$Cl_2/ AlCl_3 \Rightarrow$ Electrophilc aromatic substitution.
According to Baker-Nathan effect, hyperconjugation dominates over inductive effect. Hence ortho-position of methyl group has more $e^-$ density for $EAS$
$CH_3CH_2CH_2Br + NaCN \to $$CH_3CH_2CH_2CN+ NaBr$
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