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7.4.2.2 - From benzenesulphonic acid

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Introduction to Phenols

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Teacher
Teacher

Today, we're going to discuss phenols, which are important organic compounds characterized by a hydroxyl group bonded directly to an aromatic hydrocarbon. Can anyone tell me the significance of phenols in everyday life?

Student 1
Student 1

They are used in disinfectants and medicines, right?

Teacher
Teacher

Exactly! They have various applications ranging from antiseptics to fragrances. Now, let's move on to how we prepare these phenols.

Preparation from Benzenesulphonic Acid

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Teacher
Teacher

Phenols can be synthesized from benzenesulphonic acid. This process starts with sulphonating benzene using oleum. Who can explain what sulphonation entails?

Student 2
Student 2

It’s when a sulfonyl group is added to benzene, right?

Teacher
Teacher

Correct! After we create benzenesulphonic acid, it reacts with molten sodium hydroxide to form sodium phenoxide. What happens next?

Student 3
Student 3

We acidify it to obtain phenol!

Teacher
Teacher

Exactly! Acidification is crucial as it converts sodium phenoxide back into phenol.

Industrial Importance of Phenols

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Teacher
Teacher

Now that we understand how to prepare phenols, let’s talk about their significance. Why are phenols valuable in industrial contexts?

Student 4
Student 4

They're used in making plastics and as disinfectants.

Teacher
Teacher

Absolutely! They play a role in creating detergents and pharmaceuticals, making them essential in various sectors.

Introduction & Overview

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Quick Overview

This section discusses the preparation of phenols from benzenesulphonic acid and other methods, highlighting the significance of such compounds in various industrial applications.

Standard

In this section, the preparation methods for phenols are detailed, particularly from benzenesulphonic acid. It explains how benzene is sulphonated to form benzenesulphonic acid, which is then converted to phenols. The section also touches on the importance of phenols in industry and their various applications.

Detailed

Detailed Summary

This section provides an overview of how phenols can be synthesized from benzenesulphonic acid and other relevant methods. The process begins with the sulphonation of benzene using oleum, resulting in the formation of benzenesulphonic acid. This acid is then treated with molten sodium hydroxide to produce sodium phenoxide, which upon acidification yields phenol. The relevance of phenols in industrial applications, including their distinct properties and chemical reactivity, is underscored, emphasizing their significance in detergent, antiseptic, and fragrance production. The section sets the foundation for understanding various methods of phenol preparation, important in both academic and practical applications in organic chemistry.

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Audio Book

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Sulphonation of Benzene

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Benzene is sulphonated with oleum.

Detailed Explanation

Sulphonation is a chemical process where a sulfonyl group is introduced into a molecule. In this case, benzene, which is a simple aromatic hydrocarbon, reacts with oleum, a solution of sulfur trioxide in sulfuric acid. This reaction replaces one hydrogen atom of the benzene ring with a sulfonic acid group (-SO3H), resulting in benzenesulphonic acid.

Examples & Analogies

Think of benzene as a single-storey house. When we sulphonate it with oleum, it's like adding a second storey (the sulfonic acid group) to our house. This modification can change how the house (or molecule) behaves and interacts with other chemical substances.

Formation of Sodium Phenoxide

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The benzene sulphonic acid so formed is converted to sodium phenoxide on heating with molten sodium hydroxide.

Detailed Explanation

Once we have benzenesulphonic acid, the next step involves transforming it into sodium phenoxide. This is done by heating the acid with molten sodium hydroxide (NaOH). When they react, the sulfonic acid group is replaced with a sodium ion (Na+), leading to the formation of sodium phenoxide, which is a key intermediate in various organic reactions.

Examples & Analogies

Imagine you have a cake (benzenesulphonic acid) and you'd like to change its topping to something else. Heating it with molten sodium hydroxide acts like a hot oven that allows you to seamlessly change the topping to a frosting made of sodium (sodium phenoxide) without altering the structure of the cake itself.

Acidification to Phenol

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Acidification of the sodium salt gives phenol.

Detailed Explanation

The final step involves acidifying the sodium phenoxide to yield phenol. This is typically done by adding an acid, such as hydrochloric acid (HCl), to the sodium phenoxide solution. The sodium ion is replaced by a hydrogen ion (H+), regenerating phenol, which is an important organic compound used in many chemical processes, including pharmaceuticals, plastics, and antiseptics.

Examples & Analogies

Imagine the sodium phenoxide as a bread dough that has been shaped into a loaf. When you add acid (a warm environment), such as a sourdough starter, it helps to make the bread (phenol) rise and take its final delicious shape, making it ready for baking (used in various applications).

Definitions & Key Concepts

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Key Concepts

  • Benzenesulphonic Acid: A key precursor in the synthesis of phenols.

  • Sodium Phenoxide: Product formed from the reaction of benzenesulphonic acid with sodium hydroxide.

  • Sulphonation: The process of adding a sulfonyl group to an aromatic compound.

Examples & Real-Life Applications

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

Examples

  • The conversion of chlorobenzene to phenol via sodium hydroxide illustrates the preparative pathway for phenols.

  • Benzenesulphonic acid can be converted into phenol using the two-step process of sodium hydroxide treatment followed by acidification.

Memory Aids

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

🎵 Rhymes Time

  • From benzene to acid, we start the chain, / Add NaOH, phenol we'll gain.

📖 Fascinating Stories

  • Imagine benzene entering a lab and meeting oleum; it transforms into benzenesulphonic acid. Then, it meets sodium hydroxide, turning into sodium phenoxide, and finally gets acidified to become phenol, a useful compound in so many things!

🧠 Other Memory Gems

  • S for Sulphonation, P for Phenol — follow the steps, and you'll reach your goal!

🎯 Super Acronyms

B.S.P. - Benzene, Sulphonation, Phenol.

Flash Cards

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Glossary of Terms

Review the Definitions for terms.

  • Term: Benzenesulphonic Acid

    Definition:

    An aromatic sulfonic acid derived from benzene by the addition of a sulfonyl group.

  • Term: Sodium Phenoxide

    Definition:

    A sodium salt of phenol formed during the reaction of benzenesulphonic acid with sodium hydroxide.

  • Term: Sulphonation

    Definition:

    A process of introducing a sulfonyl group (–SO3H) into an organic compound.

  • Term: Phenol

    Definition:

    An aromatic compound consisting of a hydroxyl group (-OH) bonded to a benzene ring.