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

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6:34 minutes

Problem 29d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the transformation. The starting material is a diketone with two methyl groups on a cyclohexane ring. The product introduces a hydroxyl group (-OH) and a hydrogen (-H) at the alpha position relative to one of the ketones. This suggests an aldol addition reaction.

Step 2: Identify the reagents needed for the aldol addition. Use a base such as NaOH or KOH to deprotonate the alpha hydrogen of one of the ketones, forming an enolate ion. The enolate will act as a nucleophile.

Step 3: Allow the enolate to attack the carbonyl carbon of the other ketone within the same molecule. This intramolecular reaction forms a new C-C bond and generates a beta-hydroxy ketone intermediate.

Step 4: Neutralize the reaction mixture to stabilize the beta-hydroxy ketone product. This step ensures the hydroxyl group remains intact and prevents further reactions such as dehydration.

Step 5: Confirm the stereochemistry of the product. The hydroxyl group and hydrogen are added to the alpha position, and the stereochemistry is determined by the reaction conditions and the structure of the starting material.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as it describes the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the types of bonds formed or broken. A clear grasp of mechanisms helps predict the outcome of reactions and the conditions required for successful synthesis.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting reactivity and understanding how different reagents will interact during a synthesis. This knowledge allows chemists to design pathways for creating desired compounds effectively.

Reagents and Conditions

The choice of reagents and reaction conditions is fundamental in organic synthesis. Different reagents can facilitate specific transformations, while conditions such as temperature, pressure, and solvent can influence reaction rates and selectivity. Understanding how to select and optimize these factors is key to successfully carrying out a synthesis and achieving the desired product.

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Related Practice

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 synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(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.

Open Question

Provide the chemical steps necessary for the following synthesis.

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