9 10 dihydroanthracene 9 10 succinic acid anhydride
Diels alder mechanism pre-lab presentation video
In 1950, Otto Diels and his student Kurt Alder were awarded the Nobel Prize for their work on the reaction that bears their names. Its high yield and sterospecificity make it extremely useful. Since it is possible to exploit the formation of up to four asymmetric carbons in one reaction while also controlling the regioselectivity of the reaction, the Diels-Alder reaction has been widely used in the synthesis of complex natural products.
Reflux is used in a lot of chemical reactions. The reaction is maintained at a constant temperature and in a constant state of mixing by refluxing it in a specific solvent. The temperature of the reaction is determined by the solvent’s boiling point. The solvent is boiled out of the reaction solution, but once it enters the reflux condenser, it easily condenses and returns to the flask.
We’ll be conducting the Diels Alder reaction with maleic anhydride, a widely used dieneophile. Anthracene, a polycylic aromatic hydrocarbon (PAH) used in sulfur, petroleum, and charcoal grilled hamburgers, is the diene we’ll be using. Anthracene is unique in that it provides a variety of diene sites for the Diels Alder addition of maleic anhydride.
Synthesis of copper phthalocyanine dye
The Diels-Alder reaction is described as the reaction of conjugated dienes with an ethylenic or acetylenic compound to produce a six-member cyclic product known as a “adduct.” It’s a [4+2] cycloaddition in which a diene (4 electrons) reacts with a dienophile (2 electrons) to produce a cyclic product. This is a pericyclic or concerted reaction, in which both bond forming and bond breaking take place at the same time. Anthracene (diene) reacts with maleic anhydride (dienophile) to produce 9, 10-dihydroanthracene – 9, 10-endo –, – succinic anhydride. 1
In a 250 mL round bottom flask with a reflux condenser, combine 4 g anthracene, 2.2 g maleic anhydride, and 50 mL dry xylene. Enable the reaction mixture to cool to room temperature after boiling for 30-35 minutes under reflux. If the reaction mixture is colored, add 1 g finely powdered activated charcoal and continue to reflux for another 10-15 minutes. Filter the hot solution through a Buchner funnel with suction, and after cooling, receive colorless product crystals (also known as adduct) in the filtrate. The crude product yields 4.3 g and has a melting point of 256-258 C. Recrystallize the crude product from around 50 mL xylene, filter the hot solution through a small preheated funnel, and allow the filtrate to cool so that the solute crystallizes quickly. The recrystallized product is colorless crystals with a melting point of 260-263 C and a yield of 4.1 g.
Preparation of anthracene b.sc 1st year and 10+2
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362l both diels-alder reactions (#5)
N-(4-pyridinyl)-9,10-dihydroethanoanthracene-11,12-dicarboximide is formed by a condensation reaction between the Diels–Alder adduct of anthracene and maleic anhydride and 4-aminopyridine (L). The formation of a dimeric complex, [Cu2I2L2(MeCN)2], is aided by the reaction of L and CuI in acetonitrile in the presence of saturated NaI. (1). A tetrameric structure, [Cu4I4L3(MeCN)] (2), was obtained by immersing 1 in dichloromethane (DCM), indicating solvent-mediated single-crystal-to-single-crystal (SCSC) transformation. In the development of a cubane style structure from a dinuclear cluster complex, the observed SCSC transformation promoted higher nuclearity. The DCM solution aided the removal of MeCN and L from the crystal of 1 in this study, resulting in an unusual and intriguing SCSC transformation. The SCSC transformation was verified by the different emissions of both complexes under a hand-held UV light, despite the physical appearances of both crystals being identical. At room temperature, Compound 1 exhibited a curious photoluminescence property and was a vividly emissive complex with an intense blue color.