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Organic Chemistry

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Example Data

Sample chromatogram of BTEX mixture

Recording the melting point of salicylic acid, a precursor to the synthesis of aspirin, with Go Direct Melt Station and Vernier Graphical Analysis™

This is only the beginning of what’s possible. See the recommendations below to get started with organic chemistry.

Featured Organic Chemistry Experiments

Using a Gas Chromatograph: Identifying an Unknown Compound

There are many different types of chromatography: paper, thin layer (TLC), liquid (LC), high-pressure liquid (HPLC), and gas (GC). Chromatography is applied in many fields. Biochemists use liquid chromatography to separate proteins; chemists use GC, TLC, and HPLC to identify organic compounds. Forensic scientists and other specialties use gas chromatography for drug tests, toxin screens, and environmental analysis.

All types of chromatography use the same principles that include a stationary phase and a mobile phase. The stationary phase is immobile on the column or the plate and the mobile phase travels from a start point to an end point. Compounds travel from the start to the end at a specific rate depending on their competing affinity for the mobile gas/liquid phase versus the stationary solid phase. Compounds adhere to the stationary phase through dipole interactions, dispersion forces, or ionic interactions.

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The Diels-Alder Reaction of Anthracene with Maleic Anhydride

The Diels-Alder reaction is a member of a class of reactions called cycloadditions. The reaction involves three π bonds, two from the diene and one from the dienophile in a concerted reaction to form a six-membered ring. Since the reaction involves four π electrons in the diene and two π electrons from the dienophile, it is sometimes referred to as a 4 + 2 cycloaddition.

Normal Diels-Alder reactions are favored by electron donating groups on the diene and electron withdrawing groups on the dienophile. The diene must be capable of achieving an s-cis conformation to generate the cis double bond in the cyclohexene product. Acyclic dienes may rotate around a single bond, but dienes locked in the s-trans conformation do not react.

The purpose of this experiment is to form 9,10-dihydroanthracene-9,10-α,β-succinic anhydride by way of a Diels Alder reaction between anthracene and maleic anhydride, as shown in the reaction below. Anthracene acts as the diene and maleic anhydride functions as the dienophile. Xylene (dimethylbenzene) is used as a high boiling temperature solvent so that the reaction will proceed quickly. Melting temperature analysis will be used to characterize the product.

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Friedel-Crafts Acylation of Ferrocene

Friedel-Crafts reactions are examples of electrophilic aromatic substitution reactions. The reaction involves the substitution of hydrogen on the aromatic ring system by an electrophilic carbon species forming a new carbon-carbon bond. Friedel-Crafts reactions may be used to introduce either an alkyl or acyl group.

Ferrocene does not undergo addition reactions typical of cyclopentadiene, but undergoes electrophilic aromatic substitution. The Friedel-Crafts acylation reaction of ferrocene involves the addition of the acylium cation to one of the carbon atoms on the ring, followed by loss of a proton (to solvent). The acylium cation is produced from acetic anhydride, which also serves as a solvent for this reaction. If only one ring reacts, then the product is the orange acetylferrocene. If both rings react, then the product is the red 1,1-diacetylferrocene. The reaction time of this experiment is reduced to limit the formation of 1,1-diacetylferrocene.

Your objectives in this experiment will be to synthesize, isolate, and characterize acetylferrocene. In this experiment you will also become familiar with a technique called column chromatography, which can be used to separate the desired product from unreacted starting material and side products. The compounds are colored which will make it easy to see the separation. Melting temperature analysis will be used to characterize the synthesized product.

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Grignard Formation of Crystal Violet

An organometallic compound is one that contains a carbon-metal bond. The key feature of many of these compounds is that the carbon on the carbon-metal bond carries a partial negative charge. The partial negative charge on carbon makes it basic and nucleophilic; this latter property can be exploited in organic synthesis to help construct carbon-carbon bonds. Organomagnesium compounds are referred to as Grignard reagents.

Crystal violet is a triarylmethane dye which is commonly used in general chemistry classrooms to study spectrophotometry and basic chemical kinetics. Here, you will synthesize crystal violet by preparing a Grignard reagent from the bromine-containing compound 4-bromo-N,N-dimethylaniline. Addition of this Grignard to diethyl carbonate followed by acid hydrolysis ultimately leads to the triarylmethane dye.

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