Question

Question: Draw the products formed in the crossed aldol reaction of phenylacetaldehyde $\left(C_6{H}_{5}C{H}_{2}CHO\right)$with each compound: (a) $\mathit{C}{\mathit{H}}_{\mathbf{2}}{\left(COOEt\right)}_{\mathbf{2}}$; (b) $\mathit{C}{\mathit{H}}_{\mathbf{2}}{\left(COC{H}_3\right)}_{\mathbf{2}}$; (c) $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{C}\mathit{O}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}\mathit{N}$.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Crossed aldol reaction

Aldol reaction carried out using two different (non-identical) carbonyl compounds is referred to as the crossed aldol reaction.

Crossed aldol reaction mechanism

A crossed-aldol reaction is shown below.

Crossed aldol reaction

Products formed in a crossed aldol reaction

a. The reaction of $C_6{H}_{5}C{H}_{2}CHO$with $C{H}_2{\left(COOEt\right)}_2$ is represented below:

Reaction of phenyl acetaldehyde with $C{H}_2{\left(COOEt\right)}_2$

b. The reaction of $C_6{H}_{5}C{H}_{2}CHO$ with $C{H}_2{\left(COC{H}_3\right)}_2$is represented below:

Reaction of phenyl acetaldehyde with $C{H}_2{\left(COC{H}_3\right)}_2$

c. The reaction of $C_6{H}_{5}C{H}_{2}CHO$ with $C{H}_{3}COC{H}_{2}CN$ is represented below:

Reaction of phenyl acetaldehyde with$C{H}_{3}COC{H}_{2}CN$