# Functional Group compatibility in organic chemistry [closed]

As a continuation to the question:
Predicting reaction among compounds

I found the list of functional group on wikipaedia:
https://en.wikibooks.org/wiki/Organic_Chemistry/Overview_of_Functional_Groups

Now in the previously mentioned question, I got a clue that if the functional groups are compatible then reaction can occur, can you please tell me which are compatible with which?

## closed as too broad by Loong♦, user15489, M.A.R. ಠ_ಠ, Ben Norris, WildcatJul 11 '15 at 13:19

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

• I realize that you're genuinely curious; but as for the downvotes, I can understand them. This question is far too broad. It can't be answered with 100 books. – M.A.R. ಠ_ಠ Jul 11 '15 at 8:29
• so there is no such compatibility rule? – girl101 Jul 11 '15 at 8:36
• There is no such compatibility. It's different from what you think. You might search for how chemists go about explaining reaction mechanisms in organic chemistry; terms like nucleophile, electrophile, leaving group, addition etc. – M.A.R. ಠ_ಠ Jul 11 '15 at 8:47
• Being a computer scientist you would better stop "getting clues" on how things work in chemistry because your clues will likely be wrong. Just ask what actually you want to do and we will tell you is it even possible in the first place or not. – Wildcat Jul 11 '15 at 13:31
• Four of your six questions have been closed, some of them with a negative score. The system will notice that and if you continue to ask these kinds of questions, and get closed/downvoted, you will likely run into a block/ban again. – Martin - マーチン Jul 12 '15 at 5:09

As I mentioned in my answer to this question, you are asking for something about which my two-semester organic chemistry course sequence just scratches the surface.

After covering the basics of organic structure and reactivity, most introductory organic chemistry texts have 15-20 chapters organized by functional group containing the reactions of and syntheses of said functional groups

In some cases, we can be reasonably certain that two functional groups will always react (primary amines and acyl halides), but in many, many other cases additional reagents, conditions, catalysts, etc. are needed. Different reagents and conditions can cause different outcomes from the same combination of reactants.

Here is a short sample of what I mean from among the earliest reactions we tend to study in the first semester organic chemistry course.

Alcohol + alkyl halide

In most cases, this combination of compounds will not amount to much, but there are some special cases:

• Tertiary halides in primary alcohols undergo solvolysis

$$\ce{(CH3)3CBr + CH3CH2OH -> (CH3)3COCH2CH3 + HBr}$$

• Addition of strong base promotes elimination in any alkyl halide, especially with heat.

$$\ce{CH3CH2CH2Cl + KOCH2CH3 ->[\ce{CH3CH2OH}][\Delta] CH3CH=CH2 + KCl + HOCH2CH3}$$

• The major regioisomeric product can be controlled by which base is present. $$\ce{CH3CH(Cl)CH2CH3 +NaOCH2CH3 ->[\ce{CH3CH2OH}][\Delta] CH3CH=CHCH3 + NaCl + HOCH2CH3}$$ $$\ce{CH3CH(Cl)CH2CH3 +KOC(CH3)3->[\ce{(CH3)3COH}][\Delta] CH2=CHCH2CH3 + KCl + (CH3)3COH}$$

If we take our primary alkyl halide and strong base, but the reaction is in DMSO (dimethylsulfoxide) instead of ethanol, and the reaction is kept cold, subsitution prevails.

$$\ce{CH3CH2CH2Br + NaOCH2CH3 ->[\ce{DMSO}] CH3CH2CH2OCH2CH3 + NaBr}$$

The reaction space in organic chemistry is very large and, while functional group analysis is always a good place to start learning, the effects of reagents and conditions, sterics and conformation, and other factors are also important. Rather than ask a question here that has an answer that amounts to whole textbooks worth of information, maybe you should sign up for a free MOOC on organic chemistry. That will give you a sense of what types of things are and are not possible (as per M.A.Ramezani's comment), and then you can ask more focused questions here.