Identify all the possible monochloro structural isomers expected to be formed on free radical monochlorination of (CH3)3CHCH2CH3
There would be three possible products on the basis of stability of the carbon radical and the relative reactivity of the 1°: 2°: 3° hydrogen atoms of the 1°: 2°: 3° carbon radical obtained. Since, for electron withdrawing species (Cl-atom) -I effect is applied and so stability of the carbon radical is in order of 3°> 2°> 1° so reactivity of free radicals will be of 3°> 2°> 1° in (CH3)2CHCH2CH3 ( the given formula is wrong as carbon should have only four valency) in free radical monochlorination.
So, the product obtained is :
ClC(CH3)2CH2CH3 (45.9%) , (CH3)2CH-CHClCH3 (38.8%) ,(CH3)2CHCH2CH2Cl ( 15.3%).