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

Intramolecular Aldol Condensation

Organic Chemistry

25. Condensation Chemistry

Intramolecular Aldol Condensation

Previous problemNext problem

2:23 minutes

Problem 33a

Textbook Question

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

(a) Show the diketone that would cyclize to give this product.

Verified step by step guidance

Step 1: Analyze the given product structure. The compound is a bicyclic ketone with a cyclohexane ring fused to a cyclopentane ring. The ketone group is located on the cyclopentane ring.

Step 2: Recall the mechanism of base-catalyzed aldol cyclization. This reaction involves the formation of a new carbon-carbon bond between two carbonyl groups, typically resulting in a cyclic structure.

Step 3: Identify the diketone precursor. To form the bicyclic structure, the diketone must have two carbonyl groups positioned such that they can undergo intramolecular aldol condensation. In this case, the precursor would be a 2-substituted cyclohexanone with a second ketone group at the appropriate position.

Step 4: Draw the diketone structure. The diketone should have one ketone group on the cyclohexane ring and another ketone group on the side chain at the position that allows cyclization to form the five-membered ring.

Step 5: Verify the connectivity. Ensure that the diketone structure aligns with the product after cyclization, considering the formation of the new bond and the elimination of water during the aldol condensation.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Aldol Condensation

Aldol condensation is a fundamental reaction in organic chemistry where an enolate ion reacts with a carbonyl compound to form a β-hydroxy aldehyde or ketone. This reaction can occur intramolecularly, leading to the formation of cyclic compounds. The process typically involves a base that deprotonates the carbon adjacent to the carbonyl, generating the enolate, which then attacks the carbonyl carbon of another molecule.

Cyclization

Cyclization refers to the process of forming a cyclic compound from a linear precursor. In the context of aldol reactions, intramolecular cyclization occurs when a diketone or a similar compound undergoes a reaction where the nucleophile and electrophile are part of the same molecule, leading to the formation of a ring structure. This is significant in synthesizing complex cyclic molecules, often seen in natural products and pharmaceuticals.

Diketones

Diketones are organic compounds containing two carbonyl groups (C=O) within the same molecule. They can serve as precursors in aldol reactions, where one carbonyl group can form an enolate and react with the other carbonyl group to create a cyclic structure. Understanding the structure and reactivity of diketones is crucial for predicting the products of aldol cyclization and for designing synthetic pathways in organic chemistry.

Watch next

Master Diketones with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Draw the product of the reaction of each of the following compounds with a base:

Textbook Question

Can 2,4-pentanedione undergo an intramolecular aldol addition? If so, why? If not, why not?

Textbook Question

Draw the product of the reaction of each of the following compounds with a base:

Textbook Question

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

(b) Propose a mechanism for the cyclization.

Textbook Question

When cyclodecane-1,6-dione is treated with sodium carbonate, the product gives a UV spectrum similar to that of 1-acetyl-2-methylcyclopentene. Propose a structure for the product, and give a mechanism for its formation.

Textbook Question

Show how octane-2,7-dione might cyclize to a cycloheptenone. Explain why ring closure to the cycloheptenone is not favored.

Textbook Question

Draw the product of the reaction of each of the following compounds with a base:

Textbook Question

Draw the product of the reaction of each of the following compounds with a base:

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.(a) Show the diketone that would cyclize to give this product.

Key Concepts

Aldol Condensation

Cyclization

Diketones

Watch next

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

(a) Show the diketone that would cyclize to give this product.