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

Aldol Condensation

Organic Chemistry

25. Condensation Chemistry

Aldol Condensation

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3:07 minutes

Problem 32b

Textbook Question

Show how each compound can be dissected into reagents joined by an aldol condensation, then decide whether the necessary aldol condensation is feasible.
(b)

Verified step by step guidance

Step 1: Analyze the given compound structure. The compound contains a β-hydroxy ketone functional group, which is characteristic of an aldol addition product. This suggests that the compound was formed via an aldol condensation reaction.

Step 2: Identify the two fragments that could have combined during the aldol condensation. The β-hydroxy ketone structure indicates that one fragment must be an aldehyde or ketone with an α-hydrogen, and the other fragment must also be an aldehyde or ketone.

Step 3: Break the compound at the β-hydroxy position to determine the two possible starting reagents. The hydroxyl group and the adjacent carbonyl group suggest that the compound can be dissected into two phenyl-substituted ketones or aldehydes.

Step 4: Verify the feasibility of the aldol condensation. Check if both fragments have α-hydrogens to enable enolate formation. In this case, both fragments (e.g., acetophenone derivatives) have α-hydrogens, making the aldol condensation feasible.

Step 5: Consider the stereochemistry and substitution pattern. The presence of the hydroxyl group and the methyl and ethyl substituents suggests that the reaction conditions favored the formation of this specific β-hydroxy ketone product. Ensure that the reaction mechanism aligns with the observed structure.

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Key Concepts

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

Aldol Condensation

Aldol condensation is a reaction between aldehydes or ketones that contain alpha-hydrogens, leading to the formation of β-hydroxy aldehydes or ketones. This reaction involves the nucleophilic addition of an enolate ion to a carbonyl compound, followed by dehydration to yield an α,β-unsaturated carbonyl compound. Understanding this process is crucial for dissecting compounds into their respective reagents.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of aldol condensation, hydroxyl (-OH) and carbonyl (C=O) groups are particularly important, as they dictate the reactivity and the pathways available for the reaction. Recognizing these groups in the given compounds is essential for determining the feasibility of the aldol condensation.

Feasibility of Reactions

The feasibility of a chemical reaction refers to whether the reaction can occur under given conditions, often assessed through thermodynamic and kinetic considerations. In aldol condensation, factors such as the stability of the resulting product, steric hindrance, and the presence of suitable functional groups influence whether the reaction will proceed. Evaluating these aspects is key to determining if the aldol condensation is viable for the compounds in question.

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Related Practice

Textbook Question

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(a)

Textbook Question

Propose a mechanism for the dehydration of diacetone alcohol to mesityl oxide

(a) in acid.

(b) in base.

Textbook Question

Show how each compound can be dissected into reagents joined by an aldol condensation, then decide whether the necessary aldol condensation is feasible.

(a)

Textbook Question

Using cyclopentanone as the reactant, show the product of

b. an aldol addition.

c. an aldol condensation.

Textbook Question

Show how each compound can be dissected into reagents joined by an aldol condensation, then decide whether the necessary aldol condensation is feasible.

(c)

Textbook Question

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

(d)

Textbook Question

(e)

Textbook Question

(f)

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