When ethyl acetoacetate reacts with one mole | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

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:

Similar Questions

Ionic species are stabilized by the dispersal of charge. Which of the following carboxylate ions is the most stable?

Saponification of ethyl benzoate with caustic soda as alkali gives:

For the following three esters, the order of rates of alkaline hydrolysis is:
$(I)$ $p-NO_2-C_6H_4-COOCH_3$
$(II)$ $p-CH_3O-C_6H_4-COOCH_3$
$(III)$ $p-CH_3-C_6H_4-COOCH_3$

Which of the following compounds will $NOT$ produce acetamide upon reaction with ammonia?

The acid which reduces Fehling solution is

Vedclass Test Series

Exam Paper Generator

Online Exam Module