The product which is not expected to be forme | vedclass

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Question

(A) The reaction is a cross-aldol condensation between benzaldehyde $(C_6H_5CHO)$ and propanal $(CH_3CH_2CHO)$.Benzaldehyde has no $\alpha$-hydrogen,s

Vedclass · Accepted Answer

$C_6H_5CH=CH-CH_2-CHO$

Vedclass · Answer

(A) The reaction is a cross-aldol condensation between benzaldehyde $(C_6H_5CHO)$ and propanal $(CH_3CH_2CHO)$.Benzaldehyde has no $\alpha$-hydrogen,so it cannot form an enolate ion.Propanal has $\alpha$-hydrogens and can form an enolate ion $(CH_3-CH^--CHO)$.Possible products include:$1$. Self-aldol of propanal: $CH_3CH_2CH(OH)CH(CH_3)CHO$,which dehydrates to $CH_3CH_2CH=C(CH_3)CHO$.$2$. Cross-aldol (benzaldehyde as electrophile,propanal as nucleophile): $C_6H_5CH(OH)CH(CH_3)CHO$,which dehydrates to $C_6H_5CH=C(CH_3)CHO$.$3$. The product $C_6H_5CH=CH-CH_2-CHO$ would require the formation of an enolate from propanal at the terminal methyl group,which is not the kinetic or thermodynamic pathway for this reaction,or it would require benzaldehyde to act as a nucleophile,which is impossible.Thus,$C_6H_5CH=CH-CH_2-CHO$ is not expected to be formed.

The product which is not expected to be formed in the following reaction is:
$C_6H_5CHO + CH_3CH_2CHO \xrightarrow{OH^-(aq.), \Delta} \text{Product}$

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The product which is not expected to be formed in the following reaction is:$C_6H_5CHO + CH_3CH_2CHO \xrightarrow{OH^-(aq.), \Delta} \text{Product}$