[davidenarb]

Hi all,

I am in organic chemistry undergraduate. I would like to organize a toolbox of reactions. This is my plan, and I would like to here your opinions and suggestions before starting doing so.

-Organizing the reactions by the type of functional group (Preparation of Alcohols, Alkenes, ...etc)
-Highlight streochemistry and regiochemistry if applicable 
- I didn't decide if i will write the mechanisms as well.

What should I consider or remove, on top of that?

Also, is it important to write every reaction covered in the textbook?

Thank you

[kriggy]

1) I think the best way is to sort by functional groups and then by stereochemistry, IMO its the fastest way to find reaction you need. Mechanisms are usefull but I dont think its needed. Maybe in some cases.

2) It depends. Are the reaction in textbook stil usefull? Arent there for example better options?

[davidenarb]

1) I think the best way is to sort by functional groups and then by stereochemistry, IMO its the fastest way to find reaction you need. Mechanisms are usefull but I dont think its needed. Maybe in some cases.

2) It depends. Are the reaction in textbook stil usefull? Arent there for example better options?

what do you mean by " I think the best way is to sort by functional groups AND THEN by stereochemistry". are you suggesting writing two reactions for one reaction?  I cannot understand your idea 

can you give an example

[kriggy]

For example, you start with organizing reactions by functional groups and for each functional group, you organize the reactions by other criteria, could it by regiochemistry or price of reagents or whatever criteria you want. I probably didns express my thought well.

[davidenarb]

For example, you start with organizing reactions by functional groups and for each functional group, you organize the reactions by other criteria, could it by regiochemistry or price of reagents or whatever criteria you want. I probably didns express my thought well.

Thank you

[orgopete]

I'd agree with functional group first. If you know your target, it will undoubtedly contain some functional group transformation.

Then I'd the go by reaction mechanism. If you were making a alcohol, I'd find it logical to look at reduction reactions separately from reactions of aldehydes, ketones or from alkenes, for example. Also think umpolung.

I never worried too much about stereochemistry. I generally thought that for every reaction that gave one isomer, there would be another reaction that gave the opposite isomer. Because I was in the area of chemistry in which a lot of chemistry involved aromatic rings, regiochemistry was more important. Using a different chiral ligand is not going to reverse the course of a reaction. None the less, I wouldn't organize about regiochemistry per se. I'd stick with mechanism.

I was in chemical discovery. It may be interesting to hear what Disco would say as he was more involved in large scale syntheses.

[discodermolide]

Well I was also in discovery and we just looked for the quickest way to make any given compound within the scope of the SAR, it did not bother us how we got there.
In development it was different, there you are really concerned with the functional group chemistry in terms of mechanism and reaction safety. .
I think what the OP wants to do has already been done in the Houben-Wheyl series or Barton's Comprehensive functional group transformations.
However, there is no substitute for reading the literature, by all means make a little card file index or an electronic database of reactions (to be more up to date), reagents cross-referenced with functional groups. But read the literature, and don't stop. Make yourself a list of relevant journals and make sure you glance through each issue, most have a TOC and you can see what interests you.
Enjoy.

[zsinger]

Do yourself a favor and learn about the word "synthon".  It was developed by E.J. Corey as a way to describe synthetic cationic and anion equivalents of a needed piece of a molecule, with given reagents.  Do a google search for a list of synthons, and if you can't find one, I have one that I can give you.  They will help you to understand how much of this electron pushing business works!  Best.
          -Zack