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What is Acetylation? - Mechanism & Definition

What is Acetylation? - Mechanism & Definition
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  • 0:00 Independent Actions
  • 0:46 Defining Acetylation
  • 1:22 Why Acetylation Happens
  • 2:14 Mechanism
  • 3:14 Lesson Summary
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Lesson Transcript
Instructor: David Jones

David has taught General and Organic Chemistry and has a master's degree in Chemistry.

In this lesson, you will learn all about acetylation. You will learn exactly what it is, why it happens, and about the mechanism by which this particular reaction proceeds.

Independent Actions

Imagine you're back in preschool trying to build a tall tower of blocks with your friend LG. The interesting thing about LG is that she's very independent, so much so that she really would not mind building a tower on her own. Now imagine that your other friend NP is very needy and not very independent at all. He wants to build a tower with you and inserts himself into your game. Naturally, LG simply gives him room and starts to build her own tower since she's so independent anyway. This is exactly what happens in acetylation when you have a good leaving group (LG) and a needy nucleophile (NP). We'll come back to this, but first let's define acetylation.

Defining Acetylation

Acetylation simply involves the addition of an acetyl group to a compound. An acetyl group is made up of a carbonyl group, or carbon double bonded to oxygen, with a methyl group (CH3) on the end. The part of the acetyl group that's attached to your compound is often represented with 'R'.

Acetyl group

If we were trying to perform an acetylation of glucose, for example, we see that we can add an acetyl group onto all of the nucleophilic alcohol groups (-OH groups). We also see that the acetyl group can be abbreviated by the 'Ac' symbol.

Acetylation

Why Acetylation Happens

Remember our analogy about the preschoolers building a tower? Our compound that we are trying to add an acetyl group to is the needy nucleophile, NP. In order to make a good nucleophile, or a compound seeking a positively charged nucleus, we need to make sure we are using a compound that has a site with extra electrons. Oxygen, for example, has extra unbonded electron pairs that make it nucleophilic. All these electrons make it very needy in wanting to work with a partner.

Remember also that the acetyl group needs a strong, independent partner that will act as a leaving group, LG. This means that the acetyl group's old partner has to be very stable on its own.

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