CHEM 233 Lecture Notes - Lecture 15: Dimethyl Ether, Sn2 Reaction, Ethyl Acetate
Document Summary
Reminder: key aspects of the sn2 reaction discussed on oct 2nd: Summary of the meeting of oct 11 red: lobes of the *c x. + x the following four requirements must all be satisfied for a substitution reaction to occur in the sn2 mode: the structure of c x must permit facile access to the c-lobe of the * As a consequence of the above, one observes the following: Sn2 reaction, no matter how strong the driving force for the substitution process might be. Suppose that one attempted an sn2 reaction between the enolate of an ester, e. g. , ethyl acetate, and dimethyl ether according to the following equation: Whereas the basicity of the medium drops considerably in the course of this hypothetical process, therefore there is definitely a thermodynamic driving force for it, the leaving group fails to satisfy the above requirement. O pka of conj. acid (ester) 25 stronger base.
