Acetanilide: Formula, Resonance & Derivatives

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  • 0:04 Acetanilide
  • 0:50 Structure & Chemical Formula
  • 1:56 Resonance Structures
  • 3:08 Derivatives
  • 3:57 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 will be on a specific organic compound known as acetanilide. Our points of discussion regarding the molecule will be its chemical formula, resonance structures, and important derivatives.


When you have a headache or muscle soreness what do you typically use to help make you feel better? Do you reach for Aleve, aspirin, or maybe Tylenol? There certainly are a lot of choices out there for over-the-counter pain management and most likely you have a particular option that works best for you and your needs.

Did you know that there's a pain medication that used to be quite common but is no longer in use? As it so happens, it's the main topic of our lesson today.

It's called acetanilide and although it used to be a commonly prescribed medication for light pain management, it quickly lost its allure among medical professionals after some serious toxicity concerns began to arise. Today, we're going to be talking about acetanilide in terms of its chemical formula, resonance structures, and some of its important derivatives. Let's get started!

Structure & Chemical Formula

Acetanilide is an organic chemical compound (meaning it's composed of carbon and hydrogen mostly) that is classified as an amide in terms of its functional group. This means that it has the carbonyl group (carbon-oxygen double bond) bonded directly to a nitrogen atom. It also contains an aromatic ring, which is a ring composed of six carbon atoms and an alternating double-single-double-single bonding pattern all around the ring.

Acetanilide is an organic compound that contains an amide functional group and an aromatic ring

Acetanilide only contains four types of atoms, which include carbon, hydrogen, nitrogen, and oxygen. It's chemical formula tends to be written as C6 H5 NHCOCH3. The reason it's written that way is to help signify the different portions of the molecule. For instance, the C6 H5 portion of the chemical formula represents the aromatic ring, and the NHCOCH3 piece represents the amide functional group.

A lot of times, it's helpful to break molecules up into parts in order to simplify them. It's kind of like taking what looks like a complex math problem. Although you may think it's impossible to solve, once you break it down into simpler portions it begins to make more sense and is not so intimidating.

Resonance Structures

It turns out that acetanilide's structure can be represented by either of two structures, which are related to each other by resonance. Resonance structures are different representations of the same molecule, due to the arrangement of bonds and electrons. The first structure of acetanilide is exactly like the one we saw previously, but notice how the second is different.

Acetanilide can be represented by either of two resonance structures

In the second resonance structure, notice that the lone pair of electrons that was on the nitrogen atom are gone, and there is a negative charge on the oxygen atom. Also, there is now a double bond between nitrogen and the carbon atom of the carbonyl group. This is a very nice example of how resonance works. We haven't changed anything about the molecule's identity, just the way the bonds are distributed between the atoms.

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