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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8:43 minutes

Problem 118b

Textbook Question

How could you prepare the following compounds from the given starting materials?
b.

Verified step by step guidance

Identify the starting material and the target compound. The starting material is a dichloroalkane, and the target compound is a cyclohexane derivative with three methyl groups.

Recognize that the transformation involves forming a six-membered ring. This suggests a cyclization reaction, likely through an intramolecular nucleophilic substitution.

Consider the mechanism: the chlorine atoms in the starting material can act as leaving groups. A base can be used to deprotonate one of the carbon atoms adjacent to a chlorine, forming a carbanion.

The carbanion can then perform a nucleophilic attack on the other carbon bearing a chlorine atom, leading to the formation of a cyclohexane ring and the elimination of a chloride ion.

Ensure that the reaction conditions are suitable for promoting cyclization, such as using a strong base like sodium ethoxide (NaOEt) in an appropriate solvent to facilitate the intramolecular reaction.

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Key Concepts

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

Diels-Alder Reaction

The Diels-Alder reaction is a [4+2] cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. This reaction is a key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity and ability to form new carbon-carbon bonds.

Retrosynthetic Analysis

Retrosynthetic analysis is a problem-solving technique used in organic chemistry to deconstruct complex molecules into simpler starting materials. By working backward from the target compound, chemists can identify potential synthetic routes and the necessary reactions, facilitating the design of a synthesis plan.

Reactivity of Halogenated Compounds

Halogenated compounds, such as those containing chlorine, are often more reactive than their non-halogenated counterparts due to the presence of electronegative halogen atoms. These compounds can participate in various reactions, including nucleophilic substitutions and eliminations, which are crucial for forming the diene or dienophile in a Diels-Alder reaction.

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