MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN2 mechanism, rate, stereochemistry, steric effects
JEE Advanced levelNumerical answerDifficulty 3 of 3o3096

Optically pure -2-iodooctane is stirred in acetone with a very large excess of radioactive , so the labelled iodide concentration stays essentially constant. Every substitution is a clean SN2 reaction with complete inversion, and the rate constant for substitution is the same for every molecule, whether or not it already carries a label. At a certain time of the substrate molecules are still unlabelled. What is the optical purity (enantiomeric excess) of the substrate then, in percent? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 49

For a given molecule, unlabelled iodine survives only if no substitution has occurred, so the fraction unlabelled is . Each substitution inverts the configuration, and the enantiomeric excess is the average of over the Poisson-distributed number of substitutions, giving . Therefore , i.e. . (Racemisation is twice as fast as exchange.)
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN2 mechanism, rate, stereochemistry, steric effects

More questions on SN2 mechanism, rate, stereochemistry, steric effects