Mason Delacroix
Fluorenone is an aromatic organic compound that can be found naturally in wine grapes (Vitis vinifera). It has a five-membered ring with a carbonyl group attached and two benzene rings fused on either side. The carbonyl group is a carbon-oxygen double bond, and when this group is bonded to two other carbon atoms, as in fluorenone, it is known as a ketone. Fluorenone is soluble in organic solvents like chloroform and ethanol but insoluble in water. Interestingly, fluorenone can be converted into an alcohol through a reduction reaction with sodium borohydride. This transformation is evident in experiments where fluorenone, a ketone, is reacted with sodium borohydride to yield fluorenol, an alcohol.
| Characteristics | Values |
|---|---|
| Chemical Class | Ketone |
| Aromatic Compound | Yes |
| Carbonyl Group | Carbon-Oxygen Double Bond |
| Solubility | Soluble in organic solvents like chloroform, methanol, ethanol, dichloromethane, and acetonitrile but insoluble in water |
| Density | 0.9 mL |
| Molecular Weight | 180 g/mol |
| Conversion to Alcohol | Can be reduced to fluorenol, an alcohol, by reacting with sodium borohydride |
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What You'll Learn
9-Fluorenone is a ketone
The compound can be found naturally in Vitis vinifera, or wine grapes, and can also be synthesized in a few ways. One method is through an oxidation reaction of fluorene with glacial acetic acid and sodium hypochlorite solution. Another is by subjecting a suitable aromatic compound to catalytic oxidative cracking.
In terms of its solubility, 9-fluorenone is soluble in various organic solvents, including chloroform, methanol, ethanol, dichloromethane, and acetonitrile. However, it is insoluble in water, which is a common characteristic of many organic compounds.
In a laboratory setting, 9-fluorenone can be used in experiments to reduce a ketone to an alcohol using sodium borohydride. This reaction results in the creation of an alcohol, specifically fluorenol, which has an OH bond. The CO double bond characteristic of a ketone is no longer present in the final product.
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Ketones can be reduced to alcohols
Ketones are organic compounds with the grouping -CHOH. They can be reduced to alcohols through a process called carbonyl reduction. This involves the nucleophilic addition of a hydride ion to the carbonyl carbon, forming a C-H single bond and a tetrahedral alkoxide ion intermediate. The alkoxide ion is then converted to an alcohol through reaction with a proton source.
There are several ways to carry out this reaction. One method involves using sodium tetrahydridoborate (previously known as sodium borohydride) as the reducing agent. The reaction can be carried out in an alkaline water solution or in an alcohol solvent like methanol, ethanol, or propan-2-ol. Another method involves the use of lithium aluminium hydride, a strong reducing agent that is effective for reducing carboxylic acids and esters to alcohols.
The reduction of ketones can also be achieved through catalytic hydrogenation or Birch reduction under mild conditions. In the reduction of cyclohexanones, for example, the hydride source can attack axially or equatorially to produce different types of alcohols.
It is important to note that ketones are less reactive than aldehydes due to greater steric effects and the presence of an extra alkyl group, which contributes electron density to the C=O bond, making it less electrophilic. As a result, aldehydes require milder reagents and conditions for reduction.
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9-Fluorenol is an alcohol
Ketones can be reduced by sodium borohydride to form alcohols. In a lab experiment, fluorenone can be reduced to fluorenol using sodium borohydride, resulting in an alcohol. The procedure involves dissolving sodium borohydride in ethanol, adding the ketone compound, and then adding sulfuric acid. The solution is then separated, heated, cooled, filtered, and washed with ethanol and water. The critical peaks for fluorenone, indicating the presence of a ketone, are no longer detected in the sample product, and a new peak indicates the presence of an OH bond, characteristic of an alcohol.
Fluorenol is the desired product of the reaction of ketone reduction by sodium borohydride. The percent yield of the reaction can be 100%, but further testing is required to prove the identity of the product as fluorenol.
Fluorenol is also involved in oxidation reactions to form fluorenone. In an organic chemistry lab experiment, the oxidation of 9-fluorenol with sodium hypochloride solution and acetic acid results in the synthesis and isolation of 9-fluorenone. This experiment also involves the practice of TLC analysis to determine the completeness of the reaction.
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Ketones can be synthesised from secondary alcohols
Ketones are stable compounds that are important in chemistry as they serve as intermediates. They are used in a wide range of applications, including making polymers, solvents, and medical applications. The synthesis of ketones from secondary alcohols is a well-known process in organic chemistry. This process involves the oxidation of secondary alcohols to form ketones.
The oxidation of secondary alcohols to ketones is a crucial step in the synthesis of various organic compounds, both in the laboratory and in industrial settings. It is important to note that tertiary alcohols, unlike primary and secondary alcohols, are resistant to oxidation due to the absence of hydrogen atoms attached to the carbon with the hydroxyl group. This makes it challenging to form carbonyl groups without disrupting the molecule's carbon framework. Therefore, tertiary alcohols are not typically involved in these oxidation reactions.
Several catalytic methods are available for the synthesis of ketones from secondary alcohols. One method involves the use of a nitroxyl-radical-catalyzed oxidation with diisopropyl azodicarboxylate (DIAD). This process allows for the conversion of various primary and secondary alcohols to their corresponding aldehydes and ketones without overoxidation to carboxylic acids. The amount of DIAD used determines whether 1,2-diols are oxidized to hydroxyl ketones or diketones.
Another catalytic method employs TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) and a quarternary ammonium salt as catalysts, along with Oxone as an oxidant. This system has proven successful for the synthesis of ketones, even with sensitive silyl protective groups. Additionally, the use of o-iodoxybenzoic acid (IBX) or 2-iodosobenzoic acid (IBA) as co-oxidants in the presence of Oxone has been demonstrated as an effective approach.
Furthermore, the combination of FeCl3, L-valine, and TEMPO has been shown to oxidize a wide range of primary and secondary benzyl, allylic, and heterocyclic alcohols into aldehydes and ketones with good to excellent yields. This reaction occurs in the presence of oxygen and results in the formation of the corresponding carbonyl groups.
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9-Fluorenone is an aromatic organic compound
9-Fluorenone is an ortho-fused tricyclic hydrocarbon. Its structure consists of a benzene ring on the left and another on the right, with both fused to a five-membered ring in the middle. This five-membered ring has a carbonyl functional group attached, which is a carbon-oxygen double bond. This carbonyl group is what defines 9-fluorenone as a ketone. Ketones are identified by the presence of a carbonyl group bonded to two other carbon atoms.
9-Fluorenone is naturally found in Vitis vinifera (wine grapes). It can also be synthesised in three ways: through an oxidation reaction of fluorene with glacial acetic acid and sodium hypochlorite solution; by fluorene fractions with a quaternary ammonium salt; or by subjecting a suitable aromatic to catalytic oxidative cracking. The fluorene that 9-fluorenone is synthesised from is also an organic compound, derived from coal tar or the dehydration of diphenylmethane.
Converting fluorene to 9-fluorenone can yield desirable physical and chemical properties that fluorene does not possess. For instance, 9-fluorenone is less dense and has a higher melting point. These characteristics lend themselves to applications that fluorene cannot provide.
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Frequently asked questions
9-Fluorenone is an organic compound.
9-Fluorenone is a ketone. This is because it has a carbonyl group (a carbon-oxygen double bond) that is bonded to two other carbon atoms.
9-Fluorenol is an alcohol.
9-Fluorenone can be used in a lab experiment to make 9-fluorenol by reducing the ketone group with sodium borohydride.
9-Fluorenol can be oxidised to make 9-fluorenone.
