Q11-76E - Organic Chemistry (Mcmurry)

Question

The reaction of 1-chlorooctane with CH₃CO₂ 2 to give octyl acetate is greatly accelerated by adding a small quantity of iodide ion. Explain

Step-by-Step Solution

Answer

Formation of the desired product

Step 1: Substitution reaction

Nucleophilic substitution reactions are one of the most common and versatile reaction types in organic chemistry because in this each step involves the substitution of one nucleophile with another nucleophile.

Step 2: Explanation

The reaction will be accelerated by adding an iodide ion because the iodide ion is a good nucleophile when compared to the acetate ion. So, it will react first and the formed iodo compound can be attacked by the acetate ion because the iodide ion is a good leaving group.

The reaction is represented as:

Formation of the desired product