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By James Ashenhurst

350 Examples of Classic Org 1/Org 2 Reactions From “Organic Syntheses”

Last updated: May 13th, 2021 |

If you are an instructor and prefer to source your exam questions to the original literature, Organic Syntheses [1] is a great source of classic, “real life” examples of commonly taught reactions like the Claisen condensation, Clemmensen reduction, Fischer esterification and many more.

From the first 6 Collected Volumes there are plenty of instructive examples that could be useful as potential exam questions or procedures for lab courses.

A collection of about 350 Chemdrawed reactions from Org Syn (with references) that contain such “classic” reactions is available on the MOC Flickr:

https://www.flickr.com/photos/182129490@N06/collections

The set of 350 .CDX files can be downloaded here for free, along with an XLS that contains the DOIs.

Here are just a few examples.

Double addition of phenyl Grignard to an ester 

A Clemmensen reduction (which doesn’t touch the carboxylic acid) (Org Syn. Coll. Vol. 2,  p. 499)

A classic Claisen condensation (Org. Syn. Coll. Vol 3. p. 17

It’s one thing to make reactions up for a test (and of course necessary from time to time) ; it’s even more instructive to be able to tie  that specific reaction back to a literature procedure, complete with experimental details, yield, and so on.

This was a fun project and I want to share it with instructors or anyone else who might find these procedures useful for teaching purposes. Thanks to Nick for assistance with the drawings.


[1] If you’re not familiar with Org Syn, it’s one of the only examples of a “peer-review plusjournal: articles are published only if they survive both peer review and successful replication by an independent team of researchers using the provided experimental procedure.  It’s the gold standard of organic chemistry preparations.

As my old boss used to say, “If you can’t get an Org. Syn. prep to work, it’s *your* fault.”

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