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(A) The reaction sequence is an example of acetoacetic ester synthesis.$1$. Acetoacetic ester $(CH_3COCH_2COOC_2H_5)$ reacts with $NaOEt$ to form an e

Vedclass · Accepted Answer

$CH_3-C(=O)-C(CH_3)(CH_2CH_2CH_3)-COOC_2H_5$

Vedclass · Answer

(A) The reaction sequence is an example of acetoacetic ester synthesis.$1$. Acetoacetic ester $(CH_3COCH_2COOC_2H_5)$ reacts with $NaOEt$ to form an enolate ion at the $\alpha$-carbon.$2$. This enolate reacts with $CH_3I$ via an $S_N2$ mechanism to produce ethyl $2$-methylacetoacetate $(CH_3COCH(CH_3)COOC_2H_5)$.$3$. Treatment with another equivalent of $NaOEt$ generates a new enolate at the same $\alpha$-carbon.$4$. This enolate reacts with $CH_3CH_2CH_2Br$ ($n$-propyl bromide) via $S_N2$ to yield the final product,ethyl $2$-methyl-$2$-propylacetoacetate,which is $CH_3-C(=O)-C(CH_3)(CH_2CH_2CH_3)-COOC_2H_5$.

Select the final product from this sequence of reactions.
Acetoacetic ester $\xrightarrow{NaOEt}$ $\xrightarrow{CH_3I}$ $\xrightarrow{NaOEt}$ $\xrightarrow{CH_3CH_2CH_2Br}$

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Acetic acid $\xrightarrow[\Delta]{\text{Thionyl chloride}} A$ $\xrightarrow{\text{Ammonia}} B$

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Select the final product from this sequence of reactions.Acetoacetic ester $\xrightarrow{NaOEt}$ $\xrightarrow{CH_3I}$ $\xrightarrow{NaOEt}$ $\xrightarrow{CH_3CH_2CH_2Br}$