Ochem help

[asckwan]

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What is the product? C6H5CH2CO2CH3 reacted with NaOCH3

My question is how do you know when the nucleophile attacks the carbonyl Carbon or strips the acidic Hydrogen.

 

[DAT Destroyer]

see any text Dr Romano Orgoman.com

 

[grapeflavorsoda]

What is the product? C6H5CH2CO2CH3 reacted with NaOCH3

My question is how do you know when the nucleophile attacks the carbonyl Carbon or strips the acidic Hydrogen.

ester's alpha hydrogen is not as acidic as ketone's or aldehyde's.

thus alpha hydrogen's pKa will be greater than 16. and alkoxide group's pKa is around 15-16 range which is not basic enough to produce enough enolate contents in esters. so the immediate dominant reaction when you mix ester with alkoxide or hydroxide would be nucleophilic attack of anionic oxygen to carbonyl carbon.