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

16. Conjugated Systems

Diels-Alder Retrosynthesis

Organic Chemistry

16. Conjugated Systems

Diels-Alder Retrosynthesis

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7:16 minutes

Problem 87

Textbook Question

How could you synthesize the following compound from starting materials containing no more than six carbons?

Verified step by step guidance

Step 1: Analyze the target molecule. The compound contains two ketone groups separated by a chain of four carbons. This suggests that the synthesis might involve a reaction that forms ketones, such as oxidation or acylation.

Step 2: Plan the synthesis. Since the starting materials are limited to six carbons, consider using smaller carbon fragments and coupling them together. A possible approach is to use a Claisen condensation, which can form a β-diketone from two esters or ketones.

Step 3: Select appropriate starting materials. Choose two compounds with no more than six carbons that can undergo Claisen condensation. For example, ethyl acetate (CH₃COOCH₂CH₃) and butanone (CH₃CH₂COCH₃) could be suitable starting materials.

Step 4: Perform the Claisen condensation. Treat the selected starting materials with a strong base, such as sodium ethoxide (NaOEt), to deprotonate the α-hydrogen of one molecule and allow it to attack the carbonyl carbon of the other molecule. This forms a β-diketone intermediate.

Step 5: Purify and verify the product. After the reaction, isolate the product using techniques like distillation or recrystallization. Confirm the structure of the synthesized compound using spectroscopic methods such as NMR or IR.

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Key Concepts

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

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding the functional groups present in the target compound is essential for determining the appropriate synthetic pathways and reactions needed to construct the compound from simpler starting materials.

Retrosynthetic Analysis

Retrosynthetic analysis is a strategy used in organic chemistry to deconstruct a target molecule into simpler precursor structures. By working backward from the desired compound, chemists can identify feasible synthetic routes and the necessary starting materials, which is crucial for planning the synthesis of the compound in question.

Reagents and Reaction Conditions

Different chemical reactions require specific reagents and conditions to proceed effectively. Knowledge of common reagents, such as acids, bases, and catalysts, as well as the conditions under which reactions occur (temperature, pressure, solvent), is vital for successfully synthesizing the target compound from the chosen starting materials.

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