Action Center 12 Chemical Reactivity and Mechanisms 2

Action Center 12 Chemical Reactivity and Mechanisms 2 -...

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Action Center Practice Problem – Chemical Reactivity and Mechanisms 2 (Klein: Chapter 6) Sections Covered: 6.1-6.11 1. 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 + H 3 O A ? + H 2 O ? + H 2 O + H 3 O B B) In principle, there is a second possible electrophilic addition product C that 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.

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