Q-21-21-12P - Organic Chemistry (Mcmurry)

Question

Question: How could you prepare the following amides using an acid chloride and an amine or ammonia?

 

1.  ${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CH}}_{\mathbf{2}}{\mathbf{CONHCH}}_{\mathbf{3}}$

 

1. N,N-Dimethylbenzamide

 

1. Propanamide

 

Step-by-Step Solution

Answer

(a)

$$\begin{gathered} {\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{COCl}+2{\mathrm{CH}}_3{\mathrm{NH}}_2 \to {\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CONHCH}}_3 \\ \mathrm{N}-\mathrm{Methylpropanamide} \end{gathered}$$

(b) 

(c)

$$\begin{gathered} {\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{COCl}+{\mathrm{NH}}_3 \to {\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CONH}}_2 \\ \mathrm{Propanamide} \end{gathered}$$

Nuclephilic acyl substitution

The given reactions are examples of nuclephilic acyl substitution reaction.

The leaving grops in teh acyl chlorides is chloride ion. They will be substituted by the nucleophiles.

Subpart (a)

The required chemical reaction n is given as:

$$\begin{gathered} C{H}_{3}C{H}_{2}COCl+2C{H}_{3}N{H}_2 \to C{H}_{3}C{H}_{2}CONHC{H}_3\backslash \mathrm{hfill} \\ N-Methylpropanamide \end{gathered}$$

 

Subpart (b)

The chemical equation for the given reaction is as hown below:

Subpart (c)

The nucleophilic acyl substitution for the formation of  the given product is as shown below:

$$\begin{gathered} {\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{COCl}+{\mathrm{NH}}_3 \to {\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CONH}}_2 \\ \mathrm{Propanamide} \end{gathered}$$