Malonic Ester synthesis - Chad

[jpark1800]

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Chad says that because (in malonic ester synthesis), the H between the two carbonyls is very acidic, we use NaOH to deprotonate, not LDA. Why don't you use LDA. I thought that to deprotonate an acidic hydrogen you need a very strong base. Do you need a strong base to deprotonate an acidic hydrogen?

 

[Menthol]

to deprotonate an acidic hydrogen
you dont need a strong base

 

[NhuPT]

NaOH is a strong base, LDA is a large hindered base

 

[Dotoday]

LDA is tood big and therefore too hindered to abstract a double alpha proton.