I was told in this question: https://chemistry.stackexchange.com/questions/4789/synthesizability-and-energy-minimization-of-a-structure/4791#4791 to

[Count the] "number of accessible functional groups (alkenes, amines, alcohols, esters, etc) which make it easier to prepare, 5) number of inaccessible functional groups (aromatic rings, polycyclic systems, quaternary carbons, complex or long alkyl groups),"

But when I googled accessible functional groups and inaccessible functional groups no pages had a longer list. I found a SMARTS file which lists some common functional groups. Could someone help me determine which are readily synthesizable?

Thank you


What you are asking amounts to the collected knowledge, wisdom, and intuition of the organic chemistry community. Your best bet will be to find an organic chemist, preferably one with a graduate degree, to work with you on this project. Said organic chemist can apply his/her knowledge/wisdom/intuition to each functional group in less time than it would take you to look up the answer. Doing so frees you to work on the algorithm you describe in your other question.

The beginning of the answer to this question takes me two semesters to get through with my introductory organic chemistry students, and that is just for the common functional groups. After covering the basics of organic structure and reactivity, most texts have 15-20 chapters organized by functional group containing the reactions of and syntheses of said functional groups.

The common functional groups covered in most introductory sequences:

  • alkanes
  • cycloalkanes
  • alkyl halides
  • alkenes
  • conjugated dienes and other unsaturated systems
  • alkynes
  • aromatic ring systems
  • alcohols
  • glycols and other diols
  • phenols
  • ethers
  • epoxides
  • aldehydes
  • ketones
  • carboxylic acids
  • esters
  • anhydrides
  • acyl halides
  • amides
  • amines
  • nitriles
  • thiols
  • sulfides
  • acetals
  • imines
  • enamines
  • heterocycles
  • nitro compounds
  • diazo compounds
  • carbohydrates
  • amino acids
  • nucleic acids

If you want to know about every functional group, you will need an advanced, probably graduate level, synthesis course. However, even I have not heard of some of the designations on your list, like semithiocarbazide.

Some good ideas on where to start, if you choose not to consult with an organic chemist.

  1. Check an undergraduate level organic chemistry book out of your local library and get some sense of the subject. In your case, it does not look like you need to know how the reactions work, just that they exist, so you can use the text as a reference source.
  2. Sign up for a free MOOC in organic chemistry. Again, you just want to know that the reactions exist, so you can pick and choose the content from the course.
  3. Acquire a copy of one of the seminal books in organic chemistry, March's Advanced Organic Chemistry. This book is not for the fainthearted but it gives good treatment to the functional groups, including the less common ones.
  4. Find (do not buy - these books are not worth the price tag) a copy of either Comprehensive Organic Transformations: A Guide to Functional Group Preparation by Richard Larock (which is now 14 years old) or the set of Comprehensive Organic Functional Group Transformations, which appears to be many volumes (now 9-10 years old).