Organic synthesis: compare question

A student plans to prepare the compound methyl 3-oxobutanoate, $\ce{CH3COCH2CO2CH3}$, which contains both a ketone and an ester group. Two routes are proposed.

Route 1: $\ce{CH3COCH3}$ is treated with $\ce{Cl2}$ in the presence of $\ce{NaOH}$ to give $\ce{CH3COCH2Cl}$. This is then reacted with $\ce{KCN}$, followed by acidic hydrolysis and then esterification with methanol.

Route 2: $\ce{CH3CO2CH3}$ is treated with $\ce{CH3COCl}$ in the presence of $\ce{AlCl3}$.

Compare the two routes in terms of the type of reaction occurring in each step, the reagents and conditions needed, and any likely by-products. State, with a reason, whether each route can succeed.