Bromination of Acetanilide: Mechanism & Explanation

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  • 0:04 Bromination of Acetanilide
  • 1:11 Overall Reaction Structure
  • 1:46 Reaction Mechanism
  • 3:47 Lesson Summary
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Lesson Transcript
Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

The primary focus of this lesson is on a specific organic chemistry reaction: namely, the bromination of acetanilide. Our goal is to understand how the reaction happens in terms of its mechanism.

Bromination of Acetanilide

Are you one of those people that likes to know all the details about something, or do you just like to know the bare essentials? For instance, when you're traveling on a road trip, do you need to know where you're stopping, for how long, what you'll do there, etc.? Or do you simply need to know your final destination and leave the details to chance? Perhaps you're not a detail-oriented person, but for some, the beauty is in the details and they must know everything they possibly can about something.

Explanations of organic chemistry reactions can be more basic or more detail-oriented. Some people just want to know that if reactant 'A' is combined with reactant 'B' product 'C' will be formed. Others, though, want to know exactly how 'A' combines with 'B' to form 'C' in terms of the reaction mechanism. A reaction mechanism tells a detailed story of how a reaction happens, and it uses curved arrows to represent electron flow as well as bond-making and bond-breaking events. Today, we will be diving into the reaction mechanism behind the bromination of acetanilide and exploring how the reaction happens in terms of its mechanism. Let's go get those details!

Overall Reaction Structure

Just like when you plan a road trip, you look at where you're starting and where you want to end up. Let's do the same with bromination (which is basically just the addition of a bromine atom) of acetanilide to get a big-picture idea of what's going on. In this specific reaction, we're taking the compound known as acetanilide and adding a bromine atom to the benzene ring. This particular reaction won't happen all on its own, so we employ the use of an iron (III) bromide (FeBr3).


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Notice that we need molecular bromine (Br2) as well for the reaction to happen, which we will discuss in the coming sections.

Reaction Mechanism

Now that we have a big-picture idea of what's going on for this reaction, let's break down the steps of the mechanism to see exactly how we get from the starting point to the end product.

1. Formation of Electrophilic Bromine Species

The first thing we need to generate is a bromine species that is electrophilic. In organic chemistry, an electrophile is anything that has some sort of positive charge character that can react with a nucleophile, while a nucleophile is something that has negative character and donates electrons. Here's where our catalyst comes into play. A molecule of bromine reacts with the FeBr3, and when this happens, notice how one of the bromine atoms now has a positive charge. This is our electrophilic bromine species.


Formation of electrophilic bromine species
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