Do the following conversions :
(i) Toluene to benzyl alcohol
(ii) Ethanol to but - 2 - yne
(iii) Ethanol to propane nitrile
(iv) Propane to propan-1-ol
(v) Ethyl chloride to propanoic acid.

Explanation

(i)
(ii) `underset("Ethanol")(C_(2)H_(5)-OH) overset(P//I_(2), triangle)to C_(2)H_(5)I underset(Delta)overset(KOH(alc))to CH_(2)=CH_(2) overset(Br_(2), CCl_4)to underset(Br)underset(|)(CH_(2))-underset(Br)underset(CH_(2))`
(iii) `underset("Ethanol")(C_(2)H_(5)-OH) overset(P//I_(2), triangle)to C_(2)H_(5)-I underset(H_(2)O)overset(KCN, OH^(-))to underset("Propane nitrile")(C_(2)H_(5)-CN)`
(iv) `underset("Propane")(CH_(3)CH=CH_(2)) overset("HBr/Perioxide")to CH_(3)CH_(2) CH_(2) Br overset("Aq KOH")to underset("Propan-1-ol")(CH_(3)CH_(2)CH_(2)OH)`
(v) `underset("Ethyl chloride") (C_(2)H_(5)-Cl) overset(KCN, E_(1)OH, H_(2)O)to C_(2)H_(5)-CN overset(H^(+), H_(2)O)to underset("Propanoic acid") (CH_(3)CH_(2)OOH)`