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Question 57 of 66

Q.How will you convert Ethylacetate into Ethylaceto acetate ?

Puducherry TnboardTamil Nadu HSC (DGE) Board 2023Subjective· 3mImportance★★★★★
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Two molecules of ethyl acetate undergo Claisen condensation, catalysed by sodium ethoxide: the enolate of one molecule attacks the ester carbonyl of the other, kicking out ethoxide to give ethyl acetoacetate.

Ethyl acetate, CH3COOC2H5CH_3COOC_2H_5, has alpha-hydrogens on the CH3CH_3 group adjacent to the carbonyl, which are acidic enough to be removed by a strong base like sodium ethoxide (NaOC2H5NaOC_2H_5), generating an ester enolate: CH3COOC2H5+NaOC2H5→−CH2COOC2H5 (enolate)+C2H5OHCH_3COOC_2H_5 + NaOC_2H_5 \rightarrow {}^-CH_2COOC_2H_5\ (\text{enolate}) + C_2H_5OH This carbanion/enolate then performs a nucleophilic acyl substitution, attacking the carbonyl carbon of a second molecule of ethyl acetate and displacing ethoxide ion: CH3COOC2H5+−CH2COOC2H5→CH3−CO−CH2−COOC2H5+−OC2H5CH_3COOC_2H_5 + {}^-CH_2COOC_2H_5 \rightarrow CH_3-CO-CH_2-COOC_2H_5 + {}^-OC_2H_5 After acidic workup, the product is ethyl acetoacet …

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