Fluorenone: Structure, Solubility & Polarity

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

In this lesson we will be taking an in-depth look at an organic compound known as fluorenone. Our primary points of discussion will be on its structure, solubility, and polarity.

Lecture Day in Organic Chemistry

It's the day of Tom's organic chemistry lecture class. Recently, his professor has been going over aromatic compounds, and today they will specifically discussing an aromatic compound called fluorenone, used in making antimalarial drugs.

Aromatic compounds in organic chemistry play a vital role in applications like pharmaceuticals, pesticides, and materials, just to name a few. Let's listen in on the lecture and learn along with the class about the structure, solubility, and polarity of fluorenone.

Structure of Fluorenone

General structure of fluorenone

Tom's professor gets things kicked off by introducing the class to the structure of fluorenone. Fluorenone is an aromatic compound that contains a five-membered ring with a carbonyl group attached and two benzene rings fused on either side. Let's break that down a bit.

'Aromatic' means that the compound contains an alternating network of double and single bonds all the way around each benzene ring. Notice that the five-membered ring that looks like a pentagon is sandwiched right in the middle of each benzene ring. These types of ring systems that are joined together like that are called fused ring systems. We could say that the five-membered ring has a benzene ring 'fused' to each side of it.

A carbonyl group in organic chemistry is always defined as a carbon-oxygen double bond. If the carbonyl group is bonded to two other carbon atoms (as with fluorenone), than that particular functional group is known as a ketone.

Solubility of Fluorenone

The next thing Tom's professor discusses is the solubility of fluorenone. When we talk about the solubility of a compound, we refer to whether or not it will form a solution with a given solvent, in other words, will it dissolve. If it does, we say that the compound is soluble. If it doesn't, it is insoluble.

Fluorenone is soluble in a wide range of organic solvents (solvents that are carbon-hydrogen based) including things like chloroform, methanol, ethanol, dichloromethane, and acetonitrile.

An important thing to realize however, is that fluorenone is NOT soluble in water. This is actually the case for a lot of organic compounds. The reason will become more apparent when we talk about its polarity in the next section.

Polarity of Fluorenone

The last thing Tom's class discusses is the polarity of fluorenone. Compounds are generally either:

  • polar - meaning there is an unequal sharing of electrons due to a difference in electronegativity between two atoms
  • non-polar - meaning basically the opposite; there is no difference in electronegativity between atoms and the sharing of electrons is equal.

Oxygen is more electronegative than carbon, meaning that it has the ability to attract electrons (in the form of bonds) towards itself. Think about two dogs of unequal strength playing tug-of-war. The stronger dog will ultimately be able to pull the rope towards itself due to its greater strength. The same is true for atoms, and oxygen is 'stronger' than carbon and can pull electrons towards itself.

Fluorenone is polar. Oxygen pulls electrons toward itself due to the difference in electronegativity.
polar fluorenone

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