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Tetraphenylcyclopentadienone Lab Report

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Anthranilic acid, isoamyl nitrite, 1, 2-dimethoxyethane and 2, 3, 4, 5-tetraphenylcyclopentadienone were reacted to yield 1, 2, 3, 4-tetraphenylnaphthalene as an off-white solid in 68%. The low percent yield of 68% could be due to the lack of catalyst to speed up the reaction. Thus, the reactivity decreases and the yield of the 1, 2, 3, 4-tetraphenylnaphthalene also decreases. Furthermore, the reaction time is slow and the simultaneous addition step was done at a faster time of 25 minutes instead of the suggested time of 45-60 minutes. This could have caused the formation of benzyne to stop before it has completely formed. This leads to fewer benzyne undergoing Diels-Alder reaction with tetraphenylcyclopentadienone, resulting in lesser yield of tetraphenylnaphthalene. …show more content…

In the article, Rhodacarboranes as catalysts for oxidative coupling of benzoic acid with diphenylacetylene, it has proven that the reactions catalyzed by [CpRhI2]2 afford the product in 90% yields.2 Furthermore, in the book, Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 1, 2, 3, 4-tetraphenylnaphthalene yield 80% when synthesized by a palladium-catalyzed reaction.3 In both cases, it has proven that the use of catalyst is common to give higher yield of 1, 2, 3, 4-tetraphenylnaphthalene. Catalyst does not increase the yield, but it helps lower the activation energy of the reaction, allowing the reaction to proceed

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Experiment 3 comprised three reactions: formation of dimethyl tetraphenylphthalate, hexaphenylbenzene, and tetraphenylnaphthalene. All 3 reactions used tetraphenylcyclopentadienone as the diene to generate products with high aromatic stabilization. The first reaction was the formation of dimethyl tetraphenylphthalate. A cloudy white solid was formed with 31.1% yield.

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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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