Acylation: Mechanism & Reaction

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  • 0:05 The Nuts & Bolts of Acylation
  • 2:04 Friedel-Crafts…
  • 3:12 Friedel-Crafts…
  • 5:12 Lesson Summary
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Lesson Transcript
Instructor: Danielle Reid

Danielle has taught middle school science and has a doctorate degree in Environmental Health

Did you know the acylation reaction plays an important role in how our body functions at the cellular level? In this lesson you'll learn about the step-by-step process needed for an acylation reaction as well as the mechanism used to carry out this reaction.

The Nuts & Bolts of Acylation

The acylation reaction is an important process for biological and chemical applications. Biologically, this reaction is used in a mechanism critical to numerous cellular processes, such as protein assembly and regulation. In chemistry, you may encounter the acylation reaction being used to produce industrial chemicals for specific purposes, such as making plastic products. Additionally, acylation is used during the processing of pharmaceutical products.

Before we dive into the mechanism of acylation, there are a few items we need to address. First, what is acylation? Acylation is an organic chemical reaction used to add an acyl group to a compound. An acyl group is a functional group that has the molecular formula of RCO.

Here are a few examples of acyl groups.

Different Examples of Compounds With Acyl Groups
example

Think of the R group as an alkyl group that attaches to the CO in acyl's structure. Keep in mind that the CO group is classified as a carbonyl. For carbonyl groups, a double bond joins the carbon and oxygen atoms together.

Second, you need to understand the mechanics of the reaction. In order to carry out this reaction, you must have an acylating agent and a catalyst. An acylating agent is your acyl group or acyl halide. This is added to the compound of interest you would like to see an acyl group attached to. The catalyst is a chemical that speeds up the rate at which the reaction occurs. The catalyst is not consumed during the reaction, which means it will be present before and after the reaction proceeds to completion.

Before we proceed with tackling the steps required to run an acylation reaction, we need to clarify the difference between the terms mechanism and reaction. Did you know there's a difference between these terms? Think of the term reaction as a general name for what you're interested in solving or doing. The term mechanism refers to the type of process performed for a given reaction.

What Is the Friedel-Crafts Acylation Reaction?

Friedel-Crafts acylation is a common acylation reaction. This name was derived based on the scientists who discovered the reaction, Charles Friedel and James Crafts.

Remember the difference between the terms mechanism and reaction? Friedel-Crafts acylation would be the reaction. But what would be the mechanism used to perform this reaction? It would be an electrophilic aromatic substitution mechanism. With the Friedel-Crafts acylation reaction, this mechanism is used to add acyl groups to aromatic compounds.

For a Friedel-Crafts acylation, the acylating agent commonly used is ethanol chloride. The catalyst used, most often, is a type of acyl halide like aluminum chloride.

Here's a basic schematic of the Friedel-Crafts acylation for benzene.

General Schematic Design of the Friedel-Crafts Acylation Reaction
general

With benzene as the aromatic compound, the goal of this reaction is to attach an acyl group from ethanoyl chloride to the benzene ring. In doing so, a ketone product, benzoyl chloride, will be produced. Now that we know the basic schematic of this reaction, let's see how this reaction takes place step by step.

Friedel-Crafts Acylation Mechanism

Here's a step-by-step process of the electrophilic aromatic substitution mechanism, using benzene.

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