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Electrophilic Aromatic Substitution: Mechanisms and resonances | Virtual Lab

Higher Education
Health Sciences
Chemistry
Biology
Electrophilic Aromatic Substitution: Mechanisms and resonances
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About This Simulation

Step into the virtual classroom to learn the secrets behind the electrophilic aromatic substitution. Explore the mechanism of this reaction, the effects of activating and deactivating groups, and the stability of the different resonance structures. Can you help create the perfect perfume?

Learning Objectives

  • Understand the mechanism of the EAS
  • Classify substituents of benzene as activating or deactivating and as ortho, meta, and para directing groups
  • Recognize resonance structures to explain the outcome of any EAS

About This Simulation

Level:
Higher Education
Length:
15
Min
Accessibility Mode:
Available
Languages:
English

Lab Techniques

No lab techniques are listed for this simulation.

Related Standards

University:
  • US College Year 2
  • US College Year 3
NGSS:
AP:
LB:
No lab techniques are listed for this simulation.

Learn More About This Simulation

Can you help create a best-selling scent? Perfumes are everywhere — and so are aromatic compounds. In this simulation, you will learn about the electrophilic aromatic substitution, answer a variety of quiz questions, and then plan the synthesis of your favorite aromatic compound!

Understand the mechanism

If you’re making a perfume, electrophilic aromatic substitution is a key reaction when synthesizing an aromatic molecule of interest. You’ll start your experience in a pharmacy to learn about vanillin. Then you’ll be teleported to the virtual classroom to start your experience. Here, you’ll learn in an interactive way about the mechanism of the reaction, choosing the direction of movement of electrons and the key reagents.

Choose activators and deactivators

Once you’re familiar with the reaction on a benzene ring, you’ll move to the effects of directing groups when combining an electrophile with a mono substituted benzene ring. You’ll place the different substituents on a reactivity graph and choose the right product of reaction so that you’ll be able to characterize a substituent as an activator or deactivator and predict the correct products.

The stability of resonance structures

Understanding the mechanism is not enough when planning a synthetic route. In this activity you’ll have to connect the different resonance structures of a mono substituted benzene attacked by an electrophile with the concept of stability, to help predict the dominant structure at the end of the reaction. 

A real perfume-maker

Now that you’ve acquired all this knowledge, you’re ready to go into a real lab and plan the synthesis of your favorite aromatic compound. Will you create the new best-selling perfume?

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