Retrosynthetic analysis problems Organic Chemistry II Dr.

Kamil Makowski
1. How would you make these four compounds? Give your disconnections, explain why you
chose them and then give reagents for the synthesis
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
2. Following two compounds was tried to obtain unsuccessfully in bellowed conditions. Tell
what’s went wrong. Then try to find a solution.
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski

a. Suggest reagents for each step.

b. Draw the retrosynthetic analysis giving the disconnections that you consider the
planners may have used and label them suitably.
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
4. Show how the relationship between the alkene and the carboxylic acid influences your
suggestions for a synthesis of these three compounds.
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
5. How would you make these compounds?
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
6. Show how the relationship between the two carbonyl groups influences your choice of
disconnection when you design a synthesis for each of these ketones
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski

7. Perform the retrosynthetic analysis of the following compound. Remember, your planned
synthesis must be synthetically possible and shouldn’t suffer from regio- or chemoselectivity
issues.
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
8. How would you synthesise those compounds?
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski
9. How would you make those two compounds using Grignard reaction for C-C bond formation?

10. How would you make this compound via enamine intermediate?
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski

11. Consider using protecting groups to prepare those two compounds:

12. How would you convert this nitro compound into the two products?

13. How would you convert this diamine to either of those two protected derivatives?
Retrosynthetic analysis problems Organic Chemistry II Dr.
Kamil Makowski

14. How would you obtain the following final product using reagents show on the scheme?
Consider using protecting groups.