When ethyl acetoacetate reacts with one mole | vedclass

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Question

(C) Ethyl acetoacetate $(CH_3-CO-CH_2-CO_2Et)$ contains an active methylene group $(-CH_2-)$ situated between two electron-withdrawing carbonyl groups

Vedclass · Accepted Answer

$CH_3-CO-CH(MgI)-CO_2Et$

Vedclass · Answer

(C) Ethyl acetoacetate $(CH_3-CO-CH_2-CO_2Et)$ contains an active methylene group $(-CH_2-)$ situated between two electron-withdrawing carbonyl groups. The protons on this carbon are relatively acidic $(pK_a \approx 11)$. Grignard reagents like methyl magnesium iodide $(CH_3MgI)$ act as very strong bases. In the presence of acidic protons,the acid-base reaction (deprotonation) occurs much faster than nucleophilic addition to the carbonyl group. Therefore,one mole of $CH_3MgI$ will abstract a proton from the active methylene group to form a magnesium enolate salt and methane gas. $CH_3-CO-CH_2-CO_2Et + CH_3MgI \rightarrow CH_3-CO-CH(MgI)-CO_2Et + CH_4 \uparrow$

When ethyl acetoacetate reacts with one mole of methyl magnesium iodide,the product of the reaction will be:

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