms is vital for designing these pathways.

Functional Group Interconversion

Functional group interconversion involves transforming one functional group into another within a molecule. This concept is fundamental in organic synthesis, as it allows chemists to modify compounds to achieve desired properties or reactivity. Mastery of various reactions, such as oxidation, reduction, and substitution, is necessary for effective synthesis.

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Textbook Question

Show how you would accomplish the following synthetic conversions.

Textbook Question

Work backward to show how the cyclopropane would be synthesized from the chloroalkane shown.

Textbook Question

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

Textbook Question

Identify A–E.

Textbook Question

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material:

Textbook Question

A, a compound with molecular formula C₆H₁₀, contains three methylene units. A reacts with one equivalent of H₂ over Pd/C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration/oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C₆H₁₀O₂. Provide structures for A–F.