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Friedel-Crafts Reaction

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The purpose of this experiment is to perform a Friedel-Crafts reaction of ferrocene. Friedel-Crafts reactions are examples of electrophilic aromatic substitution reactions in which the electrophile is a carbocation or an acylium ion. These reactions form a carbon-carbon bond and allows for either an alkyl or acyl group to be substituted onto an aromatic ring. Figure 1 shows the general mechanism for the Friedel-Crafts acylation of benzene. First, the alkyl halide reacts with a strong Lewis Acid catalyst, usually aluminum chloride, to form a complex, which will then lose the halide to the Lewis acid to give the electrophilic acylium ion. The ion, stabilized by resonance, will react with the p-electrons from a double bond in benzene (acting as a nucleophile) and form the cyclohexadienyl cation intermediate and the tetrachloroaluminate anion. The anion then acts as a base to remove a proton from the ring and reform the initial Lewis acid. The ring regains its aromaticity and the product, an aromatic ring with an acyl substituent is fully synthesized. …show more content…

Instead of using a simple benzene derivative as a reactant, the substrate being used is ferrocene, which consists of a central iron atom bounded or sandwiched between two cyclopentadienyl rings. This synthesis also involves greener reagents. As stated above, aluminum chloride is often used as a strong Lewis acid catalyst to start the reaction. However, it is corrosive and can give off considerable quantities of acidic and toxic wastes. Since ferrocene is highly reactive (due to its two cyclopentadienyl rings), AlCl3 can be replaced with a more benign catalyst, phosphoric acid. This reaction will also use acetic anhydride in place of an alkyl halide. Figure 2 shows the mechanism for this

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Experiment 2 Report Scaffold (Substitution Reactions, Purification, and Identification) Purpose/Introduction 1. A Sn2 reaction was conducted; this involved benzyl bromide, sodium hydroxide, an unknown compound and ethanol through reflux technique, mel-temp recordings, recrystallization, and analysis of TLC plates. 2. There was one unknown compound in the reaction that was later discovered after a series of techniques described above.

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Therefore, any reaction with a Grignard cannot be used because of this case that the strong nucleophilic carbon of the Grignard causes. Instead, aprotic solvents like THF and diethyl ether are used. Ethers are mostly used because of the oxygen that makes a complex with the Grignard reagent. Water and acid are highly avoided since they are a proton source. Making sure all glassware and tubes are well dried and that water cannot enter the reaction is a very important step.

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Grignard is a reaction that is crucial to forming the new carbon-carbon bond. This is a two-part lab that teaches new techniques; the purpose of this lab is to introduce realistic organic synthesis and apply acid workup to produce triphenylmethanol. A Grignard reaction is characterized by the addition of a magnesium halide (an organomagnesium halide) to an aldehyde or a ketone in order to form a secondary or tertiary alcohol. These reactions are helpful because they serve as a crucial tool in performing important carbon-carbon bond-forming reactions (Arizona State University, 2018). This experiment aimed to observe the mechanisms of a Grignard reply to synthesize triphenylmethanol from benzophenone using phenylmagnesium bromide as the Grignard reagent.

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It is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve

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Regarding the reaction, Scheme 2-3, one of the free electron pairs of the Oxygen is the HOMO and the empty sp3 orbital of the Carbon is the LUMO. In Scheme 3-4 the oxygen of the water (or perhaps some of the remaining methanol) is the HOMO and the antibinding sp3O-H is the LUMO. 1 During the heating of the solution in which the reaction, Scheme 1-4 takes place, thin-layer chromatography is used to see whether the reaction has been fully, or near fully completed or not. Using a reference of triphenylmethanol to compare. The triphenylmethanol should move slower along the plate of silicon as it has a higher chance of binding to the plate compared to the methyl trityl ether (as alcohols bind stronger to silicon plates than ethers).

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It forms a complex with HBr and extracts it from the aqueous phase into the organic phase where the alkene is. This dehydrates the acid, making it more reactive so that the addition reaction is possible. Rapid stirring is required in order to maximize the surface area

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Step one involves two-carbon acetyl group CoA is added to the four-carbon oxaloacetate to create six-carbon citrate. Step two the citrate loses a particle of water and gains another one. The citric acid is converted to the enzyme aconitase. Step three the isocitrate loses another molecule of carbon dioxide and can be oxidized by forming the five-carbon alpha ketoglutarate. Step four the alpha ketoglutarate is changed to the four-carbon succinyl CoA. A particle of carbon dioxide is deleted and NAD+ is changed to NADH + H+ during the process.

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Introduction:- In organic chemistry the substitution reactions is the most important reactions, especially Nucleophilic aromatic substitution reactions where nucleophile attacks positive charge or partially positive charge As it does so, it replaces a weaker nucleophile which then becomes a leaving group. The remaining positive or partially positive atom becomes an electrophile. The general form of the reaction is: Nuc: + R-LG → R-Nuc + LG: The electron pair (:) from the nucleophile (Nuc :) attacks the substrate (R-LG) forming a new covalent bond Nuc-R-LG.

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