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

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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5:53 minutes

Problem 55b

Textbook Question

Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.
(b)

Verified step by step guidance

Identify the target ketone structure. A ketone has the general formula \( R_2C=O \), where \( R \) represents alkyl or aryl groups.

Recognize that nitriles can be converted to ketones using organometallic reagents. The general reaction involves the addition of an organometallic reagent to a nitrile, followed by hydrolysis.

Consider the structure of the ketone you want to synthesize. Determine the two possible alkyl or aryl groups \( R \) that could be attached to the carbonyl carbon.

Select a nitrile that corresponds to one of the \( R \) groups. The nitrile should have the formula \( R-C\equiv N \).

Choose an organometallic reagent that corresponds to the other \( R \) group. Common choices include Grignard reagents \( R-MgX \) or organolithium reagents \( R-Li \).

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Key Concepts

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

Nitrile Chemistry

Nitriles are organic compounds containing a cyano group (-C≡N) attached to a carbon atom. They are versatile intermediates in organic synthesis, often used to form ketones through reactions with organometallic reagents. Understanding the reactivity and transformation of nitriles is crucial for predicting the outcome of such reactions.

Organometallic Reagents

Organometallic reagents, such as Grignard reagents (RMgX) and organolithium compounds (RLi), are pivotal in organic synthesis for forming carbon-carbon bonds. These reagents react with nitriles to form ketones by adding the organic group to the carbon of the cyano group, followed by hydrolysis. Mastery of their reactivity and selectivity is essential for successful ketone synthesis.

Ketone Formation

Ketones are carbonyl compounds characterized by a carbon atom double-bonded to an oxygen atom and two alkyl or aryl groups. In organic synthesis, ketones can be formed by reacting nitriles with organometallic reagents, which adds an organic group to the nitrile, followed by hydrolysis. Understanding the mechanisms and conditions for ketone formation is key to designing effective synthetic routes.

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