CHEM 2550 Study Guide - Naphthalene, Nitrosonium, Chief Operating Officer
Document Summary
Review of diels-alder reactions, review of diazonium ions. Wednesday, april 15 synthesis of tetraphenylnaphthalene (ch15) Friday, april 17 synthesis of tetraphenylnaphthalene (continued) Goal to generate benzyne from anthranilic acid in the presence of tetracyclopentadienone to produce 1,2,3,4-tetraphenylnaphthalene. Purification - the product is purified by recrystallization, check the purity by melting point. Add the tetraphenylcyclopentadienone you made to a round bottom flask and dissolve it in dimethoxyethane (dme). Fit a claisen adapter, reflux condenser, and addition funnel to the flask. Add the anthranilic acid in dme to the addition funnel. Heat the reaction mixture to reflux using a. Add the anthranilic acid solution and a solution of isoamyl nitrite in dme to the reaction mixture in portions. The isoamyl nitrite solution should be added through the top of the condenser. After the addition is complete, reflux the mixture for an additional 15 minutes. The color can be used to judge the completeness of the reaction.
