Question

S-2-iodooctane lost his opticaly activity in soln on tratment wwithNaI. Explain

Answer 1

Answer:

Repeated SN2 reactions occur leading to the formation of a racemic mixture

Explanation:

S-2-iodooctane is a chiral alkyl halide with an asymmetric carbon atom. The presence of an asymmetric carbon atom implies that it can rotate plane polarized light and thus lead to optical isomerism. The two configurations of the compound are R/S according to the Cahn-Prelong-Ingold system.

However, when S-2-iodooctane is treated with sodium iodide in acetone, repeated SN2 reactions occur since the iodide ion is both a good nucleophile and a good leaving group. Hence a racemic modification is formed in the system with time hence we end up with (±)- Iodooctane.