Gabriel Synthesis Reaction Mechanism - Alkyl Halide to Primary Amine

This organic chemistry video tutorial provides 2 versions of the mechanism of the gabriel synthesis reaction which converts alkyl halides into primary amines. It uses phthalamide as the starting material which has an imide functional group. A strong base such as KOH is used to activate the imide by deprotonation followed by an SN2 backside attack of the nitrogen on the alkyl halide. If Hydrazine is used in the third step, the side product will be Phthalimide Hydrazide. If acid hydrolysis H2O / HCl is used in the third, Phthalic acid will be produced instead.

[@twistidbow3594]

Just stopping by to say you're awesome. Your mechanisms are always very complete and you explain why each step happens, its easy to follow and understand. You deserve more views!

[@aamalrahim5597]

Justin Kwon I totally agree. He deserves more views and likes. I'm a subby!

[@zacharias1567]

love your videos! not to quick, and not too slow. Definitely a huge lifesaver in orgo 2. Thanks so much!

[@bernhardkmakanga6317]

All I want is your name. I want to search you up😭😭😭. You've been my saviour ever since

[@edmhouse5273]

julio gonzales

[@wylona2494]

Omg I sincerely hope my professor doesn't want me to draw this monster. Both in class AND in my book, the whole mechanism was skipped over. they did the first few steps and then was just like "tadaah!" lol. So I came here to find the whole mechanism and now I see why they skipped so much of it....

[@Rana-ur5tu]

Yeah same

[@gabym4218]

so true

[@kkhanthony8533]

I wanna die from this but i know i am gonna die so peacefully :) thx ya :D

[@chiramana_]

Thank you so much 🙏🏻

[@stevesalehi2095]

you're the best tutor ever. thanks

[@mrcoolest1]

Love you sir from India

[@EmptySequencee]

I am still struggling with this synthesis and it is driving me nuts! Way too many arrows and steps! There must be a quick and dirty method! :-(. I don't want to memorize mechanisms... I want to actually know what it is I am doing.

[@lovecatz101]

Great explanations to each arrow of the mechanism - thanks!

[@alicecho261]

I don't know if you already knew and edited in the recent video, but the movement of electrons of the intermediate where hydroxy group electrons collapse back is not correct. Not the double bond but the nitrogen should pick up the hydrogen so double bond's electron should be pushed to the nitrogen and that nitrogen should pick up the hydrogen. If a double bond directly pick up the electron, you won't have a neutral nitrogen with a new hydrogen added.

[@ICavalcadeI]

before adding base, would the amine precipitate out of the reaction as a salt? That would make things a thousand times easier to handle in the subsequent reaction I'd like to perform.

[@madisonking8057]

Are you synthesizing drugs?

[@dobbysurfs]

10:15 I didn't understand from that part. There is only 4 carbon rings Plz explain

[@javiersevilla8790]

Muchísimas gracias Bro! Saludos desde México. Thank you so much!! Your videos are awesome and well explained, greetings from Mexico

[@jonathansanchez8802]

KING

[@alberteinstien7016]

Superb bro

[@harihus8122]

8:52

[@patrycjaprzedwojska1072]

loved the video, hated the reaction 😢

[@harihus8122]

18:17

[@osotypical5238]

too much stress

[@gabrieltru2409]

yoooooooooooooooooooooo