18.7 Retrosynthesis with Aromatic Compounds | Organic Chemistry

[@jashanpreetkaur6397]

I WANT TO THANK YOU CHAD TO BE SUCH A HUMBLE SOUL, YOU HAVE PUT SO MUCH EFFORTS INTO THESE LECTURE ANNND PROVIDED THEM FOR FREE, I SALUTE TEACHERS LIKE YOU IN THE WORLD WHERE EDUCATION HAS BECOME AN EXCHANGE OF CAPITAL.... RESPECTTT !!!!

[@ChadsPrep]

Thank you for the kind words and I am happy to hear that you like the videos

[@namhlamadlala321]

Oh Chad!!!I owe you a million when i get a job!🥰

[@ChadsPrep]

Woo woo! All the best in your future employment endeavors!

[@neveenbotros3257]

Best professor ever!

[@ChadsPrep]

Thanks!

[@erikkirakosyan8011]

Thank you again !!

[@ChadsPrep]

You are welcome, Erik!

[@alya410]

At 14:48 you did a synthesis question where you have used SO3, H2SO4 and then HNO3, H2SO4. Wouldnt the sulfuric acid in the nitric acid act in a way to remove the SO3 on your benzene (unwanted side reaction)? If not, then I noticed that later on you use dilute sulfuric acid to remove SO3 so sounds like that might occur.

[@hosseinrm9642]

Fantastic thanks man!

[@ChadsPrep]

You're welcome and Thank You.

[@strugglingcollegestudent]

5:00 won't the carbocation rearrange since this is alkylation not acylation?

[@Patriots4890]

it is a primary chlorine therefore there wouldn't be any rearrangement

[@s.p.8508]

Why does’t the sulfonate group block the acylation from happening at 3:52 ?

[@ChadsPrep]

Hey SP! The para position is blocked by the sulfonate which is why it directs ortho

[@s.p.8508]

@@ChadsPrep but doesn’t a sulfonate group block additional friedel-crafts reactions from happening?

[@ChadsPrep]

@@s.p.8508 Hello S.P.! You might very well be right. Friedel-Crafts reactions don't work on strongly deactivated rings. If the only substituent were the sulfonate group then you could conclude that the reaction wouldn't be possible. But the alkyl group is an activating group and likely counters the deactivating nature of the sulfonate group. But then you can factor in some steric issues. Acyl groups are large and here we're trying to force it to go ortho to an alkyl group. So now we have a confluence of factors which lead us to believe that the yield might not be as good as we'd like if we were to perform this reaction in the lab. You've convinced me to use a different example for the next go around of the ochem playlist (probably a couple years away). Thanks!

[@s.p.8508]

@@ChadsPrep alright, thank you!

[@saifullah-ss3yr]

Great 😍

[@ChadsPrep]

Thx!