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

Identify $C$ in the following sequence of reactions:
$2\text{-methylcyclohexanecarboxylic acid}$ $\xrightarrow{SOCl_2} A$ $\xrightarrow{NH_3} B$ $\xrightarrow{P_4O_{10}, \text{heat}} C(C_8H_{13}N)$

What are $X$ and $Y$ respectively in the following reaction sequence?
$C_6H_5CH_3$ $\xrightarrow{X} C_6H_5CO_2H$ $\xrightarrow{Y} C_6H_5CH_2OH$

Which one of the following compounds forms a red coloured solution on treatment with neutral $FeCl_3$ solution?

Which acid is the strongest?

Identify the major product $Y$ from the following reaction:

Vedclass Test Series

Exam Paper Generator

Online Exam Module