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Tetraphene Lab Report

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Results and discussion In this research, a diene (tetraphenylcyclopentadienone) was reacted with three alkyne dienophiles (acetylene dicarboxylate, diphenyl acetylene, and benzyne) to form tetraphenylphtalate, hexaphenylbenzene, and tetraphenylnaphthalene respectively. On the other hand, the diene(anthracene) was reacted with the dienophile(benzyne) to form triptycene. In the first reaction, diene (tetraphenylcyclopentadienone) interacted with the dienophile(acetylene dicarboxylate) to produce tetraphenyl phthalate as shown in the reaction mechanism 1. Reaction mechanism 1 In the second reaction, diene(tetraphenylcyclopentadienone) reacted with the dienophile(diphenylacetylene) to generate hexaphenylbenzene as described in the reaction mechanism 2. …show more content…

Reaction mechanism 3 In the fourth reaction, diene(anthracene) reacted with the dienophile(glyme) to produce triptycene as indicated in the mechanism 4. Reaction mechanism 4 In the first, second and third reactions the dienes(tetraphenylcyclopentadienone) were the same while the fourth reaction had a different diene(anthracene). All the dienophiles were

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Benzyne Formation and the Diels-Alder Reaction Preparation of 1,2,3,4 Tetraphenylnaphthalene Aubree Edwards Purpose: 1,2,3,4-tetraphenylnaphthalene is prepared by first producing benzyne via the unstable diazonium salt. Then tetraphenylcyclopentadienone and benzyne undergo a diels-alder reaction to create 1,2,3,4-tetraphenylnaphthalene. Reactions: Procedure: The reaction mixture was created. Tetraphenylcyclopentadienone (0.1197g, 0.3113 mmol) a black solid powder, anthranilic acid ( 0.0482g, 0.3516 mmol) a yellowish sand, and 1,2-dimethoxyethane (1.2 ml) was added to a 5-ml conical vial.

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Discussion: 1. The Diels alder reaction has to be heated slowly to 60-70 degrees Celsius because if it is heated too quickly and the temperature gets too high the 2,3-dimethyl-1,3-butadiene will boil. A round bottom flask was attached to a water condenser to prevent any product from boiling and evaporating out during the heating process. For the hydrolysis part of the experiment the temperature needed to be 60-80 degrees Celsius to melt the cyclic anhydride but also prevent the reaction from boiling and losing product from evaporation. Lastly the final product crystals were not washed with hot water because it would have melted the crystal thus cold water was used.

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6.7, 6.8 Synthesis, Decomposition, and Displacement Reactions Kelly Mok SNC2DE-A Mr. Cox Partner: Nidhi S. Lab performed: September 18 & 19, 2014 Due: September 26, 2014 Purpose The purpose of this experiment is to observe and compare synthesis, decomposition, single displacement and double displacement reactions and the physical and chemical reactions that occur as a result. Hypothesis

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The objective of this two-part experiment was to in Part I, create 4-tert-butylcyclohexanone via oxidation of 4-tert-butylcyclohexanol to provide a source of ketone for reduction procedures. Part II of the experiment was conducted preforming a series of reduction reactions in effort to asses the diastereoselectivity of aluminum isopropoxide (MPV reduction), sodium borohydride (NaBH4), and L-selectride when reacted with 4-tert-butylcyclohexanone. The methods used for analysis were TLC, IR, and 1HNMR spectroscopy. An oxidation of 4-tert-butylcyclohexanol was conducted to produce the ketone, 4-tert-butylcyclohexanone using oxidizing reagent, sodium hypochlorite in glacial acetic acid solvent.

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Dalia El-Desoky Organic Chemistry II Lab 05 8 February 2017 Dehydration of 2-methylcyclohexanol Introduction: Dehydration is a common reaction in Organic Chemistry used to produce carbon-carbon double bonds. The dehydration mechanism involves the removal of water from an alcohol to form an alkene. In this experiment, 2-methylcyclohexanol will undergo acid catalyzed dehydration in heat to form three products: 1-methylcyclohexene, 3-methylcyclohexene, and methylenecyclohexane [1]. The reaction is carried out in a Hickman still filled with Drierite, a drying agent composed of CaSO4 which absorbs water.

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The possible explanations and changes to make are similar to the previous questions. Conclusion and Future Experiment 18. The identity of the product and unknown were 4-tert-butylbenzyl phenol ether and tert-butyl phenol respectively. The key to making this discovery was the melting point and TLC results!

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Abstract: The main goal in our reaction was to use benzyl alcohol and (carbethoxymethylene)triphenylphosphorane along with a Wittig reagent to create ethyl cinnamate. Throughout the experiment, many observations were recorded that demonstrated the production of our product, including the production of a thick black substance. Synthesis steps were followed involving PCC and other reagents such as DCM to produce a 62.5% yield following the TLC and flash chromatography. IR and NMR were taken on the product to be able to be analyzed and discover what was made throughout the steps of synthesis. After analyzing the IR, NMR, and TLCs, it was determined that the product that was predicted was in fact present in the organic compound.

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In order to achieve the meso product, the double bond in between the carbons attackss molecular bromine which in turn breaks the bromine-bromine bond. The attacked bromine forms a cyclic bridged bromine ion intermediate with a positive formal charge on it. While centered in between phenyl groupscarbons, the bromine that was notn’t attacked gainsned the electrons from the bromine-bromine bond making the molecule negative. The nonattacked bromine then attacks one of the carbons breaking one of the the bridged bromine bonds. The nonattacked bromine ends up on the opposite side of the bromine intermediate.

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There, the dehydration process was successful. Instead, one of the three products, Methylenecyclohexane, 3-Methylcyclohexene, or 1-Methylcyclohexene, was able to form. The E1 mechanism allows for this reaction to for all three products under thermodynamic conditions. The phosphoric acid protonated the OH leaving group, thus turning it into water, a suitable leaving group. After the water molecule departed, the carbocation can form two of the three products, 1-methylcyclohexene and 3-methylcyclohexene, by the elimination of an H on an adjacent carbon.

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The abundant of esters, which serves as the electron withdrawal group, propels the effectiveness of this reaction. In the present case, the central ring of the anthracene possesses the characteristic properties of a diene, electron-rich, system [1]. Thus, this aromatic compound reacts with the 9 and 10 positions of the maleic anhydride dienophile, electron-poor, by 4 +2 cycloaddition [1]. 9 and 10 are the position of preference because it is where new bonds can be made without destroying the aromatic formation of the other two rings. This reaction results in a six-membered ring bridged on the 9 and 10 positions of anthracene.

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After analyzing the IR spectrum and the fingerprint region of the product, my product most closely corresponded to that of 2-heptanone meaning the unknown reactant would be

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As a result, we were able to successfully form the desired product, tetraphenylcopentadienone. We were first able to confirm this through the color of our final product, purple, as this is the expected color of the final product. As part of experiment 20A, we begun with 4.1508 g of the previously created benzoin. Through the oxidation procedure, we obtained 5.9055 g of crystals as our product.

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