Future Experts come here and share their knowledge base and concepts with each other. Every article submitted is reviewed by experts. Nickels are awarded to articles in terms of authenticity, relevance, clarity and presentation.
Pinacol itself is produced by magnesium reduction of acetone, probably by way of a ketyl intermediate. Since the diol is symmetrical, protonation and loss of water takes place with equal probability at either hydroxyl group. The resulting 3ยบ-carbocation is relatively stable, and has been shown to return to pinacol by reaction in the presence of isotopically labeled water. A 1,2-methyl shift generates an even more stable carbocation in which the charge is delocalized by heteroatom resonance. Indeed, this new cation is simply the conjugate acid of the ketone pinacolone, which is the product of repeated rearrangements catalyzed by proton transfer. Each step in this rea
more ...
submitted by magiclko (4210 m) on 10 Mar 2007 17:27:27 IST (5 comments 338 views)
