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

DIBAL

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

DIBAL

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2:17 minutes

Problem 8e

Textbook Question

Predict the products of the following reactions.
(e) product of (c) + DIBAL-H, then hydrolysis

Verified step by step guidance

Step 1: Understand the reaction components. DIBAL-H (Diisobutylaluminum hydride) is a selective reducing agent commonly used in organic chemistry to reduce esters, nitriles, and other carbonyl compounds to aldehydes under controlled conditions. Hydrolysis typically follows the reduction step to complete the reaction.

Step 2: Analyze the product of reaction (c). Identify the functional group(s) present in the compound obtained from reaction (c). This will help determine how DIBAL-H will interact with the molecule.

Step 3: Apply the action of DIBAL-H. If the product of (c) contains an ester group, DIBAL-H will reduce it to an aldehyde. If it contains a nitrile group, DIBAL-H will reduce it to an imine intermediate, which upon hydrolysis will yield an aldehyde. Write the intermediate structure after the reduction step.

Step 4: Perform hydrolysis. After the reduction by DIBAL-H, hydrolysis (typically with water or a dilute acid) will convert any intermediate species (e.g., imines) into the final aldehyde product. Write the structure of the final product after hydrolysis.

Step 5: Verify the product. Ensure that the final product is consistent with the expected reactivity of DIBAL-H and hydrolysis. Double-check the functional groups and connectivity in the molecule to confirm the structure of the product.

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Key Concepts

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

DIBAL-H (Diisobutylaluminum Hydride)

DIBAL-H is a strong reducing agent commonly used in organic chemistry to selectively reduce esters and nitriles to aldehydes. Its ability to provide controlled reduction makes it valuable in synthetic pathways, particularly when a complete reduction to alcohol is not desired. Understanding its reactivity and mechanism is crucial for predicting the products of reactions involving carbonyl compounds.

Hydrolysis

Hydrolysis is a chemical reaction involving the breakdown of a compound due to reaction with water. In organic chemistry, hydrolysis often refers to the conversion of esters or amides into their corresponding acids and alcohols or amines, respectively. This process is essential for understanding how the products of reductions, such as those involving DIBAL-H, can be further transformed in aqueous conditions.

Product Prediction in Organic Reactions

Predicting the products of organic reactions involves understanding the functional groups present, the reagents used, and the reaction conditions. This requires knowledge of reaction mechanisms, such as nucleophilic attack and electrophilic addition, which dictate how reactants interact and transform. Mastery of these principles allows chemists to anticipate the outcome of complex reactions, such as those involving DIBAL-H and subsequent hydrolysis.

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