Which of the following alkyl halides will undergo SN1 reaction most readily?

1.  ( CH3)3 C-F

2. ( CH3)3C-Cl 

3. (CH3)3C-Br

4. (CH3)3C-I

All the given compounds are tertiary alkyl halides but the bond formed between

carbon and iodine (C —|) bond is the weakest bond due to large difference in the size

of cartvon and iodine. So, (CH,),C—I gives SN1 reaction most ready. In other words,

iodine is a better leaving group.