Action Center Practice Problem – Chemical Reactivity and Mechanisms 2(Klein: Chapter 6)Sections Covered: 6.1-6.111. When a substance A(4-methyl-4-propen-1-ol) is treated with dilute, aqueous sulfuric acid, the formation of a new substance B(2,2-dimethyltetrahydrofuran) is observed. The reaction is proposed to take place via an electrophilic addition mechanism where the intermediate carbocation combines with the available nucleophilic alcohol group intramolecularly in order to form a ring. A bronsted acid-base reaction completes the sequence to give the observed product (a). Provide the mechanisms and structural intermediates as required, below.A) Provide the mechanism and intermediates (please answer on a separate sheet)OH+H3OA?+ H2O? + H2O+H3OBB) In principle, there is a second possible electrophilic addition product Cthat could form by an analogous pathway. However, it is not observed.
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This note was uploaded on 09/26/2011 for the course CHEM 3053 taught by Professor Any during the Fall '08 term at The University of Oklahoma.