CHM247H1 Chapter Notes - Chapter 22: Command And Control, Diethyl Malonate, Enamine
Document Summary
The position next to a point of reference is the alpha ( ) position. An electrophile (e+) can be substituted for an h. Tautomers the spontaneous interconversion between two isomers; usually with the change in position of a hydrogen: keto and enol isomers are tautomers. Tautomers vs. isomers: tautomers constitutional isomers; different compounds with different structures. Have atoms arranged differently: resonance forms different representations of a single compound. Differ only in position of and non-bonding electrons. The reaction proceeds by way of: electron rich intermediates form new c-c bond with e, enol is more electron rich than alkene, because oh has a powerful electron donating resonance effect. In -dicarbonyl compounds the enol form predominates: the enol form is stabilized by conjugation and intermolecular hydrogen bonding, especially as a 6- membered ring. Acid catalyzed enol formation: protonation occurs first forms a resonance stabilized carbocation, the proton is them removed forms the enol.
