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9.6.6 - Reaction with arylsulphonyl chloride

Interactive Audio Lesson

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Introduction to Aryl Sulphonyl Chlorides

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Teacher
Teacher

Today, we're exploring how aryl sulphonyl chlorides, like benzenesulphonyl chloride, react with amines. Can anyone tell me what a sulphonyl group is?

Student 1
Student 1

Is it a functional group containing sulfur and oxygen?

Teacher
Teacher

Exactly! The sulphonyl group consists of a sulfur atom bonded to two oxygen atoms. When we expose amines to aryl sulphonyl chlorides, they undergo a specific reaction. Let's dive into how primary and secondary amines respond differently to this reagent.

Primary Amines Reaction

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Teacher
Teacher

When a primary amine, say RNH2, reacts with benzenesulphonyl chloride, it forms N-alkylbenzenesulphonamide. What happens to the hydrogen on the nitrogen during this reaction?

Student 2
Student 2

It gets replaced, right? The amine forms a new bond with the sulphonyl chloride.

Teacher
Teacher

Correct! This new sulphonamide has an acidic hydrogen, which is important for its solubility in alkaline conditions. Can you briefly explain how that differs from a secondary amine reaction?

Student 3
Student 3

I think secondary amines form N,N-alkylbenzenesulphonamides, which don\u2019t have that acidic hydrogen!

Teacher
Teacher

That's spot on! Let\u2019s visualize this with a reaction equation to better understand.

Secondary Amines Reaction

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Teacher
Teacher

Now, when we react a secondary amine with benzenesulphonyl chloride, the resulting compound is N,N-alkylbenzenesulphonamide. What can you tell me about its properties compared to the primary sulphonamide?

Student 4
Student 4

It shouldn't have that acidic hydrogen, so it won't be soluble in alkali, right?

Teacher
Teacher

Precisely! This lack of acidity impacts their interaction with alkaline solutions. So how could we potentially use these properties practically?

Student 1
Student 1

We could use these reactions to distinguish between primary and secondary amines!

Tertiary Amines

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Teacher
Teacher

Lastly, let's discuss tertiary amines. Why don't they react with benzenesulphonyl chloride?

Student 2
Student 2

Because they don't have a hydrogen on nitrogen to replace, right?

Teacher
Teacher

Exactly! Their structure doesn't allow for the same reactions. This characteristic helps in differentiating amines in a mixture. What are some other properties we can deduce from these reactions?

Introduction & Overview

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

Quick Overview

The section discusses the reactions of amines, particularly primary and secondary amines, with aryl sulphonyl chlorides to form sulphonamides, highlighting their distinct properties.

Standard

This section examines how aryl sulphonyl chlorides, like benzenesulphonyl chloride, react with primary and secondary amines to create sulphonamides. The differences in solubility and acidity due to the presence of sulphonyl groups in these compounds are also analyzed, including their applications in distinguishing between primary, secondary, and tertiary amines.

Detailed

Detailed Summary\n\nThe reaction of amines with aryl sulphonyl chlorides, particularly benzenesulphonyl chloride (Hinsberg\u2019s reagent), forms sulphonamides, which are crucial for differentiating between types of amines. \n\n### Key Reaction Points\n1. Primary Amines: \n - Reaction with benzenesulphonyl chloride produces primary sulphonamides. \n - The product is N-alkylbenzenesulphonamide, characterized by an acidic hydrogen observable in alkaline solutions.\n - Example Reaction: \n C6H5SO2Cl + RNH2 \u2192 RNH(SO2C6H5) + HCl \n\n2. Secondary Amines: \n - Form N,N-alkylbenzenesulphonamides upon reaction. \n - Lack an acidic hydrogen, making these compounds less soluble in alkaline solutions.\n - Example Reaction: \n C6H5SO2Cl + R2NH \u2192 R2N(SO2C6H5) + HCl\n \n3. Tertiary Amines: \n - Do not react with benzenesulphonyl chloride and therefore do not form sulphonamides.\n\n### Importance of the Reactions\nThis distinction among amines is used for separation and identification, with primary and secondary amines exhibiting different solubility characteristics in alkaline solutions. The analysis of these reactions is vital in organic synthesis and chemical identification processes.

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Audio Book

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Introduction to Aryl Sulphonyl Chloride and Its Reactions

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Benzenesulphonyl chloride (C6H5SO2Cl), which is also known as Hinsberg’s reagent, reacts with primary and secondary amines to form sulphonamides.

Detailed Explanation

Benzenesulphonyl chloride, commonly called Hinsberg's reagent, is a chemical compound that plays a vital role in identifying and differentiating between primary and secondary amines. When this reagent reacts with amines, it produces sulphonamides, which are formed from this chemical interaction. Understanding the nature of this reaction is crucial for distinguishing between types of amines.

Examples & Analogies

Think of Hinsberg's reagent like a specific test for understanding different types of amines. Just as a teacher grades students based on their assignments to see who has done well, this reagent helps chemists identify whether an amine is primary or secondary based on how they react.

Reaction with Primary Amines

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(a) The reaction of benzenesulphonyl chloride with primary amine yields N-ethylbenzenesulphonyl amide.

Detailed Explanation

When benzenesulphonyl chloride reacts with primary amines, the result is the formation of a sulphonamide. In this case, for a primary amine like ethylamine, the product is N-ethylbenzenesulphonyl amide. This means that the nitrogen atom from the amine gets bonded to the sulphonyl group (–SO2), resulting in a new compound that has distinct properties.

Examples & Analogies

Imagine a puzzle where one piece (the primary amine) fits perfectly with another piece (benzenesulphonyl chloride) to create a new picture (the sulphonamide). This new picture represents a unique compound made from the initial pieces.

The Acidity of Sulphonamides

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The hydrogen attached to nitrogen in sulphonamide is strongly acidic due to the presence of strong electron withdrawing sulphonyl group. Hence, it is soluble in alkali.

Detailed Explanation

Sulphonamides, resulting from the reaction between primary amines and benzenesulphonyl chloride, contain a hydrogen atom attached to the nitrogen. This hydrogen bond becomes quite acidic due to the influence of the sulphonyl group that withdraws electron density from the nitrogen. As a consequence, sulphonamides can dissolve in alkaline solutions, which is a useful property in various chemical processes.

Examples & Analogies

Picture pouring sugar into a cup of coffee. When you add sugar (the sulphonyl group) to the coffee (the nitrogen), the coffee becomes sweet (the acidity of the hydrogen) because of the interaction, making it more enjoyable and easier to drink (the solubility in alkali).

Reaction with Secondary Amines

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(b) In the reaction with secondary amine, N,N-diethylbenzenesulphonamide is formed.

Detailed Explanation

When benzenesulphonyl chloride reacts with secondary amines, it leads to the formation of N,N-diethylbenzenesulphonamide. Here, both ethyl groups attached to the nitrogen come from the secondary amine, resulting in a compound that does not contain any hydrogen atoms attached to nitrogen, which influences its chemical behavior.

Examples & Analogies

Think of secondary amines as a special dining table that can only accommodate a certain number of guests (the two ethyl groups). When you invite the benzenesulphonyl chloride to the table (the reaction), you end up with a unique and complete dining experience (the sulphonamide), which is different from when you invite a primary amine.

Tertiary Amines and Their Non-Reactivity

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(c) Tertiary amines do not react with benzenesulphonyl chloride.

Detailed Explanation

Tertiary amines, which have three organic groups attached to the nitrogen atom, do not participate in the reaction with benzenesulphonyl chloride, unlike primary and secondary amines. This lack of reactivity is because there is no hydrogen atom on the nitrogen that can participate in forming sulphonamides.

Examples & Analogies

Imagine a three-tiered cake (the tertiary amine). Since all the tiers (the organic groups) are already covered (attached to the nitrogen), there's no room to add frosting (the sulphonamide formation) like you can with a two-tiered or single-tier cake (the primary and secondary amines).

Application of the Reactions

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This property of amines reacting with benzenesulphonyl chloride in a different manner is used for the distinction of primary, secondary and tertiary amines and also for the separation of a mixture of amines.

Detailed Explanation

The unique way in which primary, secondary, and tertiary amines react with benzenesulphonyl chloride provides a crucial method for distinguishing between these types of amines in a mixture. This distinction is important in synthesizing compounds and purifying chemical mixtures.

Examples & Analogies

Consider a chemistry lab where different colored liquids represent the different amines. When you add a reagent (benzenesulphonyl chloride), it acts like a filter that shows you which colors belong to which group, helping you separate and identify each liquid accurately.

Definitions & Key Concepts

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

Key Concepts

  • Reaction Mechanism: Aryl sulphonyl chlorides react with primary and secondary amines to form sulphonamides.

  • Distinction: Primary and secondary sulphonamides have different solubility and acidic properties.

  • Reactivity: Tertiary amines do not react with aryl sulphonyl chlorides, helping distinguish between amine types.

Examples & Real-Life Applications

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

Examples

  • Primary amine + Benzenesulphonyl chloride \u2192 N-alkylbenzenesulphonamide + HCl

  • Secondary amine + Benzenesulphonyl chloride \u2192 N,N-alkylbenzenesulphonamide + HCl

Memory Aids

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

🎵 Rhymes Time

  • To form sulphonamide, you'll see, Primary amines react with glee.

📖 Fascinating Stories

  • Once upon a time, primary amines met aryl sulphonyl chlorides, forming sulphonamides and leaving behind an acidic hydrogen; secondary amines joined in, but tertiary amines watched without a reaction.

🧠 Other Memory Gems

  • PATS - Primary amines form Acids, Tertiary amines Stay silent, where Secondary amines react with a different outcome.

🎯 Super Acronyms

PAS (Primary Amine Sulphonamide) for remembering sulphonamide formation in primary amines.

Flash Cards

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Glossary of Terms

Review the Definitions for terms.

  • Term: Aryl Sulphonyl Chloride

    Definition:

    An organic compound containing a sulphonyl group attached to an aryl group, typically reacts with amines to form sulphonamides.

  • Term: Sulphonamide

    Definition:

    A type of compound formed from the reaction of sulphonyl chlorides with amines, distinguished by their solubility and properties.

  • Term: Nalkylbenzenesulphonamide

    Definition:

    A sulphonamide derived from a primary amine, having an acidic hydrogen.

  • Term: N,Nalkylbenzenesulphonamide

    Definition:

    A sulphonamide derived from a secondary amine, lacking an acidic hydrogen.