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Which reagent distinguish propyne and propene?

1. Alkaline ${\mathrm{KMnO}}_{4}$

2. ${\mathrm{Cu}}_{2}{\mathrm{Cl}}_{2}$ + ${\mathrm{NH}}_{4}\mathrm{Cl}$

3. ${\mathrm{Br}}_{2}$ water

4. ${\mathrm{Cu}}_{2}{\mathrm{Cl}}_{2}$ + ${\mathrm{NH}}_{4}\mathrm{OH}$