Ester Hydrolysis Reaction Mechanism - Acid Catalyzed & Base Promoted Organic Chemistry

[@TheOrganicChemistryTutor]

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Thank you so much! It’s so calming watching these. Idk something about it makes me relax.

[@allywalton6074]

....youre watching these for fun? lol

[@nikkiralaniakea9527]

@@allywalton6074 no. For my organic chemistry and watching them while doing my homework made the anxiety subside a little because the way he teaches and explains things has a soothing effect.

[@unseenoo5192]

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[@koebiemi2095]

Just in case anyone had the same confusion as I did I sort of figured out why OCH3 is a bad Leaving Group (LG) during acid-catalyzed hydrolysis, but only when compared to its base-promoted counterpart. In basic conditions, the carbonyl Oxygen is not protonated initially, because the OH- molecules in the solution act as nucleophiles and attack the partially positive Carbonyl/middle carbon. In acidic conditions, the first step is the protonation of the carbonyl oxygen. Therefore, the resulting [tetrahedral intermediates] for each reaction are totally different. As for the tetrahedral intermediates::: In basic conditions, the former carbonyl carbon has a negative charge (3 lone pairs + one bond to the carbon) which can recreate the double bond with carbon and then the molecule can kick off the OCH3 group. VERSUS... in acidic conditions the former carbonyl carbon is now an O-H group (after being protonated) and has a neutral charge (two lone pairs + 2 bonds, like it prefers), so there isn't a reason (?) for the Oxygen to donate an electron pair to the central carbon, and therefore the OCH3 wouldn't get "kicked off" naturally without further steps. Hope this helps

[@samyakkumar1135]

8:05 if methanol is more acidic thwn water shouldn't its conjugate base be weaker than that of water?

[@pawlik455]

that is true, i had to double check the video if i heard it right. if something is a stronger acid then the conjugate base gonna be weaker and vice versa, if something is a stronger base then conjugate acid gonna be weaker, in short the methoxide is a very slightly weaker base than hydroxide

[@chatalola96]

Could you do a video on the Mechanism for Hydrolysis of an Ester with a tertiary alkyl group? Thanks your videos are great!

[@proy8613]

great videos. really helpful for my jee preparations

[@arkadas8196]

Yes, certainly!

[@bioboi4438]

1:25 - does the bond between the hydrogen and chlorine break due to the greater attraction of the H2O for another hydrogen being stronger than the covalent bond between the hydrogen and chlorine atom, or am I misunderstanding the mechanism?

[@rk-xz4gd]

Bro HCl is strong acid..so when dissolved in H2O it readily gives H+ and CL- ions. That's what a strong acid means...and then H+ attacks lone pair of oxygen in H2O and water is now protonated, we get H3O+

[@AndyLee-p9j]

08:13 There is a mistake here! methanol is slightly more acidic than water, so the basicity(base strength) of the methoxide should be weaker than the hydroxide.

[@AtulSapien]

no

[@Aliensariana]

im passing organic chemistry because of you

[@nurayaugarko9417]

How far this help you

[@anjalimourya6657]

😂

[@saamjamali8159]

I don’t know how to say thanks

[@NabihaAli-z2l]

You know 😜

[@Harsh-sm1sp]

Too Mt keh m keh dunga Teri jagah 😂

[@ibaiahunmuthoh3831]

Well explained sir. Thanks for the mechanism! It helps me a lot.

[@wendyfriz]

Where did the double bond in 4:19 go? And why is the white oxygen positive all the sudden???

[@M2JoyBoy]

Hi loved the video but at the beginning when you circled the Oxygen with the methyl group and said this “group was gonna leave” but when we went through the mechanism and saw it was only the methyl that leaves that confused me a bit 😅

[@alexandra95789]

Can you number the steps please. I like when the mechanisms look neat.

[@shujaatali7265]

Very nice explainatoon

[@Xandyy-vx4bw]

Why ch3o- is stable in basuc medium?

[@wkeyenjoyer]

Would the Naoh not just form sodium methanoate when hydrolysing the methyl methanoate?

[@exploreinsubria]

Does PET hydrolyse in 10% HCl ? Thanks.

[@anantharaam1390]

Sir,why in acidic medium methoxide ion is bad leaving group?? Pls reply...&thanks

[@danpuljic]

I believe its because the acid will react with the OCH3 molecule instead of catalysing the reaction, thus making it a better “leaving group” in a base catalysis reaction

[@DRBGW02]

Does anyone understand where the H2O on 5:28 came from???

[@brittneybunbury3989]

base hydrolysis 7:17

[@Sarah-hc6kj]

Thank you

[@TheOrganicChemistryTutor]

You're welcome

[@danielblumowski34]

Do esters that can by hydrolised only with acid exist?

[@user-ye6kv8lu4k]

what would determine the rate of reaction for base-catalyzed hydrolysis of an ester if you had 3 different esters?

[@newtoninspired]

very comprehensible! Thanks!

[@thegreateromentum]

Thank you for the video as always, super helpful! But I'm struggling to understand why the methoxide ion can't exist in acidic conditions? My thought process is that in acidic environments there is a surplus of H+ ions to stabilise the methoxide anion and so it should be more stable? Can someone help me here

[@smartstudywithaj6259]

Acids dissociate in water or aqueous solutions to form ions. These are responsible for the conduction of electricity. Acids don't dissociate hydrogen ions in absence of water. Therefore, we can say that acids produce ions only in aqueous solutions.

[@S1d2harth15]

Also in base catalysed why is och3 made to leave despite bad leaving group also it isnt protonated so still bad leaving group ..pls give me an answer as quickly as possible ..thanks

[@ankursingh1912]

Thank u sir you helped me for 3 years straight now I am getting AAs ... Sir during protonation the reason for oxgen in red getting protonated may due to its more basic nature i.e. immobile lonepairs. Thnks

[@PaulO-uj7xb]

Good day, Please can you describe what happens when a mixture of trialkylmonochlorosilane and dialkyldichlorosilane are hydrolysed. What are the products formed?

[@avivekninan11]

is this the same thing as de-esterification?

[@bhanusethia9556]

Thanks for mechanism sir👏👏

[@jesusmrosario-claudio4104]

Thank you once again.

[@mabe1272]

You're just great❤️

[@Lizbeth00777]

Is it can be happened in neutral condition?

[@mabe1272]

It's too slow solvent should act as a base or acid and that's not something to consider

[@vedantjadhav7805]

I had a doubt in this, not anymore

[@sarcaastech]

sir please make video of p block ,metallurgy,surface chemistry , solid state, solutions , polymers,biomolecules

[@TheOrganicChemistryTutor]

Unfortunately, I won't be ready any time soon to teach those subjects yet.

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The Organic Chemistry Tutor wil they be completed in coming 2-3 months ?

[@TheOrganicChemistryTutor]

The only video I plan on making in that list in the next few months is polymers. I'm going to stay away from the other topics for now.

[@alienware2149]

@The Organic Chemistry Tutor can u please say why och3- cannot exist in a acidic medium?..the video was wonderful though!!! ..

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thank you so much!

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Thanks!

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please use a better software, sometimes things aren't clear

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Bless 🙏🤗 you

[@Pseudonym77]

Can you do a video on orbital mechanics?

[@TheOrganicChemistryTutor]

I don't know that field too well to teach it at this point. I'm going to stay with the common subjects taught in high school and college for now.

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The Organic Chemistry Tutor​ ok I didn't know, but you videos are amazing.

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top tier

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Thanks

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Thank u!!

[@aleesya7467]

Thx

[@rilakkula]

i have feelings for you

[@nikodg194]

Esters do not hydrolysie in acidic solution as far as i know

[@ntcn0ah06]

Yes they do.

[@manmathgodre5360]

In strong conc acid in water solvant it can easily hydrolyzed