S YNTHESIS
OF
TERT-BUTYL
CHLORIDE
THROUGH
HYDROCHLORINATION OF TERT-BUTYL ALCOHOL AND PURIFICATION USING DISTILLATION J. V. DE GUZMAN DEPARTMENT OF CHEMICAL OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING OF ENGINEERING UNIVERSITY OF UNIVERSITY OF THE THE PHILIPPINES, DILIMAN QUEZON CITY , PHILIPPINES DATE PERFORMED: FEBRUARY 27, 2015 INSTRUCTOR’S NAME : ALLAN KENNETH REGUNTON
ABSTRACT Preparation o a!"#! $a!i%e& $o!%& &i'ni()an)e &i'ni()an)e not on!# in t$e &t*%# o t$e+ *t a!&o in it& pra)ti)a! app!i)ation& in t$e (e!%& o +e%i)ine, a'ri)*!t*re an% in%*&tr#- T$e p*rpo&e o t$i& e.peri+ent i& to &#nt$e&i/e t0*t#! )$!ori%e t$ro*'$ a n*)!eop$i!i) n*)!eop$i!i) &*&tit*tion rea)tion o t0*t#! a!)o$o! 1it$ HC!- T$i& +et$o% e+p!o#& t$e re!ati2e &tai!it# o t$e )aro)ation inter+e%iate or+e% an% t$*& pro)ee%& t$ro*'$ S N3 rea)tion +e)$ani&+- T$e )r*%e pro%*)t otaine% 1a& t$en p*ri(e% *&in' ra)tiona! %i&ti!!ation t$at +a"e& *&e o t$e %i4eren)e in t$e oi!in' point& o i+p*ritie& an% %e&ire %e&ire% % &*&ta &*&tan)e n)e-- T$e per)en per)enta' ta'e e #ie!% #ie!% i& 56-789 56-789 i+p!#i i+p!#in' n' t$e e4e)ti e4e)ti2it 2it# # o $#%ro$a!o'enation o tertiar# a!)o$o!& to pro%*)e tertiar# a!"#! $a!i%e& an% t$e *&e o %i&ti!!ation a& a p*ri()ation te)$ni:*e or !i:*i%&- It a!&o &$o1& e4e)ti2e re+o2a! o 1ater in t$e )r*%e pro%*)t t$at )an )on2ert t0*t#! )$!ori%e a)" to a!)o$o! an% +ini+i/e% error& &*)$ a& !oo&e %i&ti!!ation &et0*p an% )onta+ination o ;a&"& an% oi!in' )$ip& _____________________________________________________________________________________________ __________________________________________________________________________ ___________________ _________________________________
INTRODUCTION Al!l Al!l "#l$%&' "#l$%&' #l'( )#ll&% )#ll&% "#l(#l#* "#l(#l#*&' &' #+& )l#'' ( )(-.(/*%' $" # "#l(&* #(- 3(*%&% ( # '. 4"!3+$%$6&% )#+3 )#+3(* (* #(#(- 489 H#l( H#l(& &* * #(#(- $' -(+& -(+& &l&) &l&)+ +(* (*& &# #$; $;& & "#* "#* )#+3 )#+3(* (* #(- -#$* "& C 3(*% .(l#+ #*% #l #l!l "#l$ "#l$%& %&' ' -(l& -(l&)/ )/l& l& ( 3& -(+ -(+& .(l# .(l#++ "#* "#* "!%+ "!%+() ()#+ #+3( 3(*'9 *'9 H(& H(&;& ;&+, +, "&! "&! #+& #+& '$ll '$ll )(*'$% )(*'$%&+ &+&% &% $*'(l/ $*'(l/3l& 3l& $* #& #&++ 3&)# 3&)#/' /'& & $ )#**( )#**( (+(+- #* H 3(*% $" "& #&+ -(l&)/l&9 Al Al!l "#l$ "#l$%& %&' ' #+& #+& )#& )#&( (+$ +$6& 6&% % $*( $*( "+&& "+&&,, %&.& %&.&*% *%$* $* (* "& */-3 */-3&+ &+ ( #l #l!l '/3' '/3'$ $/ /&* &*' ' ## ##)" )"&% &% ( "& "& )#+3(* #(- +(- "$)" "& "#l(&* $' 3(*%&%9 P+$-#+! #l!l "#l$%&' "#;& #
"#l(&* #(- 3(*%&% ( # )#+3(* $" (*& #l!l '/3'$/&* "$l& # '&)(*% '&)(*%#+! #+! #l!l #l!l "#l$%& "#l$%& "#' # )#+3( )#+3(* * $" ( #l!l #l!l '/3'$/&* '/3'$/&* )(**&)&% ( "& "#l(&*9 "#l(&*9 T&+$#+! &+$#+! #l!l #l!l "#l$%&' "#l$%&' "#;& "& "#l(&* #(- 3(*%&% ( # )#+3(* #(- $" "+&& #l!l +(/.'9 H#l(#l#*&' (/*% -#*! $*%/'+$#l #*% ."#+-#)&/$)#l #..l$)#$(*', $*)l/%$* "&$ "&$++ /'& #' '(l; '(l;&* &*' ',, +&+ +&+$ $&+# &+#* *', ', .&'$)$%&', /*$)$%&' #*% #*&'"&$)'9 T"&! #+& #l'( $*%$'.&*'#3l& $* $;$* $-.(+ $-.(+#* #* l&#%' ( *& -&%$)$ -&%$)$*&' *&'99 18 A' '/)", -&"(%' $* '!*"&'$6$* #l!l "#l$%&' &+& %&;&l(.&% 3&)#/'& ( $' $-.( $-.(+# +#*) *)& & *( *( (*l! (*l! $* "& "& '/% '/%! ! ( 1
"&'& )(-.(/*%' 3/ #l'( $* "&$+ .+#)$)#l #..l$)#$(*' $* "& <&l%' ( -&%$)$*&, $*%/'+! #*% #+$)/l/+&9 Al!l "#l$%&' )#* 3& .+&.#+&% "+(/" +#%$)#l "#l(&*#$(* ( #l#*&', #ll!l$) "#l(&*#$(* ( #l&*&', +&#)$(* $" G+$*#+% +&#&*' 3/ "& -(' &*&+#ll! /'&/l -&"(% $' .+&.#+#$(* +(- #l)("(l'9 18 Al)("(l' +&#) $" "!%+("#l(&*#&% )(-.(/*%' '/)" #' HCl #*% HB+ ( !$&l% #l!l "#l$%&' $* # !.& ( +&#)$(* )#ll&% */)l&(."$l$) '/3'$/$(*9 T"$' -&"(% $' -(' #..l$)#3l& $* "& '!*"&'$' ( &+$#+! #l!l "#l$%&' +(&+$#+! #l)("(l' '$*)& .+$-#+! #*% '&)(*%#+! #l)("(l' +&#) -/)" 'l(l! $* "& .+&'&*)& ( HCl (+ HB+9 T"& &*&+#l +&#)$(* (+ '!*"&'$' ( &+$#+! #l!l "#l$%& $' '"(* $* "& </+& 3&l(:
'/3'$/$(* +&#)$(* ( #l)("(l' $" "!%+(&* "#l$%& #*% "& .(''$3l& '$%& +&#)$(*' "# -#! ())/+ %/+$* '!*"&'$'9 I #l'( $*&*%' ( &;#l/#& "& &@)$&*)! ( %$'$ll#$(* #' # ./+$<)#$(* &)"*$=/&9 METHODOLOGY I* "& %+! 50-l '&.#+#(+! /**&l, 10 -l ( 3/!l #l)("(l #*% 20 -l )(l% )(*)&*+#&% HCl &+& )(-3$*&% #*% #ll(&% ( +&#)9 T"& $*&+*#l .+&''/+& "# 3/$l /. $* "& '&.#+#(+! /**&l #' +&l$&;&% +(- $-& ( $-& 3! 'l(l! (.&*$* "& '(.)()9 T"& -$?/+& #' #ll(&% ( '#*% /*%$'/+3&% $* # '&/. #' '"(* $* F$/+& 2 (+ 20 -$*/&'9 T( (+)& '&.#+#$(* ( l#!&+', 45 -l ( M N#Cl '(l/$(* #' #%%&% $* "& -$?/+&9
H Figure 19 G&*&+#l +&#)$(* ( &+$#+! #l)("(l ( !$&l% #l!l "#l$%& D$'$ll#$(*, (* "& ("&+ "#*%, $' # .+()&'' ( ;#.(+$6$* # l$=/$%, )(*%&*'$* "& ;#.(+, #*% (3#$*$* "& )(*%&*'#& $* #*("&+ )(*#$*&+ 28 9 I )#* 3& /'&% #' # -&"(% ( ./+$!$* # '/3'#*)& 3! #$* #%;#*#& ( "& %$>&+&*)& $* "& 3($l$* .($*' ( "& $-./+$$&' "# -#! 3& .+&'&* #*% ( "& '/3'#*)& ( 3& ./+$<&%9 T"$' $' '.&)$<)#ll! )#ll&% #' +#)$(*#l %$'$ll#$(*9 T"& )(-.(/*% ( 3& ./+$<&% $' (3#$*&% 3! %$'$ll$* "& '(l/$(* #*% )(ll&)$* "& +#)$(*' # "& 3($l$* .($* ( "& '/3'#*)& ( $*&+&'9 T"$' &?.&+$-&* ()/'&' (* "& .+&.#+#$(* ( &+3/!l )"l(+$%& +("& +&#)$(* ( &+3/!l #l)("(l #*% "!%+()"l(+$) #)$%9 A&+ "& '!*"&'$', 3/!l )"l(+$%& $' ./+$<&% /'$* +#)$(*#l %$'$ll#$(*9 T"$' &?.&+$-&* #l'( #$-' ( &?.l(+& "& -&)"#*$'-' $*;(l;&% $* "& */)l&(."$l$)
58
Figure 9 S&/. (+ "& '&.#+#$(* ( #=/&(/' #*% (+#*$) l#!&+
T"& #=/&(/' l#!&+ #' %+#$*&%9 T( )"&) "# $ #' "& #=/&(/' l#!&+, 1 2 %+(.' ( #&+ #' #%%&% ( $ #*% .('$$;& +&'/l $' '"(* 3! %$''(l/$(* ( #&+ $* "$' l#!&+9 I-./+$$&' #*% &?)&'' +&#)#*' &+& +&-(;&% +("& .+(%/) 3! #%%$* '(l$% N#HCO 4 $* "& (3#$*&% (+#*$) l#!&+ $*'$%& # %+! #'9 T"& -$?/+& #' %&)#*&% #*% "& )(ll&)&% '(l/$(* #' /+"&+ %+$&% 3! #%%$* '-#ll #-(/* ( #*"!%+(/' C#Cl2 /*$l $ *( l(*&+ )l/-.&% (&"&+9 T"& +&'/l$* '(l/$(* #' %&)#*&% $*( # %+! 25-l +(/*% 3((- #' #*% & 3($l$* )"$.' &+& #%%&%9 2
A %$'$ll#$(* '&/. '$-$l#+ ( F$/+& 4 #' )(*'+/)&%9 T"& (3#$*&% '(l/$(* #' "&* %$'$ll&%9
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Figure !9 S$-.l& %$'$ll#$(* S&/.
"& *& .#+$#ll! *&#$;& N/C 3(*% "$)" $' .#+l! (+-$* "&+&3! -#$* "$' +&#)$(* '&+&('.&)$<)189 H(&;&+, "$' %(&' *( ())/+ # # "$*%&+&% '/3'+#& 3&)#/'& "& */)l&(."$l& )#**( &#'$l! ##) "& 3/l! #*% '&+$)#ll! "$*%&+&% )#+3(* #(- "&+&(+& $ $' l&#' (+ ;&+! 'l( ( ())/+ $* &+$#+! (+ '#3l& #l)("(l'9 O* "& ("&+ "#*%, SN1 +&#)$(* $' # /*$-(l&)/l#+ ('&. */)l&(."$l$) '/3'$/$(* "$)" $' *(* '&+&('.&)$<)9 T"& +#& l$-$$* '&. $* "$' +&#)$(* $' "& (+-#$(* ( # '#3$l$6&% )#+3()#$(* $*&+-&%$#&, "/', "& -(+& '#3l& "& )#+3()#$(* $' (+-&%, "& #'&+ "& +&#)$(* $'9 T"&+&(+& "& */)l&(."$l$) '/3'$/$(* ( #l)("(l' )#* 3& '/--#+$6&% $*(:
T"& +#)$(* "# 3($l&% # 25 C #' )(ll&)&% $* # .+&&$"&% ;$#l .l#)&% $* # )(l% #&+ 3#"9 T&+3/!l )"l(+$%& .&+)&*#& !$&l% #' "&* %&&+-$*&% #*% "& ./+$<&% .+(%/) #' '/3&)&% ( # '(l/3$l$! &' $" #&+9 RESULTS AND DISCUSSION
T"& +&#)$(* ( &+3/!l #l)("(l $" HCl ( !$&l% &+3/!l )"l(+$%& -#&' /'& ( "& '#3$l$! ( "& $*&+-&%$#& )#+3()#$(* "# $ll 3& (+-&%9 B#'&% +(- "& &*&+#l +&#)$(* '"(* $* F$/+& 1, "& */)l&(."$l$) "!%+(?$%& +(/. ( "& #l)("(l $' '$-.l! %$'.l#)&% 3! "& -(+& */)l&(."$l$) "#l(&* #(-9 A' '/)", "$' +&#)$(* $' )#ll&% */)l&(."$l$) '/3'$/$(*9 T"$' !.& ( +&#)$(* )#* .+&)&%& $* &$"&+ SN1 (+ SN2 +&#)$(* -&)"#*$'-'9 T"& SN2 +&#)$(* $' # 3$-(l&)/l#+ */)l&(."$l$) '/3'$/$(* ())/++$* # # '$*l& '&. -&)"#*$'- $"(/ "& (+-#$(* ( $*&+-&%$#&'9 I* "$' +&#)$(*, # */)l&(."$l& ##)' (..('$& #*% #&' #* &l&)+(* +(- C OH 3(*% "/' $;$* # +#*'$$(* '#& $* "$)" "& (l% .#+$#ll! *&#$;& HO C 3(*% $' .#+l! 3+&#$* (..('$& (
Figure "9 A++#*&-&* ( .(''$3l& */)l&(."$l$) '/3'$/$(* +&#)$(* (+ #l)("(l'
A' '/)", &+3/!l #l)("(l +&#)$* $" HCl $ll -(' .+(3#3l! /*%&+( SN1 +&#)$(*9 I $' #l'( "& +&#'(* "! "$' -&"(% (+' 3&' (*l! (* &+$#+! 3/ *( (* '&)(*%#+! (+ .+$-#+! #l)("(l'9 U*%&+ SN1, "& -&)"#*$'- (+ "& '!*"&'$' ( &+ 3/!l )"l(+$%& $' '"(* $* F$/+& 5 H C% 3&l(: -
Figure #$. P+((*#$(* ( OH +(/. 3! HCl
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T"& "!%+(?$%& +(/. ( "& 3/!l #l)("(l $' <+' .+((*#&% 3! "& "!%+(&* ( HCl l&#;$* "& )"l(+$*& &l&)+(* +$)"9 T"& .+((*#&% #l)("(l "&* /*%&+(&' # 'l(, +#&l$-$$* '&. ( '.(*#*&(/' %$''()$#$(* ( !$&l% # &+$#+! )#+3()#$(* $*&+-&%$#& #*% #&+ "$)" $' # ((% l&#;$* +(/.9 G((% l&#;$* +(/. l(&+' "& &*&+! l&;&l ( "& +#*'$$(* '#& "&+&3! $*)+&#'$* "& +&#)$(* +#& ( )#+3()#$(* (+-#$(*9 T"& )#+3()#$(* $*&+-&%$#& "&* +&#)' $" "& */)l&(."$l$) )"l(+$%& $(* ( (+- 3/!l )"l(+$%& $* # #' '&. +&#)$(*9 H(&;&+, "$' +&#)$(* -#! *( *&)&''#+$l! ())/+ $ "& (+-#$(* ( '$%& .+(%/)' $' *( .+&;&*&%9 I*'&#% ( 3(*%$* $" "& )#+3()#$(* l$& $* F$/+& 4), "& )"l(+$%& $(* )#* #l'( ##) "& "!%+(&* $* "& CH 3(*% '"(* $* "$' -&)"#*$'-: -
Figure ($. P+((*#$(* ( OH +(/. 3! HCl
T"& +&#)$(* $ll .+()&&% #' '"(* $* F$/+& 4# #*% 43, "(&;&+, "& */)l&(."$l$) )"l(+$%& $ll $*'&#% ##) "& "!%+(&* $* "& CH 3(*% #*% "& &l&)+(* ( "& 3(*% $ll 3& %(*#&% ( "& )#+3()#$(* ( !$&l% $'(3/!l&*& F$/+& )J9 T"$' $' )#ll&% &l$-$*#$(* +&#)$(* '$*)& "& "!%+(?$%& +(/. $' &?.&ll&% $*'&#% ( 3&$* '/3'$/&% $" "& )"l(+$%& $(*9 T"$' )#* "#..&* "&* "& +&#)$(* $' -#%& # # "$" &-.&+#/+& '$*)& "$' &*)(/+#&' &l$-$*#$(* +&#)$(*'918 A' # .+&)#/$(*, )(l% )(*)&*+#&% HCl '(l/$(* $' /'&% $* (+%&+ ( &*'/+& "# "& +&#)$(* $ll .+()&&% (#+%' #* SN1 +&#)$(* $*'&#% ( #* &l$-$*#$(* +&#)$(* $* (+%&+ ( !$&l% 3/!l )"l(+$%& $*'&#% ( $'(3/!l&*&9 E?)&'' HCl '(l/$(* $' #l'( #%%&% ( /+"&+ %+$;& "& +&#)$(* (#+%' "& (+-#$(* ( 3/!l )"l(+$%& ;$# L& C"#&l$&+’' .+$*)$.l&9 "&* 3/!l #l)("(l $' +&#)&% $" HCl $* # '&.#+#(+! /**&l, $ $' *&)&''#+! ( 'l(l! (.&* "& '(.)() +(- $-& ( $-& ( +&l$&;& "& .+&''/+& "# %&;&l(.&% +(- "& -$?$* ( "& ( +&#&*' '$*)& "$' .+&''/+& )#* (+)& "& '(..&+ (/ ( "& '&.#+#(+! /**&l #*% )#* #l'( -#& "& %+#$*$* ( "& l#!&+' %$@)/l9 28
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-#&+$#l9 B($l$* )"$.' .+(%/)& # '&#%! '+&#- ( <*& #$+ 3/33l&' "&* "&#&% $* # '(l;&*9 I .+&;&*' 3/-.$* +(- ())/++$* '$*)& "& '+&#- ( 3/33l&' #*% /+3/l&*)& .+(%/)&% 3+&#' /. "& l#+& 3/33l&' ( #'&' $* "& '(l/$(* 3&$* "&#&%9 I "/' .+(-(&' '-((" 3($l$* ( "& '(l/$(*9 B($l$* )"$.' -/' 3& #%%&% $* "& l$=/$% 3&(+& "&#$* "#' 3&/*, ("&+$'&, "& 3($l$* )"$.' '/%%&*l! .l#)&% $* # '/.&+"&#&% '(l/$(* $ll )#/'& "& l$=/$% ( 3($l # (*)&9 A' # +&'/l, "& '(l/$(* $ll '.l#'" &*$+&l! (/ ( "& #' ;$(l&*l!9 28 T"& )(*%&*'&+ $* "& %$'$ll#$(* '&/. .+&;&*' #*! -#&+$#l l(''9 #&+ )(*$*/(/'l! )$+)/l#&' $* "& (/'$%& ( "& )(*%&*'&+ #*% "/' "$' )(*%&*'&+ $' )#ll&% # #&+#)&&% )(*%&*'&+9 A' "& ;#.(+ +$'&' $* "& $**&+ /3&, "& #&+ )$+)/l#$* (/'$%& +&-(;&' "& "&# +(- "& ;#.(+ #*% )(*%&*'&' "&-9 A$+ #)&&% )(*%&*'&+ )#* #l'( 3& /'&% 3/ #&+#)&&% $' -(' &>&)$;& "&* "#*%l$* ;#.(+' "# #+& %$@)/l ( )(*%&*'& (+ '/3'#*)&' "# #+& ;(l#$l& l$& "& )#'& ( 3/!l )"l(+$%&9 T"& +&)&$;$* #' $' #l'( &. $* # )(l% #&+ 3#" ( .+&;&* 3/!l )"l(+$%& +(- ;#.(+$6$*9 28 T( &' $ "& (3#$*&% %$'$ll#& $' 3/!l )"l(+$%&, $ $' '/3&)&% ( '(l/3$l$! &' $" #&+9 Al!l "#l$%&' #+& #&+$*'(l/3l&, "/' *&#$;& &' +&'/l '$*$<&' "& .+&'&*)& ( 3/!l )"l(+$%&9 I #l'( &'' $ 3/!l #l)("(l $' (3#$*&% $*'&#% '$*)& #l)("(l $" l&'' "#* <;& )#+3(*' '/)" #' 3/!l #l)("(l $' +&l#$;&l! '(l/3l& $* #&+9 S"(* $* T#3l& 2 #+& "& (3'&+;&% .+(.&+$&' ( "& .+(%/) (3#$*&% "$)" #+& #l'( *&#+l! "& '#-& #' "& .+(.&+$&' ( 3/!l )"l(+$%& "/' P+(.&+$&' ( .+(%/) (3#$*&% Table 1:.('$$;& $-.l!$* !$&l%9
B($l$* .($*, C : C(l(+ : S(l/3$l$! $* H 2O :
50 "$&, (.#=/& $*'(l/3l&
O* "& ("&+ "#*%, '/--#+$6&% $* T#3l& 2 $' "& !$&l% (3#$*&% (+ "& '!*"&'$' ( 3/!l )"l(+$%&9 Y $&l% (+ "& '!*"&'$' ( 3/!l )"l(+$%& Table 2:
&$" ( 3/!l #l)9, 7970 : &$" ( B/Cl, 95 : T"&(9 Y$&l%, 971 : !$&l% 790 : T"& .&+)&*#& !$&l% ( 3/!l )"l(+$%& $' +&l#$;&l! "$" $-.l!$* "# '$%& #*% 3#)#+% +&#)$(*' #+& -('l! .+&;&*&%9 I #l'( .+(;&' "& &@)$&*)! ( %$'$ll#$(* #' # -&"(% ( ./+$!$* # '/3'#*)&9 H(&;&+, "$' +&'/l '$ll "#% '/>&+&% +(- ;#+$(/' &++(+'9 T"& l#''#+&' /'&% $* "& '!*"&'$' '/)" #' "& '&.#+#(+! /**&l #*% #'' -#! *( "#;& 3&&* #ll %+! #*% )l&#*9 T"& /'& ( 'l$"l! & l#''#+&' )#* $*+(%/)& #&+ #*% ("&+ $-./+$$&' "# )#* "!%+(l!6& "& (+-&% 3/!l )"l(+$%& (+ "$*%&+ "& '!*"&'$' +&#)$(* +(())/++$* "$)" )#* #ll +&'/l ( # l(&+ .&+)&*#& !$&l%9 T"& )(l% )(*)&*+#&% HCl '(l/$(* .+&.#+&% -#! "#;& 3&&* #ll(&% ( '#*% # +((- &-.&+#/+& 3&(+& +&#)$* $ $" 3/!l #l)("(l, "/' $'(3/!l&*& -#! "#;& 3&&* (+-&% #' $ll/'+#&% 3! F$/+& 9 A' '/)", "& HCl +&#&* ( 3& /'&% '"(/l% 3& &. )(l% #' .(''$3l& ( .+&;&* #*! '$%& +&#)$(*' +(- ())/++$*9 T"(/" "& .+(%/) +(- "& '$%& +&#)$(*, $'(3/!l&*&, $' ;&+! ;(l#$l& #*% )#* &#'$l! 3& +&-(;&% +(- "& -$?/+&, (+-#$(* ( $ '$ll l(&+' "& !$&l% ( "& '!*"&'$'9 I -/' #l'( 3& &*'/+&% "#
"& 3($l$* )"$.' #%%&% #+& )l&#* #*% +&& +(- $-./+$$&'9 L(('& '(.)()' #*% ($*' $* "& %$'$ll#$(* '&/. )#* #l'( 3& # '(/+)& ( &++(+ '$*)& $ +&'/l' ( -#&+$#l l('' #*% l(&+' "& .&+)&*#& !$&l%9 T( l&''&* "$', "& ($*' -/' 3& &&*l! '&)/+&% $" P#+#&) "& &=/$l$3+$/- ( "& +&#)$(*, +&%/)$* "&'& '(/+)&' ( &++(+' )#* "&l. $* $*)+&#'$* "& !$&l% $* '!*"&'$' +&#)$(*9 B/ $;&* "# "& .&+)&*#& !$&l% )#* 3& )(*'$%&+&% "$", "&'& '(/+)&' ( &++(+' #+& *&#+l! -$*$-$6&% "+(/"(/ "& )(*%/)$(* ( '!*"&'$'9 CONCLUSION
S!*"&'$' ( #l!l "#l$%&' $' $-.(+#* *( (*l! $* "& '/%! ( "&- 3/ #l'( $* "& <&l%' ( $*%/'+!, -&%$)$*& #*% #+$)/l/+& 3&)#/'& ( "&$+ .+#)$)#l /'&'9 T"& )(--(*l! /'&% -&"(% ( .+&.#+#$(* ( #l!l "#l$%&' $' "!%+("#l(&*#$(* ( #l)("(l'9 T&+ 3/!l )"l(+$%&, # &+$#+! #l!l "#l$%&, $' '!*"&'$6&% +(- &+3/!l #l)("(l "+(/" SN1 +&#)$(* $" HCl +#"&+ "#* SN2 3&)#/'& ( "& +&l#$;& '#3$l$! ( "& )#+3()#$(* $*&+-&%$#& (+-&%9 H(&;&+, # "$" &-.&+#/+& )(*%$$(*, &l$-$*#$(* +&#)$(* $' &*)(/+#&% #*% "/' 3/!l #l)("(l -#! #l'( /*%&+( &l$-$*#$(* +&#)$(* ( !$&l% $'(3/!l&*&9 T&+3/!l )"l(+$%& (3#$*&% $' )#+&/ll! %+$&% $* (+%&+ ( +&-(;& #*! #&+ "# )#* "!%+(l!6& "& .+(%/) 3#) ( 3/!l #l)("(l9 T"& (3#$*&% )+/%& .+(%/) $' /+"&+ ./+$<&% "+(/" +#)$(*#l %$'$ll#$(*
"$)" #&' #%;#*#& ( "& %$>&+&*)& $* 3($l$* .($*' ( "& $-./+$$&' #*% %&'$+&% '/3'#*)&9 T"& (3#$*&% .&+)&*#& !$&l% $' 7909 T"$' +&l#$;&l! "$" !$&l% '"(' "& &@)$&*)! ( /'$* "!%+("#l(&*#$(* ( &+$#+! #l)("(l' $* .+&.#+$* &+$#+! #l!l "#l$%&'9 I #l'( $-.l$&' "& &>&)$;$! ( %$'$ll#$(* #' # ./+$<)#$(* &)"*$=/& $;&* "& %$>&+&*)&' ( "& 3($l$* .($*' ( "& )(-.(/*%' .+&'&* $* "& '/3'#*)& ( 3& ./+$<&%9 I '"(' "# '(/+)&' ( &++(+ '/)" #' )(*#-$*#$(* +(#'' #*% 3($l$* )"$.' #+& *&#+l! -$*$-$6&% #*% #&+ $' -('l! +&-(;&% +(- "& +&'" 3/!l )"l(+$%& '!*"&'$6&%9 REFERENCES
18
M)M/++!, 9 200J9 O+#*$) C"&-$'+! 7 " &%9 C$apter 38< Or'ano$a!i%e&, C$apter 33< Rea)tion& o A!"#! Ha!i%e&< N*)!eop$i!i) S*&tit*tion& an% E!i+ination& = C$apter 36< A!)o$o!& an% P$eno!& 9 B+(('C(l&, C&*#& L&#+*$*: B&l-(*, .9 4, 4240 Q 19
28 P#;$#, D9, L#-.-#*, G9, K+$6, G9 #*% E*&l R9 15J9 I*+(%/)$(* ( O+#*$) L#3(+#(+! T&)"*$=/&'9 Part Fi2e< T$e Te)$ni:*e& 9 S#/*%&+' C(ll&& P/3l$'"$*: O+l#*%(, .. 57457, 12, 57, 59 48 Al+()"&, C9 A!"#! Ha!i%e&9 R/&+' U*$;&+'$!C#-%&*9 O*l$*&89 R&+$&;&% +1"9 +(-:".:)+#39+/&+'9&%/#l +()"&C"09.% #))&''&% M#+)" , 2015J9 8 S)$&*)&L#39 Materia! Saet# Data S)$&*)&L#39C(-: S$eet 9 C"&-$)#l' Q L#3(+#(+! E=/$.-&*9 O*l$*&89 ++#9 7
R&+$&;&% +(-: ".:9')$&*)&l#39)(--'% '9.". #))&''&% M#+)" , 2015J9 58 T"& U*$;&+'$! ( S!%*&! F#)/l! ( S)$&*)&9 E.peri+ent >?< O*l$*&89 +1"9 E.tra)tionR&+$&;&% +(-: ".':')$l&#+*9'!%*&!9&%/9#/! )"&-$'+!.+&l#3$-#&'E2&?
+#)$(*$-#&19$ M#+)" , 2015J9 8
#))&''&%
E+($% O+#*$6#$(*9 Si+p!e Di&ti!!ation Set0Up 9 E+($%9O+9 O*l$*&89 +1"9 R&+$&;&% +(".':9&+($%9(+#+)"$;&+ "(%$/-)"&-$'+!.$)/+&''%$' 9'&/.9$ #))&''&% M#+)" , 2015J9
A,,ei/
C#l)/l#$(* ( P&+)&*#& Y$&l%
wt of vial with pdct wt of empty vial −
wt of t butyl chloride x −
wt of t butyl alcohol x −
20.657 g −16.003 g =4.657
=
1 molt −butyl chlorid e
MW of t butyl chloride
4.657 g x
=
−
1 molt − butyl alcohol
MW of t butyl alcohol
7.780
=
−
gx
g : wtof t butCl obtained −
1 molt −butCl 92.562 g
1 molt −butOH 74.12 g
=
0.04873 mol of
t butCl −
0.1050 molt −but −OH
=
T"&(+&$)#l )(*;&+'$(*: 0.1050 molof
t butOH x −
1 molt −butCl 1 molt − butOH
x
92.562 g 1 molt −but Cl
=
9.716 g t − butCl =theoretical
A)/#l !$&l%:
amt of t butylClobtained x 100 theoretical amt of t butCl yield −
−
g x 100 9.716 g 4.654
=
47.90 : Percentage
=
yield
yield
