Question

Rank the reactivity of each known alkyl halide (1-chlorobutane, 1-bromobutane, 2-bromobutane, benzyl chloride, 2-chloro-2-methyl propane, 2-bromo-2methyl propane) in a NaI/Acetone Test and in an AgNO₃/EtOH Test.

Answer 1

NaI /acetone is Sn2 condition

in SN2 reaction reactivity of alkyl halides as follows

primary > secondary > tertiry

halides as follows

iodides > bromides > chlorides

benzyl chloride > 1-bromo butane > 1 -chloro butane > 2-bromobutane > 2-bromo-2methyl propane >  2-chloro-2-methyl propan

AgNO3 /ETOH also SN2 mechanism so follows same order

benzyl chloride > 1-bromo butane > 1 -chloro butane > 2-bromobutane > 2-bromo-2methyl propane >  2-chloro-2-methyl propan