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1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

16. Carboxylic Acids and Their Derivatives

Amide Formation

16. Carboxylic Acids and Their Derivatives

Amide Formation: Videos & Practice Problems

Video Lessons Practice Worksheet

Topic summary

Amide formation occurs through a condensation reaction between a carboxylic acid and an amine, resulting in the loss of water. The carboxylic acid donates a hydroxyl group, while the amine contributes a hydrogen atom from its nitrogen. An H⁺ catalyst initiates the reaction, allowing the carbon and nitrogen to bond, forming an amide, characterized by a carbonyl group connected to a nitrogen. This process is essential in organic chemistry, highlighting the significance of functional groups like amines and carboxylic acids in synthesizing complex molecules.

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Amide Formation Concept 1

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Amide Formation Concept 1 Video Summary

Amide formation is a significant chemical reaction where a carboxylic acid reacts with an amine through a condensation process to produce an amide. In this reaction, water is eliminated, which is a hallmark of condensation reactions. Specifically, the hydroxyl group (–OH) from the carboxylic acid and one hydrogen atom from the amine's nitrogen are removed, resulting in the formation of water.

For the reaction to proceed, the nitrogen atom in the amine must have at least one hydrogen atom available. Additionally, an acid catalyst (H⁺) is often required to initiate the reaction, facilitating the process.

The general reaction can be represented as follows: a carboxylic acid, denoted as RCOOH, reacts with an amine, R'NH₂. During the reaction, the –OH from the carboxylic acid and an H from the amine are lost, forming water (H₂O). The carbon atom from the carboxylic acid and the nitrogen atom from the amine then form a new bond, resulting in the creation of an amide, which is characterized by a carbonyl group (C=O) bonded to a nitrogen atom (–NH₂).

In summary, the formation of an amide through the condensation of a carboxylic acid and an amine is a crucial reaction in organic chemistry, highlighting the interplay between functional groups and the importance of catalysts in facilitating chemical transformations.

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Amide Formation Example 1

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Amide Formation Example 1 Video Summary

When 4-methylpentanoic acid reacts with butylamine, an amide product is formed through a condensation reaction. In this process, the hydroxyl group (–OH) from the carboxylic acid and a hydrogen atom (–H) from the amine are eliminated, resulting in the formation of the amide bond.

The structure of 4-methylpentanoic acid can be represented as follows:

4-methylpentanoic acid structure

In the reaction, the carbonyl group (C=O) of the carboxylic acid remains intact, while the nitrogen atom of butylamine forms a bond with the carbon of the carbonyl group. The nitrogen loses one hydrogen atom but retains another, which is still connected to the butyl chain. The resulting amide product can be depicted as:

Amide product structure

Thus, the final amide product is characterized by the presence of the carbonyl group adjacent to the nitrogen atom, which is also bonded to the butyl group. This reaction exemplifies the formation of an amide through the condensation of a carboxylic acid and an amine, highlighting the importance of functional group transformations in organic chemistry.

Problem

Predict the amide product formed when 2,2-dimethylpropanoic acid reacts with dimethylamine.

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Here’s what students ask on this topic:

What is the mechanism of amide formation from carboxylic acids and amines?

Amide formation from carboxylic acids and amines involves a condensation reaction. The carboxylic acid donates a hydroxyl group (OH), and the amine donates a hydrogen atom (H) from its nitrogen. An H⁺ catalyst initiates the reaction. The OH and H combine to form water (H₂O), which is lost in the process. The carbon from the carboxylic acid and the nitrogen from the amine then bond to form an amide, characterized by a carbonyl group (C=O) connected to a nitrogen (N). This reaction is crucial in organic chemistry for synthesizing complex molecules.

Why is an H⁺ catalyst necessary in amide formation?

An H⁺ catalyst is necessary in amide formation because it helps to activate the carboxylic acid and the amine, making them more reactive. The H⁺ protonates the carbonyl oxygen of the carboxylic acid, increasing its electrophilicity. This makes it easier for the amine to attack the carbonyl carbon, facilitating the formation of the amide bond. Without the H⁺ catalyst, the reaction would proceed much more slowly or might not occur at all under standard conditions.

What are the products of the condensation reaction between a carboxylic acid and an amine?

The products of the condensation reaction between a carboxylic acid and an amine are an amide and water. The carboxylic acid loses its hydroxyl group (OH), and the amine loses a hydrogen atom (H) from its nitrogen. These combine to form water (H₂O). The remaining carbon from the carboxylic acid and nitrogen from the amine bond to form the amide, which is characterized by a carbonyl group (C=O) connected to a nitrogen (N).

What is the role of the hydroxyl group in amide formation?

The hydroxyl group (OH) in the carboxylic acid plays a crucial role in amide formation. During the condensation reaction, the hydroxyl group is lost from the carboxylic acid, combining with a hydrogen atom (H) from the amine to form water (H₂O). This loss of water is essential for the formation of the amide bond, where the carbon from the carboxylic acid bonds with the nitrogen from the amine, resulting in the creation of an amide.

How does the structure of an amide differ from that of a carboxylic acid?

The structure of an amide differs from that of a carboxylic acid primarily in the functional groups attached to the carbonyl carbon. In a carboxylic acid, the carbonyl carbon is bonded to a hydroxyl group (OH), forming the carboxyl group (COOH). In an amide, the carbonyl carbon is bonded to a nitrogen atom (N), forming the amide group (CONH₂). This difference in functional groups results in distinct chemical properties and reactivity for amides compared to carboxylic acids.