Reduction of Fluorenone to Fluorenol

Instructor: Korry Barnes

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

In this lesson, we are going to be learning about a specific chemical reaction that involves a compound called fluorenone and its reduction to an alcohol called fluorenol.

Reducing Ketones to Alcohols

Maggie loves organic chemistry, mainly because she wants to one day have a career as a pharmaceutical chemist and having a good understanding of organic chemistry is crucial to that field of science. In today's lab experiment, the class is going to be learning how to perform the reduction of a ketone to produce an alcohol. They have already studied about the concept in lecture, but now they are going to see how it works from a practical standpoint.

The specific reaction they will be carrying out is the reduction of a compound called fluorenone to give the alcohol fluorenol. Let's learn about how this reaction works!

What is Fluorenone?

Fluorenone is an aromatic organic compound that is made up of three carbon rings fused together. There are two benzene rings with a five-membered ring sandwiched in between them. At the very top carbon of the five-membered ring, there is a carbon-oxygen double bond, also called a ketone.

Structure of fluorenone

Reduction of Fluorenone

So, how does this transformation work? The fluorenone will have the ketone functional group reduced to an alcohol by reacting fluorenone with sodium borohydride, whose chemical formula is NaBH4. Sodium borohydride is a very mild and common reducing agent and is excellent for converting ketones to alcohols. The overall reaction is as follows:

Reduction of fluorenone to fluorenol by sodium borohydride

Mechanism of the Reduction

Let's take a moment and think about how the reduction reaction happens. Sodium borohydride, although it looks like a complicated compound, is simply a source of hydride ions for the reaction. The hydride ion is a single hydrogen atom with a negative charge. In the first step of the reaction, a hydride ion attacks the carbon-oxygen double bond, breaking it into a carbon-oxygen single bond.

First step in the reduction of fluorenone in which a hydride ion attacks the carbon-oxygen double bond

In the last step of the mechanism, a water molecule provides a hydrogen atom to the negatively charged oxygen in fluorenone, forming our final product, fluorenol. In organic chemistry, an oxygen with a negative charge is called an alkoxide ion.

Last step in the reduction of fluorenone in which a water molecule provides a hydrogen atom to form fluorenol

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