i.Both the alkyl groups attached to the oxygen atom are primary, therefore attack of Br – ion occurs on the smaller methyl group leading to the formation of Propan-1-ol and Bromomethane.
ii. Due to resonance, C6H5-O bond has some double bond character and hence, is stronger than O →C2H5 bond. Therefore, the cleavage of the weaker O→C2H5 bond occurs to yield Phenol and Bromoethane.
iii. Due to the strong +R effect of the O →C2H5 group, it is activating as well as o, p-directing . Therefore nitration of ethoxybenzene will give a mixture of 2-Ethoxynitrobenzene. and 4-Ethoxynitrobenzene.
iv. Since tert-Butyl carbocation is much more stable than ethyl carbocation, reaction follows SN1 mechanism leading to the formation of tert-butyl iodide and ethanol as shown below: HI→ H+ + I-
Step I: Formation of carbocation:
