Talk:Aldol reaction

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Archive 1 ( - Feb 2006)

[edit] Revisions

Hey guys, I have a little time to work on this article again...I'm open for suggestions. I was going to add a bit on the newer organocatalytic and catalytic, asymmetric methods, plus some stuff on thiazolodinethione auxiliaries. Any ideas? It's a pretty big article already. What do we need to do to get it to "featured article" level? Eugene Kwan 16:30, 24 November 2006 (UTC)

  • Hi Eugene, welcome back, I haven't changed my view on this article since the last time (see my notes somewhere in the text above) but the article should be considered for featured article as it is. I am having some problems though with your use of syn and anti with respect to linear aliphatic chains in the text V8rik 17:39, 24 November 2006 (UTC)

OK, sure...thanks. What problems are you referring to? Are they mentioned above? Eugene Kwan 04:33, 25 November 2006 (UTC)

    • they are in this part. There was some unfinished discussion on what the average Wiki reader is and I maintain that you cannot expect the average reader to have any knowledge on the Aldol reaction. On the other hand you can simply direct to other articles when thing are unclear. One example: if the reader is unfamiliar with nucleophilic addition you simple link it in the text as nucleophilic addition, a reader already familiar with nucleophilic addition can skip it and read on. If you go for FA status non-chemists will review the article and I am sure you will get questions on unclear technical terms. I have already taken care of stereoinduction and allylic strain but other unexplained terms remain V8rik 18:25, 25 November 2006 (UTC)
  • This reaction is a standard part of the second-semester syllabus in most US introductory undergraduate organic chem courses, so probably many thousands of students check this page (mostly around April, when it is usually taught). These students should know the basics of organic chemistry, including basic carbonyl chemistry, but many will probably be unfamiliar with terms like regiochemistry, stereoselectivity, asymmetric induction, kinetic vs. thermodynamic products. They should hear in class about use LDA and alkoxide bases (no others!), dehydration, and the problem of control in crossed aldols. In the UK it's probably similar, but may go a little deeper (e.g. kinetic vs thermodynamic enolates). I also cover the reaction in more detail in my advanced organic class - a much smaller number of students take this - and for that course the more advanced coverage in this article (E/Z enolates, Evans, etc.) is excellent. I hope this provides some guidance on what I'd guess the "average" reader of this page could be expected to know. Walkerma 06:22, 26 November 2006 (UTC)

OK, I'll tell you what. I'll let you guys figure out what sort of editing to do, and I'll just add some more material. I am a bit concerned about the length of this article, however. Any thoughts? Eugene Kwan 22:29, 26 November 2006 (UTC)

I've added a lot of new material, and am still in the process of finishing it. Please let me know what you think. Eugene Kwan 23:22, 27 November 2006 (UTC)

[edit] Introduction

I would vote for

The aldol reaction is an important method for forming carbon-carbon bonds

instead of "constructing". One constructs the skeleton of a molecule, or perhaps even the stereochemistry around a particularly difficult center, but a simple carbon-carbon bond is just "formed".

Also, I'm not really in favor or "naturally occurring molecules". "Natural products" is what the total synthesis folks synthesize, and using any other word is imprecise language and talking down to the readership. They deserve better. Dr Zak 22:09, 7 December 2006 (UTC)

It should also be pointed out that two stereocenters are set up in one reaction step, it's a salient feature. Dr Zak 22:28, 7 December 2006 (UTC)

I agree, especially with using forming instead of constructing. These are always called bond formation reactions in my experience. Maybe the idea was to avoid the funny-sounding "for forming", but that could be avoided by rephrasing. Maybe "The aldol reaction is an important carbon-carbon bond formation reaction", or "The aldol reaction is an important method for the formation of carbon-carbon bonds". Itub 23:34, 7 December 2006 (UTC)
OK, agreed. I just thought the ordinary person would not have the terms "natural product" or "bond formation" in their vocabulary. It's a tough job. What's the FA status? Will it just sit on the FA nominees list forever? Also, I felt thalidomide was a bad example, since the enantiomers interconvert in the body. Eugene Kwan 03:36, 8 December 2006 (UTC)
Amen, brother, on the thalidomide. Plus it's not an aldol adduct either. By the way, shouldn't it read "multigram-scale quantities of the drug" near the end of the first paragraph? Dr Zak 03:43, 8 December 2006 (UTC)
Yes, that works too. Eugene Kwan 00:06, 9 December 2006 (UTC)

Hey, this is great! Good work, everyone! A note about chemistry images: PNG looks fine, but there's a big problem with getting all the images to look the same size. It looks really weird with all the structures being different sizes. So I don't like PNG for the structures. Anyways, if you guys see any more errors, please, let me know! Eugene Kwan 05:57, 9 December 2006 (UTC)

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