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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2:20 minutes

Problem 39b

Textbook Question

Predict the product of the following reaction sequences.
(b)

Verified step by step guidance

Step 1: Identify the functional groups present in the starting material. This will help you understand the reactivity and possible transformations that can occur during the reaction sequence.

Step 2: Analyze the reagents and conditions provided in the reaction sequence. Each reagent can perform specific transformations, such as oxidation, reduction, substitution, or elimination.

Step 3: Apply the first reagent to the starting material. Consider the mechanism of the reaction and how the reagent interacts with the functional groups present. For example, if the reagent is a strong acid, it might protonate an alcohol group.

Step 4: Proceed to the next reagent in the sequence. Use the product from the previous step as the new starting material. Again, consider the mechanism and the functional groups involved. If the reagent is a nucleophile, it might attack an electrophilic center.

Step 5: Continue through the sequence until all reagents have been applied. At each step, ensure that you are considering stereochemistry, regiochemistry, and any possible rearrangements that might occur. The final product will be the result of all these transformations.

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Key Concepts

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

Reaction Mechanism

A reaction mechanism is a step-by-step description of the pathway from reactants to products. It includes the breaking and forming of bonds, intermediates, and transition states. Understanding the mechanism helps predict the outcome of a reaction by considering the stability of intermediates and the energy changes involved.

Functional Groups

Functional groups are specific groups of atoms within molecules that have characteristic properties and reactivity. Recognizing functional groups in reactants allows chemists to predict how they will interact during a reaction. Common functional groups include alcohols, alkenes, and carbonyls, each with distinct reactivity patterns.

Regioselectivity and Stereoselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others. Stereoselectivity involves the formation of one stereoisomer over another. These concepts are crucial in predicting the major product of a reaction, especially in complex organic transformations where multiple outcomes are possible.

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Related Practice

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

(d) 1-bromoheptane

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.

(f)

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.

(c)

Textbook Question

Predict the major products of the following reactions.

(b)

Textbook Question

When the ester attacked the aluminum of DIBAl-H, why did the carbonyl oxygen attack preferentially over the alkoxy oxygen?

Textbook Question

The esters shown differ only by the alkoxy group.

(i) Predict the product(s) obtained when these react with DIBAl-H.

(ii) Based on your answer, in a sequence like this, would there ever be a need to convert from one ester to another?

(b)

Textbook Question