OC Question -- Please help :)

[NguyenDDS]

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Hello everyone! 🙂

I am wondering why the nucleophile attacks the H on the OH, instead of attacking the C of the carbonyl? Isn't the C of the C=O partially positive, making is a good place to attack? I must be missing a very important concept....

Thanks!!

 

[casper22]

Hello everyone! 🙂

I am wondering why the nucleophile attacks the H on the OH, instead of attacking the C of the carbonyl? Isn't the C of the C=O partially positive, making is a good place to attack? I must be missing a very important concept....

Thanks!!

The Grignard Reagent here is highly reactive as the Ph part of the reagent will have a negative charge..thus the reagent acts as both nucleophile and base, and when it reacts with a compound that has a proton attached to a more electronegative compound as in this case, H connected to O, the Grignard reagent acts a base and completes the reaction as show thus destroying the reagent

so technically, you cannot use a Grignard Reagent when the compound has a proton attached to a high electronegative compound...similarly you cannot have a Grignard reagent with a OH group on it..

I hope this helps.