Destroyer #54 Orgo

[dentrilla]

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Hmm, says this is a acetoacetic ester synthesis. I'm wondering how the carbanion (created by removal of the super alpha hydrogen by a base) is able to attack CH3CH2Br, that is one EXTREMELY bulky nuc!!!

 

[Orgolover]

When attacking a primary alkyl halide it won't be a problem. You may have an argument for secondary alkyl halide though. However, here only substiution rxn will take place. Further, the alkoxide (carbanion) isn't EXTREMELY bulky as far as bulky goes---compare with KO-t-butyl which is HUGE.

 

[dentrilla]

Hmm, i see your point but have you looked at the question? it's just as bulky if not even bigger than t-butylO. It has the same number of C's and 2 extra O's..

But i guess its just really easy to attack a primary halide..