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9.6.3 - Acylation

Interactive Audio Lesson

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Introduction to Amines

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Teacher
Teacher

Today we're going to learn about amines, which are derivatives of ammonia. Can anyone tell me how amines are formed?

Student 1
Student 1

Amines are formed by replacing hydrogen atoms in ammonia with alkyl or aryl groups.

Teacher
Teacher

Exactly! Amines can be classified as primary, secondary, or tertiary based on how many hydrogen atoms are replaced. Can anyone give me an example of each?

Student 2
Student 2

For primary, I think it's methylamine, for secondary it could be dimethylamine, and for tertiary, trimethylamine.

Teacher
Teacher

Great job! Remembering the classification is key. Let's use the acronym 'PST' for Primary, Secondary, Tertiary as a memory aid.

Student 3
Student 3

That's helpful!

Teacher
Teacher

In summary, amines are crucial in organic chemistry and we'll delve into their use in synthesis and applications shortly.

Amines Nomenclature and Structure

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Teacher
Teacher

Let's talk about how to name amines. What do you recall about their nomenclature?

Student 4
Student 4

We name them by either the common names, like methylamine or through the IUPAC system like methanamine.

Teacher
Teacher

Correct! And remember to specify the position of amino groups when there are multiple on a carbon chain. Can someone explain why this is important?

Student 2
Student 2

It's important because it gives us different isomers which can have distinct properties.

Teacher
Teacher

Exactly! This highlights why understanding nomenclature is essential in organic chemistry. Let's practice some examples together.

Methods of Preparation of Amines

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Teacher
Teacher

Now, let's discuss methods to prepare amines. What methods can you recall?

Student 1
Student 1

We can reduce nitro compounds to get amines or use ammonolysis of alkyl halides.

Teacher
Teacher

Great! Reduction is one method, and ammonolysis is another. Can anyone explain the Gabriel synthesis?

Student 4
Student 4

Gabriel synthesis involves using phthalimide to create primary amines, right?

Teacher
Teacher

Yes, that's correct! Let's remember this with the mnemonic 'G for Gabriel, P for Phthalimide.' To prepare primary amines effectively, Gabriel is the way!

Physical Properties and Basicity of Amines

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Teacher
Teacher

Next, let’s analyze the physical properties of amines. Who can tell me about the solubility and boiling points of these compounds?

Student 3
Student 3

Lower amines are often gases and are soluble in water, while larger amines are liquids or solids with lower solubility.

Teacher
Teacher

Exactly, and this is due to hydrogen bonding! As for boiling points, what trend do we observe?

Student 2
Student 2

Primary amines have higher boiling points than secondary, which are higher than tertiary!

Teacher
Teacher

Perfect! Let's use the acronym 'PST' again coupled with 'Higher to Lower'. This is essential in understanding their structures.

Chemical Reactions of Amines

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Teacher
Teacher

Finally, let’s look at how amines react. What happens when they encounter acids?

Student 4
Student 4

They react to form salts!

Teacher
Teacher

Yes! Furthermore, what about their behavior with nitrous acid?

Student 1
Student 1

They form diazonium salts!

Teacher
Teacher

Exactly! And these reactions are significant in synthesis especially in the creation of dyes. Remember: 'Amines to Salts, then to Diazonium!'

Student 3
Student 3

That’s really helpful for remembering the sequence!

Introduction & Overview

Read a summary of the section's main ideas. Choose from Basic, Medium, or Detailed.

Quick Overview

This section outlines the characteristics, classifications, and synthesis of amines, focusing on their roles in organic chemistry.

Standard

Amines are classified as derivatives of ammonia, with primary, secondary, and tertiary types based on the number of hydrogen atoms replaced with alkyl or aryl groups. The section discusses the structure, nomenclature, preparation methods, physical properties, and chemical behavior of amines, emphasizing their applications in medicine and dyes.

Detailed

Acylation of Amines

Amines are organic compounds derived from ammonia through the substitution of one or more hydrogen atoms by alkyl or aryl groups. This section delineates their structure, classification into primary, secondary, and tertiary types, and methods of nomenclature using common names and IUPAC conventions. Amines can be synthesized through several chemical pathways such as the reduction of nitro compounds, ammonolysis of alkyl halides, and Gabriel synthesis.

Key Aspects of Amines

  1. Structure and Classification: Amines adopt a pyramidal structure, with nitrogen in sp3 hybridization. They are classified:
  2. Primary (1°): One hydrogen replaced
  3. Secondary (2°): Two hydrogens replaced
  4. Tertiary (3°): All three hydrogens replaced.
  5. Nomenclature: Comprised of both common names (e.g., methylamine) and systematic IUPAC names (e.g., methanamine).
  6. Preparation: Includes reduction of nitro compounds, ammonolysis of halides, and specialized syntheses like the Gabriel phthalimide synthesis and Hoffmann bromamide degradation.
  7. Properties: Amines exhibit basicity, solubility in water (primarily for primary amines), and experience significant hydrogen bonding resultant from the nitrogen's lone pair of electrons.
  8. Reactions: Identifies how amines interact with acids to form salts, and their behavior with various reagents like nitrous acid and carbylamine.
  9. Diazonium Salts: Produced from primary aromatic amines, diazonium salts are important for further syntheses, including azo dye formation.

This section establishes the foundational knowledge necessary to understand how amines function in organic chemistry and their extensive utility in pharmaceutical and industrial applications.

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Audio Book

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Overview of Acylation

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Aliphatic and aromatic primary and secondary amines react with acid chlorides, anhydrides and esters by nucleophilic substitution reaction. This reaction is known as acylation. You can consider this reaction as the replacement of hydrogen atom of –NH2 or >N–H group by the acyl group.

Detailed Explanation

Acylation is a chemical reaction where an acyl group is introduced into a molecule. In this case, we focus on how amines (which are nitrogen-containing compounds) react with different acylating agents like acid chlorides or anhydrides. During this reaction, the hydrogen atoms attached to the amine's nitrogen (–NH2 or >N–H) are replaced with an acyl group (RCO–). This process is called nucleophilic substitution because the amine acts as a nucleophile, attacking the acyl component. As a result, the product formed is known as an amide.

Examples & Analogies

Think of acylation like replacing a light bulb in your house. When you replace the bulb (the hydrogen atom), you’re not just removing it; you are installing a new one that serves a different purpose (the acyl group). Just as a new light bulb enhances the room's functionality, adding an acyl group to the amine changes its properties and usefulness, transforming it into an amide, which has different chemical characteristics.

Reaction Example

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The products obtained by acylation reaction are known as amides. The reaction is carried out in the presence of a base stronger than the amine, like pyridine, which removes HCl so formed and shifts the equilibrium to the right hand side.

Detailed Explanation

When amines undergo acylation, they form amides as the final products. This reaction is typically facilitated by the presence of a base, such as pyridine, which helps to neutralize the hydrochloric acid (HCl) that forms during the reaction. By removing this acid from the reaction mixture, the equilibrium is driven forward, increasing the amount of product (amide) formed. This step is crucial because it ensures that the reaction proceeds efficiently, leading to a higher yield of the desired amide.

Examples & Analogies

Imagine you’re baking a cake, and you accidentally add too much salt (acting like HCl in the reaction). If there’s someone to taste and remove excess salt while you bake (similar to how pyridine neutralizes HCl), your cake ends up tasting much better! This analogy demonstrates how removing unwanted by-products allows more of the good stuff (the amide) to form.

Special Case: Benzoylation

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Amines also react with benzoyl chloride (C6H5COCl). This reaction is known as benzoylation.

Detailed Explanation

Benzoylation is a specific case of acylation where an amine reacts with benzoyl chloride. In this reaction, the benzoyl chloride acts similarly to other acid chlorides, introducing the benzoyl group (C6H5CO–) into the amine. The product formed is a benzamide, which incorporates the characteristics of both the amine and the benzoyl group. This reaction is significant because it highlights how the structure of the acyl group can influence the reactivity and properties of the resulting molecule.

Examples & Analogies

You can think of benzoylation like adding a flavor to your ice cream. If plain vanilla ice cream represents the amine, adding chocolate syrup (benzoyl chloride) transforms it into a chocolate-flavored treat (benzamide). The new flavor not only changes the taste but also enhances the overall experience of eating the ice cream, just like how the benzoyl group alters the properties of the amide.

Definitions & Key Concepts

Learn essential terms and foundational ideas that form the basis of the topic.

Key Concepts

  • Amines: Derived from ammonia with H replaced by alkyl/aryl.

  • Classification: Primary, secondary, and tertiary based on hydrogen replacement.

  • Nomenclature: Common and IUPAC naming methods.

  • Preparation Methods: Reduction, ammonolysis, Gabriel synthesis.

  • Properties: Basicity, solubility, boiling points affected by hydrogen bonding.

  • Diazonium Salts: Formed from amines, crucial for organic synthesis.

Examples & Real-Life Applications

See how the concepts apply in real-world scenarios to understand their practical implications.

Examples

  • Methylamine as an example of a primary amine.

  • Dimethylamine as an example of a secondary amine.

  • Trimethylamine as an example of a tertiary amine.

  • Gabriel synthesis example to create a primary amine.

Memory Aids

Use mnemonics, acronyms, or visual cues to help remember key information more easily.

🎯 Super Acronyms

Use 'PST' to remember Primary, Secondary, Tertiary for amines.

🧠 Other Memory Gems

  • For amine preparation: 'Re-A-G' for Reduction, Ammonolysis, Gabriel synthesis.

🎵 Rhymes Time

  • Primary amine's the first you see, secondary's two, and three is free!

📖 Fascinating Stories

  • Imagine a family of amines. The primary amine is the oldest child, surrounded by younger siblings representing secondary and tertiary amines.

Flash Cards

Review key concepts with flashcards.

Glossary of Terms

Review the Definitions for terms.

  • Term: Amines

    Definition:

    Organic compounds derived from ammonia with one or more hydrogen atoms replaced by alkyl or aryl groups.

  • Term: Primary Amines

    Definition:

    Amines with one alkyl or aryl group attached to the nitrogen.

  • Term: Secondary Amines

    Definition:

    Amines with two alkyl or aryl groups attached to the nitrogen.

  • Term: Tertiary Amines

    Definition:

    Amines with three alkyl or aryl groups attached to the nitrogen.

  • Term: Diazonium Salts

    Definition:

    Salts containing the diazo group, which are important intermediates in organic synthesis.

  • Term: Gabriel Synthesis

    Definition:

    A method for synthesizing primary amines from phthalimide.