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Purpose: To carry out a two-step synthesis of bromophenacetin, exemplifying SN2 Williamson ether synthesis and electrophilic aromatic substitution; solve the puzzle with NMR and melting point to determine the substitution pattern of the brominated product
Assignment Checklist
Assignment Checklist
Exp 3 Pre-Lab quizzes
Exp 3 Notebook Pages
Exp 3 lab report: abstract, in-lab questions, & experimental methods
Phenacetin Synthesis
Phenacetin Synthesis
Part A - Reflux acetaminophen with ethyl iodide and potassium carbonate in acetonitrile. Basic extraction removes unreacted acetaminophen, phenacetin isolated.
Phenacetin Analysis
Phenacetin Analysis
Part B - All the analyses! TLC, Ferric chloride test for phenols, IR, NMR
Phenacetin Bromination
Phenacetin Bromination
Part C - Phenacetin treated with KBrO3, HAc, and HBr to form molecular bromine in situ and brominate phenacetin. Reaction quenched with Na2S2O3 then recrystallized from water. Product analyzed by melting point and 1H NMR to determine the substitution pattern of the product.
<-- Full lab video, Spring '20
Be prepared to make a solid argument to explain which product was formed.
Be prepared to make a solid argument to explain which product was formed.
Done with analysis? Check the in-lab questions to make sure you have everything you need.
Done with analysis? Check the in-lab questions to make sure you have everything you need.
Continue working on the abstract and experimental methods. The questions come once you're writing. Start early so we can help!!
Continue working on the abstract and experimental methods. The questions come once you're writing. Start early so we can help!!
Stand up and celebrate checking this report off your to-do list!
Stand up and celebrate checking this report off your to-do list!
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