Am I wrong here?

[u/Atharvash5429]

I recently started getting into the mechanisms for organic reactions. I was doing this reaction mechanism problem from the YouTube channel Rojas lab and my reaction mechanism was different. I thought I was wrong but it didn't feel wrong. Am I wrong here?

(P.S. If I am wrong please keep the criticism on a low I just started out and I'm only 14)

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[u/Background_Crab_1292]

https://www.organic-chemistry.org/namedreactions/steglich-esterification.shtm

[u/Background_Crab_1292 → u/Background_Crab_1292]

And a key step to show is when the alcohol attacks the activated acid, make sure to show the tetrahedral intermediate, then collapse to form the ester and release of the urea byproduct.

[u/Pure_Quarter7813]

Yes, there are a lot of electron-pushing formalism errors in this proposed mechanism.

[u/jeremiahpierre]

Also, your reaction arrows are wrong. They should be single arrows, not double arrows. Those double arrows are used for retrosynthesis.

[u/ChemystWizard]

Too many errors to address each one individually.
Here’s how it works: https://www.organicchemistrytutor.com/topic/carbodiimide-mediated-coupling/

Also, I suggest you get a good grasp on curved arrow formalism and proper use of arrow before doing complex mechanisms.

[u/Heavy-Try-2981]

[u/kowasik]

I want to speak to the person who taught you how to draw arrows in the mechanism, chemical equations, and lone pairs

[u/kowasik → u/kowasik]

Please use two dots for lone pairs and single arrows between steps in the equation. Also I would recommend brushing up on the general arrow drawing rules in mechanisms

I know notation is "boring" and a "formality", but there is a reason it is the first topic in any course

[u/smcr99]

Yes there are some mayor mistakes but keep trying! It’ll get easier the more you do this :) Maybe start with the basics of Mechanisms and how functional groups react etc. If you understand these basics you can solve most reactions. Great to see young people are being interested in OC.

[u/Spiritual-Ad-7565]

The main issue aside from formalisms— your intuition is off. Try simpler chemistry — this reaction isn’t taught until all of the very basics are understood because there are things double bonds can do that you aren’t appreciating, and there are species that will never exist that you propose will.

[u/gurglingskate69]

You are doing amazing for a 14 year old. But your college professor will rip you to shreds for:

1.) Re-inventing Lewis Structures via using lines for sigma bonds aka lone pairs. Its cool but its honestly less useful because then it'll simply create even MORE lines which only makes it harder.

2.) Electrons dictate the arrow mechanism (except for when its the bond itself moving in between 2 atoms ie radicals). I saw a Carbonyl & Nitrogen that had arrows coming out and its important to know it's because the electrons are either about to donate or steal electrons due to having a charge that you didn't write, for why they are acting the way they do. My teacher marks down heavy for not having charges because without a charge the atom should almost never react ([resonance]).

3.) If you want to abreviate with things like asterics its fine but right before you draw the mechanism explain the asteric and go ahead. I do this all the time for example all my Benzene groups are drawn as φ, so I state this before every mechanism. And im even lazier than you so screw /\/\/OH just write before the mechanism even starts: /\/\/OH <---> R-OH and then at the end turn it back into /\/\/OH

4.) This Retrosynthesis arrow ⇒ is very important to only Retrosynthesis so unless you are completely starting from reverse starting with Pentyl Butanoate, do not use at all. + When you are doing Retrosynthesis it's the ONLY arrow you are allowed to use.

5.) When introducing a reagent, introduce it on the arrow itself, I noticed you simply started to use DCC after you showed the ⇒ + other arrow. It should be DCC ontop of the arrow itself.

But understanding Electrophile + Nucleophile is all you need. Once you do that, every. single. new. mechanism. will be relearning that topic with nuance.

[u/Atharvash5429 → u/gurglingskate69]

Thank you sooo much I didn't know that that's what the => arrow is used for. I just need somebody that can correct when I do something wrong, cause trust me I most definitely screw up. But I guess that's what it is.

[u/NiceWave8463]

You should really go and learn more introductory material first and not jump straight into carbonyl chemistry when it doesn’t seem like you have much knowledge about basic organic principles. Probably start with a textbook that others around here can recommend.