CHEM 35 Chapter Notes - Chapter 13: Alpha And Beta Carbon, Diethyl Malonate, Acetoacetic Acid

• School: Stanford University
• Department: Chemistry
• Course: CHEM 35
• Professor: Du Bois

Document Summary

Klein enolates and enols: alpha protons, alpha protons somewhat acidic, generates fairly reactive anion (enolate, keto-enol tautomerism a. Oh group: ketone and enol are in equilibrium, tautomers = molecules that differ in only just placement of proton c. i. Not same as resonance; 2 different compounds: usually equilibrium favors ketone, aromatic situation, favors enol f. Remove proton = negatively charged intermediate f. ii. f. iii. Introduce proton: can"t be intramolecular because too far, acidic conditions h. i. Never use oh- and h3o+ in same reaction i. ii. Small amount enol will attack electrophile and convert d. ii. Keto-enol equilibrium re-established by producing more enol until all ketone converts: put halogen at alpha position e. i. Ketone treated with br2 in aqueous acid to make alpha- halo ketone e. iii. Acetic acid may be used as reagent (too slow to react carboxylic acid with halogen) f. To put halogen at alpha of carboxylic acid f. i. Get rid of oh and then replace f. ii.