With a molecular formula of COOH, structure is of utmost importance when it comes to

carboxyl groups. Discover how to identify the properties of this functional group. Updated:
10/11/2021

What's a Carboxyl Group?

A carboxyl group is a very common functional group seen in chemistry. A carboxyl group is
defined as having a carbonyl and hydroxyl group both linked to a carbon atom. To refresh your
memory, a carbonyl group is a carbon double-bonded to an oxygen, and a hydroxyl group is an
OH group. As a side note, don't be fooled by the term carboxy group. This is just another way
to say carboxyl group.

A great way to make sure you know you are dealing with carboxyl is to be on the lookout for
two things: an OH and a carbon double-bonded to an oxygen. Better yet, if you look at the word
carboxyl we can break it down into two parts: 'carb' and 'oxyl.' When you see 'carb' think carbon
atom. When you see '-oxyl' think hydroxyl group. The molecular formula for a carboxyl group is
COOH.

Carboxyl Group Formula

When you hang out with carboxyl as an organic compound, you receive the benefit of joining
the club of acidity. Carboxyl groups will make organic compounds acidic because of their own
ionizing property. Let's dig a little deeper on this subject of carboxyl's ionizing property.

Carboxyl groups will ionize themselves by letting go of the hydrogen atom on the hydroxyl
group. This process of ionizing themselves occurs often. When the hydrogen atom is free
floating, it is now called a free proton. It is the release of this hydrogen atom that makes a
carboxyl group acidic.

But what does that mean for the oxygen atom? Well, instead of remaining lonely and sad that
hydrogen left, the oxygen atom will become negatively charged. As a comeback to losing his pal
hydrogen, the oxygen atom will go as far as sharing this negative charge with the second
oxygen atom present. By sharing a negative charge between both oxygen atoms, the carboxyl is
able to remain stable while ionized.

Carboxyl remains stable when ionized.

Wait, so why is the carboxyl group so willing to let the hydrogen go? The answer goes back to
stability. When hydrogen is present, carboxyl is linked by a single bond to the hydroxyl group
and a double bond to the oxygen atom. These two different bonds make carboxyl feel uneasy
as more energy is required to maintain its configuration. When hydrogen leaves, the double
bond is broken, and now carboxyl is free to not only lower its energy state but also increase its
stability. Hence, it makes perfect sense why carboxyl is so quick to let hydrogen go and turn
into an acid.

Properties of carboxyl groups

Carboxyl vs. Carbonyl

Now I am sure you probably already thought, 'Hey carboxyl sounds similar to the term
carbonyl.' There is actually some truth to that statement. Think of carbonyl and carboxyl groups
as part of the same functional group family. The carbonyl does not have a hydroxyl group, like
carboxyl does. So, although they may sound very similar, they are quite different. Here's a
reference to make sure you can see the difference between carbonyl and carboxyl groups.

Carbonyl and carboxyl groups

There is a good reason why carboxyl and carboxylic acid are best buddies. When you see an
organic compound with a carboxyl group, guess what it is called? That's right, a carboxylic acid.
If this sounds confusing, here you see the difference between a carboxylic acid and a carboxyl
group. Just remember, you will never a see a carboxylic acid compound without a carboxyl
group present. They are best buds - glued to each other's hips!

Carboxyl and carboxylic acid

Lesson Summary
Let's Review. Carboxyl groups are functional groups with a carbon atom double-bonded to an
oxygen atom and single bonded to a hydroxyl group. The molecular formula is COOH. Carboxyl
groups missing a hydrogen atom are de-protonated and ionized. Ionized carboxyl groups act as
acids, require less energy and are more stable. Electron sharing between oxygen atoms on
ionized carboxyl groups increases stability. Carboxyl groups are different from carboxylic acids
and carbonyl groups because of their side chains.

Learning Outcomes
The process of memorizing this lesson's details about carboxyl groups could prepare you to:

 Recognize the properties of carboxyl groups

 Identify the molecular formula for carboxyl groups
 Distinguish between carboxyl groups, carboxylic acids and carbonyl groups4