$CH\equiv C-CH_2-CH_3+Br_2\to CHBr=CBr-CH_2-CH_3$
$CH\equiv C-CH_2-CH_3+2Br_2\to CHBr_2-CBr_2-CH_2-CH_3$
$CH\equiv C-CH_2-CH_3+H_2\buildrel{{Pd/PbCO_3, t^o}}\over\longrightarrow CH_2=CHCH_2-CH_3$
$CH\equiv C-CH_2-CH_3+2H_2\buildrel{{Ni, t^o}}\over\longrightarrow CH_3-CH_2-CH_2-CH_3$
$CH\equiv C-CH_2-CH_3+H_2O\buildrel{{Hg^{2+}, t^o}}\over\longrightarrow CH_3-CH_2-CO-CH_3$
$CH\equiv C-CH_2-CH_3+H_2O\buildrel{{Hg^{2+}, t^o}}\over\longrightarrow CH_3-CH_2-CH_2-CHO$
