Are sure you have the correct organic chemistry question?
I know…I know…nucleophilic aromatic substitution doesn’t sound right. You learned that you can’t do SN2 reactions on sp2-hybridized atoms.
However, I assure you, it does work
We just have to take a “detour” in the mechanisms before we actually substitute
So, let’s start with the question I posed on Instagram today…
Well…up next? More aromatics🌹🥀💐🌼🌺🌸!! 😀. Perfect for spring time, right 😂🤣😂?
OK – so…if we take this substituted benzene…and add sodium methoxide (NaOCH3), what do you think we will get🤔?
A, B or C?
Yes…I 👀 you in the back raising your hand 🤚… let’s see what you got!!
Alright, let’s get to it 👍👊💥!
Let’s look at the answer…
And….here it is 🙂🙃🙂😀! I know I gave it away in the title, but…
It is nucleophilic aromatic substitution.
With the fluorine AND the nitro group on the benzene, it is super deprived of electron density. Therefore, something can attack….💥!
The ring is vulnerable 😂🤣😂!
So, the – OCH3 attacks at the carbon with the fluorine. Then, the electrons can move all the way to the vacuum cleaner (nitro group).
And finally, the electrons move back through the pi-system and kick out the fluorine…🥋.
Strange huh 🤔?
I know…but it happens 😮😀. Nice work everyone!! Keep bringin’ your OChem skills 👍👊💥!
And if you are looking to see this in a video…
Well, I just happen to have one!