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

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal Protecting Group

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal Protecting Group

Previous problemNext problem

3:47 minutes

Problem 51d

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
(d)

Verified step by step guidance

Step 1: Analyze the starting material and product. The starting material is a cyclopentanone with an aldehyde group (-CHO) at the 2-position. The product is a cyclopentane derivative with a hydroxyl group (-OH) and a hydrogen added to the alpha-carbon of the ketone group, indicating an aldol addition reaction.

Step 2: Identify the reaction type. This transformation involves an aldol addition reaction, where the enolate ion formed from the ketone reacts with the aldehyde group to form a β-hydroxy ketone.

Step 3: Choose the appropriate base. Use a mild base such as sodium hydroxide (NaOH) or potassium hydroxide (KOH) to generate the enolate ion from the ketone group. Ensure the reaction is carried out in an aqueous or alcoholic solvent to facilitate the aldol addition.

Step 4: Allow the enolate ion to attack the aldehyde group. The enolate ion formed from the ketone will act as a nucleophile and attack the electrophilic carbonyl carbon of the aldehyde group, forming a new C-C bond and resulting in the β-hydroxy ketone product.

Step 5: Optimize reaction conditions for good yield. Control the temperature and reaction time to prevent side reactions such as aldol condensation. Use purification techniques like recrystallization or chromatography to isolate the desired product efficiently.

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.

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions and transformations that convert starting materials into desired products. Understanding these pathways is crucial for planning efficient syntheses, as it involves selecting appropriate reagents, conditions, and reaction mechanisms to achieve high yields and minimize by-products.

Reagents and Solvents

Reagents are substances used to bring about a chemical reaction, while solvents are the mediums in which reactions occur. Choosing the right reagents and solvents is essential for optimizing reaction conditions, influencing factors such as solubility, reactivity, and selectivity, which ultimately affect the yield and efficiency of the synthetic conversion.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step sequence of elementary reactions that occur during a chemical transformation. A thorough understanding of these mechanisms allows chemists to predict the outcomes of reactions, identify potential side reactions, and design strategies to enhance product formation and yield in synthetic processes.

Watch next

Master Protecting Groups with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Predict the products formed when cyclohexanone reacts with the following reagents.

(d) ethylene glycol and p-toluenesulfonic acid

Textbook Question

Propose mechanisms for the following reactions.

(d)

Textbook Question

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(a)

Textbook Question

Predict the major products of the following reactions:

(d)

Textbook Question

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(d)

Textbook Question

One of these reacts with dilute aqueous acid and the other does not. Give a mechanism for the one that reacts, and show why this mechanism does not work for the other one.

(b)

Textbook Question

Rationalize the difference in Kₑq for the following reactions. Be sure to account for both ∆S and ∆H.

1. Analyze ∆S and ∆H differences." width="737">

Open Question

Provide the chemical steps necessary for the following synthesis.

Show more practices