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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

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

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

I don’t know how to say thanks

im passing organic chemistry because of you

great videos. really helpful for my jee preparations

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

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 😅

very comprehensible! Thanks!

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

Thank you

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

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

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

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

thank you so much!

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

Thank you once again.

base hydrolysis 7:17

You're just great❤️

Thanks for mechanism sir👏👏

Thanks!

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

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

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

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

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

Does PET hydrolyse in 10% HCl ? Thanks.

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?

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

Why ch3o- is stable in basuc medium?

Do esters that can by hydrolised only with acid exist?

I had a doubt in this, not anymore

top tier

Thanks

Bless 🙏🤗 you

Thank u!!

is this the same thing as de-esterification?

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

Is it can be happened in neutral condition?

Thx

Can you do a video on orbital mechanics?

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