Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?………….

Question 24:Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?The following questions are case-based questions. Each question has an internal
choice and carries 4 (1+1+2) marks each. Read the passage carefully and answer the
questions that follow.

The correct answer is – Allyl chloride is hydrolyzed more readily than n-propyl chloride due to the presence of the allyl group. The allyl group is a three-carbon chain with a double bond between the first and second carbon atoms and a single bond between the second and third carbon atoms. This double bond makes the allyl group more electron-withdrawing and less basic compared to a simple alkyl group, such as the propyl group. This means that the electron density on the carbon atom bonded to the chlorine atom in allyl chloride is lower than in n-propyl chloride. In the presence of water, the chloride ion in allyl chloride is a better leaving group due to the electron-deficient nature of the allyl group. This makes it easier for water molecules to attack the carbon atom and displace the chloride ion, resulting in the formation of allyl alcohol. In contrast, the electron density on the carbon atom in n-propyl chloride is higher, making it less susceptible to attack by water molecules. As a result, n-propyl chloride hydrolyzes more slowly than allyl chloride. Overall, the presence of the electron-withdrawing allyl group in allyl chloride makes it more reactive towards hydrolysis compared to n-propyl chloride.