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

25. Condensation Chemistry

Conjugate Addition

Organic Chemistry

25. Condensation Chemistry

Conjugate Addition

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8:20 minutes

Problem 73

Textbook Question

Show how the following compound can be prepared from starting materials that have no more than five carbons:

Verified step by step guidance

Step 1: Analyze the target compound. The structure contains a bicyclic ketone with two carbonyl groups. The compound has a total of 10 carbons, and the synthesis must start from materials with no more than five carbons.

Step 2: Identify key transformations. The compound can be synthesized using an aldol condensation reaction to form the bicyclic structure. This involves forming a new carbon-carbon bond between two smaller molecules.

Step 3: Select starting materials. Choose two molecules with no more than five carbons each that can undergo aldol condensation. For example, cyclopentanone (a five-carbon ketone) and acetaldehyde (a two-carbon aldehyde) can be used.

Step 4: Perform the aldol condensation. Under basic conditions, cyclopentanone can act as the nucleophile, and acetaldehyde can act as the electrophile. The enolate ion of cyclopentanone attacks the carbonyl carbon of acetaldehyde, forming a β-hydroxyketone intermediate.

Step 5: Complete the synthesis. Dehydrate the β-hydroxyketone intermediate to form the α,β-unsaturated ketone. Then, perform an intramolecular aldol condensation to form the bicyclic structure. Finally, oxidize the secondary alcohol to form the second ketone group.

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Key Concepts

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

Conjugate Addition

Conjugate addition refers to the addition of a nucleophile to an α,β-unsaturated carbonyl compound. This reaction typically involves the nucleophile attacking the β-carbon, leading to the formation of a new bond. Understanding this mechanism is crucial for synthesizing compounds from simpler starting materials, as it allows for the construction of complex structures through strategic bond formation.

Retrosynthetic Analysis

Retrosynthetic analysis is a problem-solving technique used in organic chemistry to deconstruct a target molecule into simpler precursor structures. By identifying key functional groups and potential reaction pathways, chemists can work backward from the desired compound to determine feasible starting materials. This approach is essential for planning synthetic routes that adhere to the constraint of using starting materials with no more than five carbons.

Functional Group Interconversion

Functional group interconversion involves transforming one functional group into another through chemical reactions. This concept is vital for organic synthesis, as it allows chemists to modify starting materials to create desired intermediates or final products. Recognizing how to manipulate functional groups effectively is key to achieving the target compound from simpler carbon-based precursors.

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