▁alco h ols ▁under go ▁fa cile ▁reduction ▁with ▁bor on ▁trif lu or ide ▁ ether ate ▁but ▁primary ▁alco h ols ▁require ▁an ▁excess ▁of ▁the ▁sil ane , ▁a ▁stronger ▁Lewis ▁acid , ▁and ▁longer ▁reaction ▁times . ▁ ▁Al ly lic ▁alco h ols ▁may ▁be ▁de ox y gen ated ▁in ▁the ▁presence ▁of ▁t ert i ary ▁alco h ols ▁when ▁eth ere al ▁l ith ium ▁per ch lor ate ▁is ▁employed . ▁ ▁Red u ctions ▁of ▁alk yl ▁hal ides ▁and ▁trif l ates ▁give ▁poor er ▁yields ▁in ▁general ▁than ▁redu ctions ▁of ▁alco h ols . ▁A ▁Lewis ▁acid , ▁typically ▁al umin ium ( III ) ▁ch lor ide ▁or ▁b rom ide , ▁is ▁required ▁regardless ▁of ▁the ▁substitution ▁pattern ▁of ▁the ▁alk yl ▁hal ide . ▁Ben zy l ▁hal ides ▁may ▁be ▁reduced ▁with ▁trif lu oro ac etic ▁acid ▁( T FA ) ▁in ▁high ▁yield . ▁ ▁H yd ros il anes ▁are ▁particularly ▁useful ▁for ▁the ▁reduction ▁of ▁ 1 , 1 - dis ub st it uted ▁double ▁b onds , ▁which ▁form ▁stable ▁t ert i ary ▁car b oc ations ▁upon ▁pro ton ation . ▁Tr is ub st it uted ▁double ▁b onds ▁may ▁be ▁reduced ▁select ively ▁in ▁the ▁presence ▁of ▁ 1 , 2 - dis ub st it uted ▁or ▁mon os ub st it uted ▁al ken es . ▁ ▁Not ably , ▁a rom atic ▁comp