Q29E - Organic Chemistry (Mcmurry)

Question

The following structure represents a tetrahedral alkoxide-ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product (green = Cl).

Step-by-Step Solution

Answer

Intermediate can be prepared acid chloride and nucleophile

 

The final product amide can be prepared as from the intermediate as 

 

Step 1: The Nucleophile and the Starting Acid Derivative

Acid chloride reacts with NH₃ nucleophile to give the intermediate:

Step 2: Leaving Group and Final Product

Intermediate leaves the Cl^- ion and produces the amide.