Welcome to Organic Chemistry Problems!

 

This web page is intended to be a resource for students, instructors, and practitioners of organic synthesis. Primarily, this resource is intended to provide extra example problems for students at the introductory graduate student level (i.e. first year graduate students who are in an organic synthesis course who have prior experience with organic chemistry) or advanced undergraduate level.  The provided problems are intended to cover a number of key concepts including complex arrow pushing mechanisms, diastereoselective synthesis, and the uses of common reagents. This web page IS NOT intended to be a repository of named reactions, total syntheses, or reagents. Other such resources exist and links are provided to them on “external links” page. There are a number of features of this page that you may find useful.

 

Reaction Problems

The Additions, Reactions on Rings, and Other tabs serve contain the questions for the “quiz” portion for students who would like to work through the problem in detail on their own. Several variety of questions can be accessed by clicking on the title on the top of the page or by scrolling through the examples. The general question is to determine the product of the reaction(s) - including stereochemistry. For ease, questions are categorized by the functional group or motif undergoing the reaction. For most of these reactions, an established predictive model exists, such as A1,3 strain, Felkin-Ahn model, Cram’s chelation control model, directing group effects, or concave-convex differentiation. Alternatively, a number of reactions are provided with the corresponding product and students can attempt to provide a reasonable arrow pushing mechanism by which the product could be formed. The final class of questions provides students with a starting material and a sequence of common reagents/reactions. Students can attempt to predict the product of each subsequent step of these common synthetic reactions in a “road map” style, similar to what would appear in a journal article.

Reaction Answers

Answers are provided for all of the reactions can be found by clicking on the question's image. Each product is drawn with a predictive model that could be used to rationalize the formation of that compound. The primary reference containing the reaction is linked and can be accessed by clicking “Reference”. One additional feature that will likely be useful for instructors or practitioners is that the ChemDraw file is freely accessible and can be downloaded by clicking on “ChemDraw” and then the “download” button from the pop up page.

External Links

A number of wonderful web sites already have repositories for total syntheses, named reactions, reagents, or other information. Links to a wide range of organic chemistry related sites are provided on this page.

Contact Info

If you find an error, typo, or have other questions or comments about the site, please contact organicchemproblems@gmail.com. If you would like to submit a reaction, sequence, or mechanism please do so to the same email.  All that is needed is your name and a chem draw file containing the full sequence, DOI of the primary source, and your name (so that we can add “contributed by ____” to the file). Please keep in mind that the problems are intended for first year graduate students. Obscure reagents, unduly complex mechanisms, or reactions involving multiple predictive models will not be suitable for this audience. That is about it! Please enjoy the site and all of the wonders and challenges that organic synthesis has to offer!