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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3:06 minutes

Problem 10e,f

Textbook Question

Predict the products of the following reactions:
(e)
(f)

Verified step by step guidance

Step 1: Analyze the reagent DIBAL-H (Diisobutylaluminum hydride). DIBAL-H is a selective reducing agent that reduces esters and lactones to aldehydes under controlled conditions (low temperature, -78°C). It does not reduce the carbonyl group completely to an alcohol in this case.

Step 2: For reaction (e), identify the functional groups in the starting material. The molecule contains an ester group (O=C-OCH₃) and a double bond in the alkyl chain. DIBAL-H selectively reduces the ester group to an aldehyde without affecting the double bond.

Step 3: For reaction (f), identify the functional groups in the starting material. The molecule contains a lactone (cyclic ester). DIBAL-H selectively reduces the lactone to an aldehyde, opening the ring structure in the process.

Step 4: Consider the reaction conditions. The reaction is performed at -78°C, which ensures selective reduction to aldehydes without over-reduction to alcohols. The addition of water (H₂O) in the second step quenches the reaction and hydrolyzes the aluminum complex formed during reduction.

Step 5: Predict the products. For reaction (e), the ester group is reduced to an aldehyde, and the double bond remains intact. For reaction (f), the lactone is reduced to an aldehyde, resulting in a linear molecule with an aldehyde group at one end.

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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 they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.

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 allows chemists to predict reactivity patterns and the types of reactions that can occur, which is essential for determining the products of a given reaction.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is important for predicting the products of reactions, especially in cases where chirality or geometric isomerism plays a role. Understanding stereochemical outcomes can significantly influence the properties and reactivity of organic compounds.

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