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

Oxidizing and Reducing Agents

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidizing and Reducing Agents

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2:26 minutes

Problem 24

Textbook Question

What are the products of the following reactions?
a.
b.
c.
d.

Verified step by step guidance

Step 1: Understand the role of H2 and Raney Ni in these reactions. Raney nickel (Ni) is a catalyst commonly used for hydrogenation reactions. It facilitates the addition of hydrogen (H2) to unsaturated bonds such as double bonds, triple bonds, nitriles, and carbonyl groups.

Step 2: For reaction (a), identify the functional group in the starting material. If the starting material contains a double or triple bond, Raney Ni will catalyze the hydrogenation, converting it to a single bond. For example, an alkene (C=C) will be reduced to an alkane (C-C).

Step 3: For reaction (b), CH3CH2CH2C≡N, recognize that the nitrile group (C≡N) undergoes hydrogenation in the presence of H2 and Raney Ni. This reaction converts the nitrile group into a primary amine (-CH2NH2).

Step 4: For reaction (c), analyze the starting material. If it contains a functional group such as a carbonyl (C=O) or an unsaturated bond, Raney Ni will catalyze its reduction. For example, a ketone (C=O) will be reduced to an alcohol (-CH2OH).

Step 5: For reaction (d), CH3(C=O)OCH3, identify the ester functional group. Under hydrogenation conditions with Raney Ni, the ester can be reduced to an alcohol. Specifically, the ester bond (C=O and C-O) will break, forming two alcohols: one from the carbonyl group and one from the alkoxy group.

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Key Concepts

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

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to unsaturated organic compounds, typically alkenes or alkynes, to convert them into saturated hydrocarbons. This process is often facilitated by catalysts such as Raney nickel, which enhances the reaction rate and selectivity. Understanding hydrogenation is crucial for predicting the products of reactions involving unsaturated substrates.

Raney Nickel Catalyst

Raney nickel is a finely divided nickel-aluminum alloy that serves as a highly effective catalyst for hydrogenation reactions. It is particularly useful in reducing carbon-carbon double and triple bonds, as well as in the hydrogenation of functional groups like nitriles and carbonyls. Familiarity with the properties and applications of Raney nickel is essential for understanding its role in the reactions presented.

Functional Group Transformations

Functional group transformations refer to the chemical reactions that convert one functional group into another, altering the reactivity and properties of organic molecules. In the context of the given reactions, recognizing how hydrogenation affects various functional groups, such as nitriles and esters, is vital for predicting the final products. This concept is foundational in organic synthesis and reaction mechanisms.

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