In a classic experiment, Edward Hughes (a colleague of Ingold’s at University College, Lon...

In a classic experiment, Edward Hughes (a colleague of Ingold’s at University College, London) studied the rate of racemization of 2-iodooctane by sodium iodide in acetone and compared it with the rate of incorporation of radioactive iodine into 2-iodooctane.

How will the rate of racemization compare with the rate of incorporation of radioactivity if

(a) Each act of exchange proceeds stereospecifically with retention of configuration?

(b) Each act of exchange proceeds slereospecifically with inversion of conliguration?

(c) Each act of exchange proceeds in a stereorandom manner, in which retention and inversion of configuration are equally likely?