Talk:Solvolysis

SN1?[edit]

Need solvolysis always be an SN1? Why can't it be an SN2? This is a terribly brief article, and the context seems to be missing. I've pointed ammonolysis and alcoholysis here. --Rifleman 82 05:31, 12 October 2007 (UTC)[reply]

Transesterification is Sn2. I've tried to find suitable sources to back this known, but I've only come up with these links and the word a few professional biodiesel chemists (obviously not sufficient): http://www.sn2.com.au/about.php http://www.biodieseltechnologiesindia.com/pro&tech.html . Neither March's Advanced O-Chem or Guidebook to Mechanism specify either. I'm under the impression that the need for strong catalysts is evidence of the SN2 nature of the reaction.--E8 (talk) 01:01, 24 September 2008 (UTC)[reply]

After further investigation, Sykes's A Guidebook to Mechanism in Organic Chemistry, 6th Edition, states that the transesterification mechanism is B_AC2 (Based-catalyzed, acyl-oxygen cleavage, bimolecular). Source page #239.--E8 (talk) 14:33, 24 September 2008 (UTC)[reply]

Not necessarily, as transesterification can also be catalyzed by an acid. But it is usually neither SN1 nor SN2 because the reaction involves addition to the carbonyl. --Itub (talk) 15:15, 25 September 2008 (UTC)[reply]

Yes, I should've mentioned that. This discussion has taken place over a number of different pages for the last year. Do have access to kinetics data that would indicate what type of pathway acid-catalyzed transesterification follows?--E8 (talk) 15:43, 26 September 2008 (UTC)[reply]