COLLEGE OF LIBERAL ARTS AND SCIENCE
ORGANIC CHEMISTRY LEARNING RESOURCES @   the Department of Chemistry and Biochemistry

Teach Yourself Retrosynthesis Problems

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You are required to be able to do simple retrosynthesis. The idea is to see if you can put together individual chemistry facts you have learned to do something useful. Synthesis is an important part of organic chemistry. These problems develop valuable thinking skills that are broadly useful. Retrosynthesis is hard because you need to know BOTH the reactions, and how to solve the problems themselves. You will improve both by practice. Given below is a suggested procedure to solve these kinds of problems

Suggested Procedure 1 Except in simple cases, start from the product and work backwards (RETROsynthesis) 2 Look for the "skeleton" of the starting material in the product. Determine which C-C bonds have to be made. Look for C-C bonds close to functional groups, there are very few ways to simply put a C-C bond in the middle of an alkane chain 3 Summarize the functional group interconversions (FGI's) you need to do 4 Decide whether you will do a functional group transformation or do a C-C bond forming reaction (if required) first. Focus your attention on the C-C bond-forming reactions first. If you can't do one, then try a FGI. Specifically, if there is no suitable functional group close to a C-C bond you want to then put one there to help with the C-C bond reaction 5 Now you have a new compound to work back from. Go back to step number 2. Your procedure may not be going in the right direction, be prepared to repeat some of the steps in a different way, including the first one!

Practice Problems Your primary resource for practice problems is The ASU RETROSYNTHESIS Teaching Web Site The second resource are those problems summarized in the Table below. They are given in terms of the most recent functional group involved. There will often be more than one way of doing most of these problems and the answers represent only one solution. In some cases the answers may not be the best solution, but they illustrate a principle or are the only way of solving the problem with the information to date. In addition, you could use other reactions not covered in our courses. The problems here represent a range of difficulty from easy to challenging.
Alkyl Halides/Alkenes Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8 Problem 9  Answer 9	Alkynes Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5
Alcohols Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8 Problem 9  Answer 9 Problem 10  Answer 10 Problem 11  Answer 11	Ethers/Epoxides Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4
Conjugated Systems Problem 1  Answer 1	Aromatic Systems Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8 Problem 9  Answer 9 Problem 10  Answer 10
Aldehydes & Ketones Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3	Enols/Enolates Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8
Carboxylic Acids and Derivatives Solved Problem    See The Solution  Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8 Problem 9  Answer 9 Problem 10  Answer 10	Amines Solved Problem    See The Solution  Problem 1  Answer 1 Problem 2  Answer 2 Problem 3  Answer 3 Problem 4  Answer 4 Problem 5  Answer 5 Problem 6  Answer 6 Problem 7  Answer 7 Problem 8  Answer 8 Problem 9  Answer 9 Problem 10  Answer 10

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