Predict the products of the following reactions :
(i) `CH_(3)-CH_(2)-CH_(2)-O-CH_(3)+HBrrarr`
(ii)
(iii)
(iv) `(CH_(3))_(3)C-OC_(2)H_(5)+HIrarr`

Explanation

(i) The reaction involves the cleavage of C-O bond. The Br atoms of HBr is to combine with the smaller relkyl grouop to give the following prodcuts.
`CH_(3)-underset("1-Methoxypropane")(CH_(2)-OCH_(3))+HBr rarrCH_(3)-underset("Propan-1-ol")(CH_(2)-CH_(2)-OH)+underset("Methyl bromide")(CH_(3)Br)`
For more details and explanation, consult section 12.24.
(ii) This reaction also proceeds in the same manner. The Br atom of HBr is expected to combine with ethyl group (smaller in size) and not with phenyl group (bigger is size)

(iii) Nitrating mixture brings about the nitration of benzene ring. The ethoxy group `(OC_(2)H_(5))` is an activating group and increases the electron denisty at the ortho and para positions due to +M effect. of o-nitro and group at the para position than at the ortho position in the ring.

(iv) In this reaction, the ether is initially protonated by `H^(+)` ion of the acid HI. It is then expected to undergo cleavage to accomodate `I^(-)` ion (nucleophile) . The reaction follows `S_(N^(1))` mechanism.