Q19-10P - Organic Chemistry (Mcmurry)

Question

Show the products you would obtain by acid-catalyzed reaction of cyclohexanonewith ethylamine, CH₃CH₂NH₂, and with diethylamine, (CH₃CH₂)₂NH.

Step-by-Step Solution

Answer

Step 1:Nucleophile addition of Amine

The addition of Primary aminesto aldehydes and ketones forms imines having the chemical formula ${\mathbf{R}}_2\mathbf{C}\mathbf{=}\mathbf{NR}$ ,which is an intermediate in biological pathways, where they are often called Schiff bases.

 The addition of Secondary amines to aldehyde and ketone forms enamine, having the chemical formula ${\mathbf{R}}_2\mathbf{N}\mathbf{-}\mathbf{CR}\mathbf{=}{\mathbf{CR}}_2$.

Step 2: Acidic catalyzed addition of Amine

The acid-catalyzed reaction of cyclohexanone (ketone) with ethylamine $\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}\right)$, a primary Amine, results in imine formation.  

The formation of imine results by replacing carbonyl functional group C=O to functional group having C=NR.

The acid-catalyzed reaction of cyclohexanone (ketone) with diethylamine ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_2\text{NH}$, a secondaryamine, results in enamine formation.

The formation of enamine results by replacing the carbonyl functional group C=O to the functional group having ${\text{C-NR}}_{\text{2}}$ .

Formation of imine and enamine