!"#$"% ! & !"#$"%'&(!"%)*+,-&(+*,'%*++-%+*+ . /0"#$%%&'% ( ) * + ( ,- ./,0)+ ,-)1 %2#3 4 515(5+251 %6,76-)(,7-)+6+ +#%3#%./ 8 9%#$ :.9!9% 9% %%3#%'%+*4%*+ 7 7 * , n O + → 7;7,5 2<=.9.4>$:9!?:9!67,?6,6@ ABCD9%6E6D)6;7,5D >$?6D6@ #%3#%'%+%-+'5%'%*+6%#%3#%'%*+6(%+*4%*+, "73+#%3#%8 n '%*+6(%+*4%*+, . /+0"#$-),F%&./G)(F 9H%#$.3 ;5 <!./4 *0)F1F)F,F2()F 6?6-)FF?-),F6-)*0F6* %*6-)*0F, 6*0)F . /94"#$&I%<J$/'/K./)(L ;/5 F) /24 + * 1 1 * 1 ( ,- ( ,- F , 2 F , + ,( MN4 n 6O;?5 6,O;,)(P,56)F6E+*1 92:#;<"=>%?%)@##%3A%&BC%* + '% + * Q7*O6E7 BLI4BCD9%6E66D . /D4"#$-),%&'% ( ) ( ,- ( ./-),(% -)*% R %S2&4 -)-G-)-,1-)-,-)-G -)-1-)-2-)--)-1 T6;S/#$56E6?6-)*?-),(6-)-GU S 6-),?-)-G% . /E0"#$&%VWJ$/'/K./,,)L ;/5G /2.XJ$/'/KY @1@S@2)@S FGFH%0 6 6EZ[$.XJ$S ;TWJ$/'/5 D2:#;<"=>%?%)I%)@##%3A%;J1! + ("7+,KLGM&"G0N%3%LGM0+ . /O0&S/\./]^_ >$%%>%.`/!.3a1_ 9 %S4 -),1-)-F-)-F2-) F S6_6-)-F% , EP#%3%0%* + 5% + *;<%#%3%(,'%* + 4% + * BL4 ?7;*?,5O6E7P, BCD9%6E6D%)6;P,5D% >$?6D?;P,5D6D6 6EP6O6O;P5 b/#$4 n 6O6O;?5 . /Q0"#$ZL;/5%X=L./ 2F)c<. 9H%#$/\.;5 ./(F<! Z2#34 +)0L1)(L ()(1L1*)*+L daef!4 1 * ( ( + 2 F 1 56*6-)(F%6E%6,G)1 6E6;F)?,G)15O,16-)*% 6E6?6-),F%6EZ6*)*+L MN n 6O;?56-)(FO;-)(F?-)*56*6E*( . /R4"#$ZL;/5,./,-)1 c<.>9H%#$>N< /]^dgF-)( 5Z2#34 *)*+L 1)(L +)0L 2()(1L 5%4 1*( (+ 2F,- 5Z/h.3h%>N6E%g6%7% 6-)+%)6;F-)(?,-)15O((6-)G% 6?6-)*%6EZ6-)*)(6+)0L 5MN46O6-)GO-)*6*6E*( SPT%U= !"#$"%3V%)%"/I.% iAj<.2'/ #$&#d/29k./>$I.% "229.$If d$/9%./.d 9%d W20P0+D-*+'5+*+'5%*+'+%+D !"K#(=>%?%)I%)+,+D-+'5+S +S-*+'5+*+'5%*+'+%+S&<%+S'%+D ? !"#$"%3V%)%"(X#%3A%"7#%3%, . /Y0&'% * + ) ( ) )/h..4 P "#$,./)(L ;/5 P 2'/#$<9H%=L ./4 )(L 1,),L *)*+L 2()(1L O#F3 !"K#"<%"<% !"#$"%3V%)%"!Z./9% h.l9^ /m2R% XlL 9% /J%a2 c^@S7n:,4,;S2I</d5 @7n:,4;2I<5 c<.Dm#c.2 %+*(3 !"K#!Z,'%+*(3,-%+(#&)# !"K#, . /0"#$-),%./-)% c<.2-),%$' /#$9% ./4 -)*1-)(-)F2-)+ FGFH%0T26En:,4 6E66-)% 6E;2/#$56;/#$576-)(% Q2:#;<.%[%)F\%];<[%)F\%]!F%)$8%"73GXU%)&"G!F%)$8%^ 7b%.!&4 hh hh m M n = 7R.$If4 X Y co C H n n n = 7R.$If.4 CO hh n n n = U , n a n b n a b + = + /24 , ) 9.$If!>,)> )9%!>,)> I>$`a/#$ o/A:4b9.$If. .X!9.$If>29% . ZT4 n 6,)FU)FU*)F%,6% l]2,9o#4 n 6p)+0UA n )** n 6p)U n 6p)1&qr%X9>,UU*U( $I%/n:%!> ZT n 6,)+0,6,)6 6E,)+06;75O;75-)+06-)**6 a9%>69%>, _`0#%sS=L!>I<. ZTb%/ n 6,)+06EsZ>2^>;a65 6+0s6EsZ>2t6, ?+06**s c[>$sZ>2^>9)+0ut>`// ZT n 6p)*;&p2=,AA*p5 sZ2^>6*-s6EsZtl60-s c<./hLsS]n:9% ZT4I<%/ n 6,)+0 6En:%6;`%I5,6()6+ 6Es(6,+O;,+7156,+O;,+7156)s 6Es+60001s . /+0&/'/KI<2()1=Lla!&,,) L;/5daef4 ( ) + 1 + ) * 1 1 * 1 ) ( ,- 2 ( ,- ) F , FGFH%0BC7;.5 ()1 (G)+ -)F hh M = = 6E,( n 76(G)+6E n 6*)( 6E * 1 ( ,- * . /D4,(&S/'/KI</\..3^_ >$%%>%.`/! a+(_ ,daef!#S4 ( ) * + 1 * 1 ) ( ,- ( ,- ) F , 2 F ,- ) + , v:9%S&4 ,414,4*2,4, R.$.[4 n:S4_6,4,));.5 6ES6_6-)(% ,( *F -)( anken M = = U6E ,( *F )Fn n= → = 6E"24 ( * + >$6)F>$;7*5O6)F;.X5 6E(6*+6En:,4, . /E4"#$=L<<.J$/'/K./(1)( 1)1 Q g%=L%&4 G-s),-s 11Fs,Fs 1-s)-s20FsFs 6,),%)6,)+%6EE4;2=d2w/5 6E n 6O;?56,),O;,)+P,),56)6EsZ>2^l;a*56-s6EsZctl6 1-s Ra%)bF%c@#cK?#NN*(%J%d, e%%<$a!U"+=e%A[A %+%-+f+#4&(?,& /29I</L9.6;97?95O ;MN]x/ZT*(2c<. #Nw%/65 %92%a;ZT4,))*2%5 ;a4?)PP))p5 ZT4>(+t2%^YMN96;(7?+5O6 ZT4\.#!.4y.22%a 7P?%;5% c<..d246E6- 6E4%+%-+4&(*,&A7% c<..d2,;S5AI<;5$I/ P;J !"#$"%83V%)K%K&?0a%)bF>G<%+%-+4+# W20da!.)*2%4 P*;5 17,;5* zP,;5* 27;5* MN*2%6E%6*).6E6-) 6E47P*;5*6E W2+0daef\.#!.2%2,I</dY 7 1P g 2P, {.2%6E%6)2,I</da,6E6, 47?,?;566E W290>9VD/la)2,/dY;B|D25 gP, 17, 2 @D/la6E%6,),/d6E6, 6E7PP,;56P,;56E@ 1<H=;H% /%)0 ( 1<4y.a2%\.#Y 1<+4y.*a2,%\.#Y 1<9%9#>9.4+,-U1,(U G,-;+F*5;ZuS}S2(2,5 1<D4y./la;B5%\.#Y ;P%5 1<E4~%V2a%XI</defbef!~tlF1/ daef!~4 g( 1(;5 *+ 2*+;5 Y>%?%)@#hXUF `,-%/9.4 Py.4%+%-+4&(*,&"7%+%-+*&(&G<[?, "=|d/2.:! _[ %hXUF'%+*4%*+N%'%*+6(%+*4%*+,(KiG< n , ;bdfZ<Q'%5 Py.d)2,;BS54%+%-+f+f&(*,&'%+%*& BS'5%*+'%+* fy.d)2;B54%+%-+fDf&(*,&'%+%f+*& B6E%hXUF'%*+4%+*N%'%*+6(%*+4%+*, W2D0"#$&./'/K2W9%.)./Ll^2n:% 46*4(_<ef,>+da.Y (*1 1)+*1 g+(,- 2(+ = /%)0%+*5%*+'5!XUF%" n 'O;?56*O;(P*56*6E W2E0b/#$%X/a./^LSn: % 4 % ((4 0= d aef!4 g+ 1(1 *1 2F,- %4%6((406EO6O*6E;y.E5 6E6O;?56O;*P566E 2:#!\%=>%?%)%XJ@#!XUF%"j%?<%#%3A%•%#% A'%!XUF ;9.$If d$/Z[$/./Sla9% .5 W2S0%S$/h.. Q,4%/#$•)(L ;/5 Q4%#^S$S)"#$S$S•%% %2#34 ,)+1,)1,)(2,)F FGFH%0%*+(3!XUF,'%#%3A%(3!XUF,'YN&"G i/#$S66-),%6E%6,)1 +P+ckFjN=l%]Km%)[%)F\%]NXUm%)[&"G* + 8+ckFj&#%) m%)[&"G W8[&"G*+GFV%'[(!"%)ckFj,"GkFj W20+E*'5+*+;<+S'5+*+ W2O0"#$% F /-)% "#$+*/-)% % F #N^+ * ;2 R (/ D) - B9f6, s5/%S9S2#34 ()(11)1,*)2,0)+ FGFH%0%+E*'%9**'6+%*+'YN&"G 0n$<#o(K[#Fa%)bFj%C=e%A[A, '5%+E*' * F -), -),11 1)1 CH COOC H este n mol m c g = → = = = F 92:#!\%=>%?%)#%A%"Nj%?"[&"G* + '[&"G + *%A )H xt+ → !XUF - )O t+ → p%)"[&"G* + $q%)[&"G* + 3#%Ar%[&"G + *@#!XUF8%sFj% &"G + *!Ij%$q%)[&"G + tI%);<"#% A(e%%<)%)=e%O, %+*(!XUF,'%+*("7%*+3#% A,-%+(3=>%?%);J#% A, W2Q0"#$&/S)/la./-)(% 2/S$-)% ./&.)/la"#$&.9% ./4 -)(%1-)+%-)1%2-)*% FGFH%0MNI676-)(7-)6-)+% D2:#;<=>%?%)!%))Xj%)(k%)cK)*, >%?%)@##% A0LGM)k##% A;J)'0+%(;J%G<[)*W2+E(*,+'5K+) *, '5% * 0% ) '0DN4fK+)*(+ViM%+), * %hf*0%)'0+(!Xu%)U=K%K&*, W2R0& /\./]X.2T€X&./.9.a ^/=Nl>t#>2=/)>$g,,)1{>$ #N^@c * Oc * ./,)+@b * a !4 1)*1G)*,-)*2,)-* FGFH%0P7 - Ni t → * ; * CH OH HCHO m m+ 5a,,)1 n:%•4^6,4( , , ,)+ -)-F ( ( ,-1 HCHO Ag n n mol= = × = % 6-)-F*-6,)FU * ,,)1 ,)F ,-)* CH OH m g= − = W2Y4&'%-),%-)%#N<^@c * Oc * @. /4 ,-11,-)1,+2,)+ FGFH%0 -),%P•-)%@ -)%•-)1%@ •@6,%6E"##@ E2:#;<"V%)?.%[AA#"!#vT%U=!XUF"7 :#;<"Pw1w W24".&F./la^ R (/ ),(- - 9SS./4 ,-1,,F2,0 FGFH%0MNda4 ; ,5 x x + SS•./,FSS W2+4".,*)1&'%*./la^ R ( /A),(- - •&#SS29% .2 ,,,)R%%&SS4 -),%1-)%-)*%2-)(% FGFH%0".&*.+SS S"{_b{4% . 6% SS 7 H O m + • H O m 6,*)1?,,,)6,)+ T ,)+ ,) ,1 ete H O n n mol = = = ⇒ ∑ ∑ %&SS 6 ,) -) + mol= S2:#;<"=Xj%)==x%))>&3GXU%)0 c.$I‚4T]9]g%.$=`>$9>#/=D#/3,& $,> N=4T]%9]$/h!,%@•,%_A.$=`D%@•$%_;^D) $n:e a5 %9]$/t;@•_5SV}%#>%a.$=9H%`/2L /9%#>%a "^.4~ƒa!.^b4 ; 5 ; 5 x x x R OH xK R OK H+ → + Ay7b•yb7 , S>$4a,%.#N^b,%%.g49R4'9Q) Z[$<./h!.!%.2=L/9%!.) ` /2D#/3QlN "^/S4Dƒa#l!/S y?7@ - * )NH t → y?7@ S>$4a,%/S/S%#l•,%D ⇒ ∆ &'DE4+R'S)Z[$<./h &#%AN&#oy%#%AN%) y#%A "^D4~ƒa^h% y;5 D 7Dc•y;c5 D 7D Ay7c•yc7 ,%•,%y ∆ & ↑ '++) "^S9S4DƒaDu2 yy „ 7c•yc7y „ ,%•,%y ∆ & ↑ '+94 h z "^%D4Dƒa^ PyPc 7•PyPc * ,%•,%y ∆ & ↑ '9SNE) W290-),F&D/la#N`/!^c * ./ZL ;/5 %.d./1)G+%.B#3!Z4 ()1(L1()(1L)(L2)(L{b<\.# R.$.[4BCda.!D4 R COOH− Q.4 R COOH− 7c * • R COONa− 7 ↑ 7 S4%•%,% ⇒ ∆ &'+(+9f,'DD) S/h4GXU%)x%)0+QNRS4+YNE'QNQ) •R% 6 1)1, -) (( mol= •=L 4Z6-))(6()(1L W2D0,-&./la<<.J$/'/K#N`/!^c% ,()(>‚ZLL ;/5Z2#34 ,),L1)(L*)*+L2()(1L FGFH%0+yP7c6Eyc7 Q% % ,% 0 %g66(( A"eF$<3GXU%)x%)'DND4Y'DND) %+'DND6DD'YN&"G'5W'+N+DG. JXu%)G<&A"|p%)Xj%):%X!\%%X%)3V%);} <yP6Eycig++) i%g6()(6EyP6yc6-)% in:•yP^4,6E6,OyP6-),% O2:#;<"Pw1;<Pw1w0 P#a2C)#>%a !#9H% -1y-2 & -& 1 '& -& 2 P BC% #>^a i R #>9.a TWa`/!$u>€24% 6% R PRfN.$Ia#$4 b/#$,>@;)5 ; 5 ; 5 ; 5O CO O H O O O pu n n n+ = • ; 5 ; 5 ; 5O CO O H O O O pu m m m+ = B9f/#$>•.l@;))5 @7 • 7 24 O CO H O mA m m m+ = + Z^% @ 6% 7% 7% W2E0"#$%%&…4 + ) * ( ) ( 1 ./,)G1 F)0+ L#3 %Y;"#94(),15 W2S4)1*&./la#N`/!^c#-)1G+L ;/5%%%. B#3!%4 F)(G1()GFF)G(2()FG W2O4()&'%.S$)S)D†%#N`/!^c>$#-)+0L ;/5 ,d./&‚~b!~4 )FF1F)FF)F2F)-F FGFH%0*>I/h.2,.$If/X•R%c6 6-)-*6--+% = /%)Pw1w0 y& ~ '&T%U=-&+'DN+-YNYS+94YNY9+'ENE+) "7 m%)x%))>&3GXU%)&~'&T%U=-&x%)'DN+-YNYS(+9f,'ENE+ W2Q0&/S/la% .4 Q,4"S%/#$./,)-1 Q4#N^ ;c) - 5.&@"S%@/#$=L ;/5./4 ,)(*(L1,)((*L,)*((L2,)(((L R.$.[4Z/S/laI9% 69d% 6-)-+% • ; 5 ; 5 -)-+ CO P C P n n mol= = S_c_b{24 ; 5 ; 5 -)-+ C P C A n n mol= = • ; 5 -)-+ CO A n mol= • )(-)-+ ,)*(( CO V = = L W2R0#^`&…'%.@)_/&~'%#S†c<./#$ …./-)++ Z[$/#$~ 4 -)G-*1-)*G-)G(2-)G* ;"#$.56;/#$S56;/#$S56-)-,F% %6-)-,F;((7,156-)G* 1 . t → y?7@ S>$4a,%/S/S%#l•,%D ⇒ ∆ &'DE4+R'S)Z[$<./h &#%AN&#oy%#%AN%) y#%A "^D4~ƒa^h% y;5 D 7Dc•y;c5 D 7D Ay7c•yc7 ,%•,%y ∆ & ↑ '++) "^S9S4DƒaDu2 yy „ 7c•yc7y „ ,%•,%y ∆ & ↑ '+94 h z "^%D4Dƒa^ PyPc 7•PyPc * ,%•,%y ∆ & ↑ '9SNE) W290-),F&D/la#N`/!^c * ./ZL ;/5 %.d./1)G+%.B#3!Z4 ()1(L1()(1L)(L2)(L{b<.# R.$.[4BCda.!D4 R COOH− Q.4 R COOH− 7c * • R COONa− 7 ↑ 7 S4%•%,% ⇒ ∆ &'+(+9f,'DD) S/h4GXU%)x%)0+QNRS4+YNE'QNQ) •R% 6 1)1, -) (( mol= •=L 4Z6-))(6()(1L W2D0,-&./la<<.J$/'/K#N`/!^c% ,()(>‚ZLL ;/5Z2#34 ,),L1)(L*)*+L2()(1L FGFH%0+yP7c6Eyc7 Q%. ; 5 ; 5 ; 5O CO O H O O O pu n n n+ = • ; 5 ; 5 ; 5O CO O H O O O pu m m m+ = B9f/#$>•.l@;))5 @7 • 7 24 O CO H O mA m m. .4 Q,4"S%/#$./,)-1 Q4#N^ ;c) - 5.&@"S%@/#$=L ;/5./4 ,)(*(L1,)((*L,)*((L2,)(((L R.$.[4Z/S/laI9% 69d% 6-)-+% • ; 5 ; 5 -)-+ CO P C P n n mol= = S_c_b{24 ; 5 ; 5 -)-+ C P C A n n mol= = • ; 5 -)-+ CO A n mol= • )(-)-+ ,)*(( CO V = = L W2R0#^`&…'%.@)_/&~'%#S†c<./#$ …./-)++ Z[$/#$~ 4 -)G-*1-)*G-)G(2-)G* ;"#$.56;/#$S56;/#$S56-)-,F%