Here is some Nucleophilic Aromatic Substitution for ya!

Are sure you have the correctย organic chemistry question?

I know…I know…nucleophilic aromatic substitution doesn’t sound right. You learned that you can’t doย 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 aromatics๐ŸŒน๐Ÿฅ€๐Ÿ’๐ŸŒผ๐ŸŒบ๐ŸŒธ!! ๐Ÿ˜€. Perfect for spring time, right ๐Ÿ˜‚๐Ÿคฃ๐Ÿ˜‚?

OK – so…if we take this substituted benzene…and add sodium methoxide (NaOCH3), what do you think we will get๐Ÿค”?

A, B or C?

Yes…I ๐Ÿ‘€ you in the back raising your hand ๐Ÿคš… let’s see what you got!!

Alright, let’s get to it ๐Ÿ‘๐Ÿ‘Š๐Ÿ’ฅ!

Let’s look at the answer…

And….here it isย ๐Ÿ™‚๐Ÿ™ƒ๐Ÿ™‚๐Ÿ˜€! 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….๐Ÿ’ฅ!

The ring is vulnerable ๐Ÿ˜‚๐Ÿคฃ๐Ÿ˜‚!

So, theย OCH3ย 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…๐Ÿฅ‹.

Strange huh ๐Ÿค”?

I know…but it happens ๐Ÿ˜ฎ๐Ÿ˜€. Nice work everyone!! Keep bringin’ your OChem skills ๐Ÿ‘๐Ÿ‘Š๐Ÿ’ฅ!

And if you are looking to see this in a video…

Well, I just happen to have one!

Leave a Reply

Your email address will not be published. Required fields are marked *