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What are functional groups?

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Recall that in hydrocarbons, carbon atoms are linked only to other carbon atoms or hydrogen atoms. But carbon atoms can also form covalent bonds with other elements such as oxygen.

A hydrocarbon in which one or more hydrogen atoms have been replaced by an atom or group of atoms is called a functional group. A functional group is an atom or group of atoms that always react a certain way in an organic compound.

You have seen that two compounds like hexanoic acid and ethyl butyrate can have identical molecular formulas but have different properties.

Full image description in following section.

A molecule consisting of a chain of carbon atoms. A carbon atom at the end of the chain is double bonded to an oxygen atom and single bonded to a hydroxyl (OH-) group.

Hexanoic acid, C6H12O2 (stinky sock smell)

Full image description in following section.

A molecule consisting of a chain of carbon atoms. A carbon atom in the middle of the carbon chain is double bonded to an oxygen atom. That carbon atom is also single bonded to an oxygen atom, which is single bonded to a carbon atom, and that carbon atom is bonded to another carbon atom.

Ethyl butyrate, C6H12O2 (pineapple smell)

Notice that each of these compounds consists of a hydrocarbon in which carbon atoms are linked to each other and to hydrogen. But they also include oxygen as a part of their structure. Even though these two molecules share the same molecular formula, the specific arrangement of the atoms (also called their structural formulas) places them into different functional groups. Therefore, they will have different properties, such as two very different smells.

You have already learned about three functional groups: alkanes, alkenes, and alkynes. Watch the video to learn about five new and more complex functional groups and how to identify them.

You may want to use the study guide to follow along. If so, click below to download the study guide.

Download PDF Transcript (opens in new window)

When we discuss elements, and how they behave, we often talk about the group they are in on the periodic table. This is because elements from the same group exhibit similar characteristics. In much the same way, when we talk about organic chemistry, rather than talking about specific compounds, we will often discuss functional groups.

Functional groups are groups of molecules that, based on their similar molecular structures, react similarly to one another.

Now, you’ve already encountered a few functional groups. We’ve looked at alkanes, alkenes, and alkynes in previous lessons. In this lesson, we are going to look at more complex functional groups, namely, alcohols, aldehydes, ketones, acids, and esters. We will learn what makes them structurally unique, and how we can identify them.

To begin, let’s look at alcohols. Here, we have a diagram of an alcohol called propanol. As you may have deduced, the name stems from the fact that there are 3 carbons in the central carbon chain, corresponding to the prefix prop-. If we shorten that carbon chain by one, we get an alcohol called ethanol, a common fuel additive, and if we shorten it by one more, we get methanol. These are all alcohols. What makes them an alcohol is not the specific carbon chain, but rather this piece here, called a hydroxyl group. So, when we represent functional groups, we know that there could many different hydrocarbon chains that make this molecule. In the last lesson you saw just how complicated those can get. So, to show the general structure for all alcohols, we replace that hydrocarbon with the letter R, representing the rest of the molecule.

And this here represents the alcohol functional group. It is some hydrocarbon with a hydroxyl group attached to the end. We’re going to use this method of representation going forward.

The next group we want to look at are called aldehydes. Aldehydes look like this. We have our hydrocarbon, represented by the R, but the carbon at the end of the chain is doubled bonded to an oxygen. This carbon-oxygen double bond is called a carbonyl group. We’ll see that in other functional groups as we move forward. Examples of aldehydes include formaldehyde, which you may have used in a biology class to preserve certain tissue samples, and vanillin, which is the chemical that gives vanilla its unique flavor.

Next, let’s look at ketones. Ketones have two different carbon chains, which we mark as R1 and R2. Where they meet, there is a carbonyl group, that carbon oxygen double bond. Examples of ketones include acetone, which is the key ingredient in nail polish remover, and fructose, which is the sugar that makes fruit sweet. Also, you may have heard of the ketogenic, or keto, diet. It gets its name from the fact that when on that diet, the body produces more of these chemicals.

Next, we’ll look at acids. The structure of this functional group looks like this. Now, you may notice that this looks nothing like the Arrhenius acids we’ve seen before in this course, and that’s true. This is a special group of acids called carboxylic acids. That name comes from the fact that connected to the hydrocarbon is a carbonyl group – that carbon oxygen double bond – and a hydroxyl group. Examples of carboxylic acids include amino acids, which are the building blocks of proteins – and by extension life itself, as well as acetic acid, which is the defining component of vinegar.

Alright, the last functional group we are going to look at are esters. Here is the basic structure of an ester. At the center of this molecule we have a carbon that is bonded to two oxygens. One of the bonds is a double bond, signifying a carbonyl group, and the other is a single bond. We have two hydrocarbons: one is bonded to the carbon, and the other is bonded to the single bonded oxygen. It’s like the COO group is in a hydrocarbon sandwich. We see esters all over the place, as they are really important in plastics and oils. Examples include polyester, a common plastic-based fabric, and many essential oils and lipids, which are the fats produced by plants and animals.

And those are the five critical functional groups we need to know: alcohols, aldehydes, ketones, acids, and esters. Each functional group has important structural characteristics that define how they react with other chemicals, and by looking at them in their simplest form, we can better understand why they exhibit their unique set of traits.


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Let's Practice

Organic compounds can be classified into families according to structural features called functional groups. In the video, you learned about the functional groups that are found in alcohols, aldehydes, ketones, carboxylic acids, and esters. Match each functional group with the correct description.

To match items, click or tap an item in the left column and then click or tap its match in the right column. If you change your mind, make a different choice. Once you have matched all items, click "Check Answers" to see how you did. Click "Reset" to try again.
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Question

How is the structure of an ester group related to the structure of a carboxyl group?

An ester group is a carboxyl group in which the hydrogen of the hydroxyl group is replaced by an "R".