ࡱ> O%` y)bjbj"x"x a=@@ %XXXl44444h,lKJ%%%(K*K*K*K*K*K*K$MhOdNK9X%"%%%NK_K% 8X(K%(KFD@XJ p_'641LH&J4K0KBHfO}LOLJOXJL%%%%%%%NKNK%%%K%%%%llld d llllll Problem Set Exam 2 Provide a complete detailed mechanism for the following reaction (including initiation, propagation, and termination steps). Remember to use fishhook arrows! hv H3C-CH3 + Br-Br( H3C-CH2Br + H-Br Using the BDE table on p. 134 in Wade, calculate H for each of the propagation steps Draw a reaction-energy diagram for the propagation steps from part a. Label H for each step, Hoverall, and the rate-determining step. Is the overall reaction endothermic or exothermic? 2.  Circle and name each functional group in the following structure. Indicate each stereocenter with an asterisk and determine the number of stereoisomers possible.  Hydrogen abstraction with bromine radical is generally very selective. In each case, draw the radical that you would expect to be formed.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Label each molecule as chiral, achiral, or achiral/meso. Label each stereocenter as R or S.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Consider the reaction below  EMBED ChemDraw.Document.4.0  Draw all possible products that you would expect from the reaction above (ignore stereoisomers). Indicate chiral centers with asterisks in all of the products. Predict the product of the following reaction, and provide the mechanism for its formation.  EMBED ChemDraw.Document.6.0  Draw a picture of the transition state for the above reaction. Pay attention to stereochemistry! If the same molecule were heated in diisopropylamine ((CH(CH3)2)2NH), would you expect the same product that you drew in part a? Why or why not? (Bromomethyl)cyclohexane undergoes the following two reactions:  EMBED ChemDraw.Document.6.0  Provide a detailed mechanism for reaction (1). Provide a detailed mechanism for reaction (2). Draw reaction-energy diagrams for the reactions. Clearly label starting materials, intermediates, products, and the rate-determining step for each reaction Label R and S stereocenters on this Fischer projection below (3 points) AND redraw in zigzag formation. Then convert the zigzag into the newman projection with Carbon 3 in the front and Carbon 4 as the back carbon  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  If a sample has a specific rotation [(] = 60 and a pure enantiomer has a specific rotation [(] = 150, what is the % of each enantiomer? In addition to providing products, also describe each of the following reactions as SN1, SN2, E1 or E2.  EMBED 1          " # . / L N    rk``h _hUtB*ph h _hb|#h _hb|5B*\mHphsH# jh _hb|B*mHphsH!h _hb|B*EHmHphsH$h _hb|B*EHH*mHphsHh _hb|B*mHphsHhUthb|6B*]phhUtB*phh _hb|5B*\phh _hb|B*phh@ hb|# . / L N h j $a$gd _^gd _ & Fgdb|gdb| & F7$8$H$gdb| 7$8$H$gdb| $7$8$H$a$gdb|$d7$8$H$a$gdb| & F7$8$H$gdb|$a$gdb|S)x) $ 8 b % & ' E F G H I J K i j k l n β㧜|ΕncUjL h _h _UVj'h _h _UjL h _h _UVjh _h _UjL h _h _UV h _h _jh _h _Uh _h _B*ph jh _hb|UmHnHujh _hb|U h _hb|h _hb|5B*\phh _hb|B*ph"h _hb|5B*EHH*\ph % & I J m n 1TU 8h^8`hgd _ & Fgd _gd _ 7$8$H$gd _ & F7$8$H$gd _ & Fgd$]gdb| 12PQRSXYZxyz{} !^_rs⻰◌qi\hUthUtOJQJ^JhUtCJaJh _h _5B*\phh _h _B*H*phj^ h _h _UjizL h _h _UVh _h _B*phjh _h _UjȇA h _h _UVjh _h _UjL h _h _UV h _h _jh _h _Ujgh _h _U"UXY|}rs 7$8$H$gdUtgdUt & FgdUtgdUt h7$8$H$^hgd _ & F 7$8$H$gd _gd _ & F7$8$H$gd _h^hgd _47:;ǼǼǼǼǼǼyqjbhShS\ haBhjJ@hUj@L hUVj`:hUjL hUVhjhU h5CJOJQJ\^JaJhh\hUthUtB*phhUthUt5B*\phjbhUthUtUjuL hUthUtUVjhUthUtU hUthUt%  :;~ $7$8$H$a$gd & Fgd$] 7$8$H$gd & F7$8$H$gdS "{&#$/gd 7$8$H$gd & F7$8$H$gdh^hgdUt & FgdUt 7$8$H$gdUt & F7$8$H$gdUtRS}~(((((((;(<(=(>(@(A(_(`(׺}ujj/L hrxUVj`hrxUjL hrxUV hrx5CJ OJQJ\^JaJ jNhrxUjL hrxUVUhrxjhrxU hS5CJ OJQJ\^JaJ h$]5H* h$]5h$] hSh h\ hhShShS\ jahShS&ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Provide structures for the following alkyl halides. 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TTXt`@UU@ LPH8 % &% 6 % &% (    % ( '% &% 6   % ( '% ( &% 6   % ( '% ( &% m6m   % ( '% ( &% T6T   % ( '% ( &% ;6;   % ( '% ( &% "6"   % ( '% ( &%  6    % ( '% ( % j%  % ( % j% j TTqz@UU@jLPO? % &% |z6| % &% (  j % ( '% &% z6 j % ( '% ( Fl]CDIFVjCD0100ChemDraw 8.0.3_hyL` g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`T$$_hyf@ K+7f&XYfX#`CH3@3 L7DB N7D` P01Io R01   I T+7?0(X(rc#`NH2 N}` V+7,5\_hy\[̤d# `O @o X7@ Z#+7f&<N<f&<#`Br M  O  Q  S   U    W  Y   [  ^kAyS@ \@ ]+f&hYhL3# `C@# _D2 a7Uvn4vB{SFvB9 AGvB{S BJvBs9 C K DJFH EFGR+h.^h.RS#`CH2CH3;2 c+7y!h.Th.y@#`CH3k k e7Vj2=G:MGs FNj2= GPDn H Q IPMR JMNka#kAOka#`CH2CH3vk g+7\ka-kka#`CH3 ^ ` b  d  f  h &YhjL`%@u i+7f&hyYhjLhy#`OH'@{ j)@&v l014*,+@9q n016,.-@Ll p/@`g r+7f&`Y`L`#`OH1@{ t+7f&YL_# `O3@&v v+7f&&Y&L&#`OH5@9q x+7f&9Y9L9#`OH7@Ll z+7f&LYLLQ# `O( k'% * m)' , o+) . q-+ 0 s/- 2 u'14 w)3 6 y+5 8 {-7F DMHCGRTS!<  x (XP`5 .i=5j !=l=#Dn %Lp='Tr5t !=v#Dx %Lz  \ d] _ ac ce1cgK L 7N P R T VX Zkmoqsuwy { ^ ` b d f hMOQSUWY[OHOHOOHOH O C CH2CH3CH3CH2CH3CH3CH3NH2OBr ``  ^| P a| `` ' '(1 `` F ``   j " `` "F"$" ``  $ j$ % ``   :  ``   3  `` B ``  . ^ `` 8 `` .^ ``   K > ``  @ |@  `` .  . ArialTimes New RomanF|pMDLSKXY Ariald 0!%b YCD!% `DD!% &D'D!% qD'D!% DOD!N%b 0DOD!O% qDxD!% DD!#Br% 0DD '  ' (.  '  ' )< '  ' (  '  '  0 !% `ED!% #ED!% 5ED! CH2CH3!% CED!% ,TESD! CED '  ' "4 CH2CH36=  @?E'D< !%b @?E D! CH2CH3!% \ED!% ~DĕD! 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C  TTxB@5'@C LPH8 % &%  6  % &% (  C  % ( '% &%  6  C  % ( '% ( &%  6  C  % ( '% ( &%  6z  C  % ( '% ( &% s 6f  C  % ( '% ( &% ] 6R  C  % ( '% ( &% F 6>  C  % ( '% ( &% / 6*  C  % ( '% ( % U%  % ( % U% U TTRZB@5'@ULPB8 WU TT[^B@5'@WULPr % &% $i6Ui % &% (  WU % ( '% &% '6R WU % ( '% ( &% *6P WU % ( '% ( &% -6M WU % ( '% ( &% 06J WU % ( '% ( &% 26G WU % ( '% ( &% 56D WU % ( '% ( &% 8 6A  WU % ( '% (  % ( % &%  6  % &% (  WU % ( '%  % ( % &%  6'?  % &% (  WU % ( '%  % ( % &%  6  % &% (  WU % ( '% &% '? 6u  WU % ( '% (  % ( % &%  6 % &% (  WU % ( '%  % ( % &%  6 % &% (  WU % ( '%  % ( % &%  6  % &% (  WU % ( '%  % ( % &%  6  % &% (  WU % ( '% % B%  % ( % B% B TTM VB@5'@BLPO?  TTX `B@5'@LPH8 % &% 69 % &% (   % ( '%  % ( % &%  6n  % &% (   % ( '%  % ( % &% n 6} C  % &% (   % ( '%  % ( % &% } C 6  % &% (   % ( '%  % ( % &%  6  % &% (   % ( '%  % ( % &%  6  % &% (   % ( '%  % ( % &%  6  % &% (   % ( '% %  %  % ( %  %   TT/b7qB@5'@ LPC8   TT8b:qB@5'@ LPl % &%  6  % &% (    % ( '% % P % %  % ( % P % % P %  TT"$1B@5'@P % LPC8  %  TT&"(1B@5'@ % LPl % &% n 6n 6  % &% (   %  % ( '% F, CDIFVjCD0100ChemDraw 8.0.3 ZH g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`D$$PN՚UPPN՚UPGѓ HyTh I7 : K7!e-w4 M"4ѓ O# K R7+4 U+7PNA #`OH$ J % L  & N ! '' P" &( Q!" ) S!# * T# , V"+ < Z9Ƀ9)* 67;G* 701LEF=VD 87?G&^ 901NGHA)&^ :7CD ;01PIJKV B+7fYR Z#`OHMV9x D+7fY9tR9t Z9Ƀ#`OHOD F#+7f7A7Af7K#`BrE <9; F =;= G >=? H ??A I @AC J AC9 L C;K N E?M P GCO 0dRMH-M W/3 X1nC; Y733`b Z75MxS [779Dzp \7?E b7- @ d-? B f/A FTFDMHCGRTSD`x  x (XP`5W :XYZ[_\h!Qc :e4W6W7^8f94f:^;OB mD^FHI*K<MORTU]^_`abdf < = > ? @ A C E GJLNPQSTVClClOHOHBrOH `` ! ! ! `` V  `` iq ``  i  K `` a `` ArialTimes New RomanFMDLSKXY Ariald 0 !% cELE!% ! ETE!% W EDE!% E_=? H ??A I @AC J AC9 L C;K N E?M P GCO 0dRMH-M W/3 X1nC; Y733`b Z75MxS [779Dzp \7?E b7- @ d-? B f/A  !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.4.09qVjCD0100ChemDraw 4.0.1Untitled d_1099417615E"!mA. ^'6^'6Ole CompObj~ObjInfoCONTENTS_1286437481!mA. ^'6^'6Ole EPRINT #Gocument-1i,b2  &5 +$$$$xx  `  xrL4g(rd'`Times New Roman   '                {   m       _  NBS/light) VjCD0100ChemDraw 8.0.36FG 4 @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrlY'] EMFG* ,p  5 ] 6KRpTimes New Roman|8|($" 4,|||x%||:|p\"`  |HMx:"X:|||||:|dv%   &% L_6LY % &% (  [  % ( '% &% jp6jG [  % ( '% (  % ( % &% LY6$ % &% (  [  % ( '%  % ( % &% $6Y % &% (  [  % ( '% &% $6G [  % ( '% (  % ( % &% Y6_ % &% (  [  % ( '%  % ( % &% _6$ % &% (  [  % ( '% &% p6$ [  % ( '% (  % ( % &% $6L_ % &% (  [  % ( '%  % ( % &% _6 % &% (  [  % ( '% Rp8"Arial % :|||x%:|# Dht#n#h:n#Xn#x:X:L|||||:|dv% %  % ( % Rp"Arial M MȻ:p3:|X:||||:|dv%  TTgo8@@LPB8  TTor8@@LPr % &% % ( 6% % V4go0% % &% 6_ % &% (   % ( '%  % ( % &% _6 % &% (   % ( '% % A%  % ( % A% A TT<K8@@ALPC8 } TT<K8@@}LPH8 % Rpj"Arial|P3'DQ|: (%h|:r|X3'O`:@x:'OLO  4|6'<&P3'h:P3'XX3':X83:<||||:|dv% Rp"Arial|8|2|||D:2|H:M\: %δMb@2H M MȻ:Hs*#X:b@||||:|dv%  TTBN8@@LP3& % % &% 69I % &% (   % ( '% % h%  % ( % h% h TT8@@hLPC8  TT8@@LPH8 % % %  TT8@@LP3:& % % &% 6 % &% (   % ( '% % y%  % ( % y% y TTds8@@yLPC*8 y TTds8@@yLPH8 % % %  TTjv8@@LP3& % % &% _6, % &% (   % ( '%  % ( % % % V0C=PDm L a$ L 6m L% % " K6zK% % V,@EA$ PyPyH$ H% %  % %   % '% % .%  % ( % .RpTimes New Roman @Mx:%:|X: ||||:|dv% . TT#58@@.LPKK % &% % *sq% ~6|6% ( %  %  %   TT""48@@ LPOK Q  TT#"-48@@Q LPCE   TT-"148@@ LP(   TT3"=48@@ LPCE   TT="G48@@ LPHE % RpLTimes New Roman|8|2|||"$h|8|2|||# # % %x-N# dxXMx:%|X(:,#$||||:|dv% ? RpTimes New Romanw(wMw:w!rZ(|xHMDx#M\:$δMf@?0H  Mx:u*"X>:f@||||:|dv% ?  TTI(N68@@? LP3& % % e % e  TTO"S48@@e LP) % %  %   TTT(Y68@@ LP3& % % & % % *q % 6% ( % % %  TTM_8@@LPHE  TTM_8@@LPOK %  TTM&_8@@% LPCE h  TT'M+_8@@h LP(   TT,M6_8@@ LPCE   TT6M@_8@@ LPH|E % %  %   TTBTGb8@@ LP3& % % 9 % 9  TTHML_8@@9 LP) % % [ % [  TTMTRb8@@[ LP3& % % F z CDIFVjCD0100ChemDraw 8.0.36FG 4 @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$l6FsZigF K7kF L7m{` M7o&vz N7qg&vz OsX{` P7{X9q W01~|}:9q Y#+7ff>969ff>9#`BrgLl [X`g ]gsb _+7ffkscsfmsZ#`CH3:`g a+7ff>`6`f@`_#`CH3Ll c+7ffLԪLԪfƋLd#`CH3u Qik zvv Rkm w Smo vxx Toq y Uqs x|zz Vsi | Xq{ ~ Z{}  \{  ^  `  b  d jI\U YU f+!7Y@2P\f# KN@@V@ g!  jIj \GT h76ev7r 9+!vlev4 #`@O-T :T ;6 <T7 = > ? @ A?Y2O\G#`OC(CH3)3N@V i!  TpDd2|wB[uD  j7[WDhD)[D  B+!BD TuD hD #`OH[uD  C[uD D[WD  E[uD) F G H I J!zDTpDd2|wB#`HOC(CH3)3@e@@@e@ e   F(DMHCGRTS)[  x (XP`5Ue'cci'g +jhfK nL M n N OP W Y []_a n cQRSTUV X Z \ ^ ` b d HOC(CH3)3OC(CH3)3K Br CH3CH3CH3 ``   3 `` >1  M>M ``  RC R  `` cgg `` `C` ``  X  X ArialTimes New RomanFhZMDLSKXY Ariald 0!% @0D`D!% @0DD!% 3qDD!% DD!% D`D!% 3qD@]D!% D@]D!#Br% D@D!% _D`D!% 8D@]D!%b } E`D!%b 8D@D!%b _DD ' (.  '  ' (.  '  ' (.  '  '  ' )< '  '   '   '   '   0!K% E_UD 0! OC(CH3)3 !O% "0E?D!% "0ESD!% bESD!% "0ED!% BESD '  '  '  ' "4 OC(CH3)36= "0ESD< 0! 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TpDd2|wB[uD  X7[WDhD)[D  /+!BD TuD hD #`OH[uD  0[uD 1[WD  2[uD) 3 4 5 6 7!zDTpDd2|wB#`HOC(CH3)3@e@@@e@ S    lppf EMF 2EPRINT#%PTuObjInfo&CONTENTS_12864462306)!mA. p_'6p_'6&%'l?; EMFTu ,p     *KRpTimes New Roman|8|($" 4,|||x%||:|p\"`  |HMx:"X:|||||:|dv%   &% ?6? % &% (   % ( '%  % ( % &% ?6~ % &% (   % ( '%  % ( % &% ~6 % &% (   % ( '%  % ( % &% 6 % &% (   % ( '%  % ( % &% 6 % &% (   % ( '%  % ( % &% 6? % &% (   % ( '%  % ( % &% 6 % &% (   % ( '% Rp8"Arial % :|||x%:|# Dht#n#h:n#Xn#x:X:L|||||:|dv% '%  % ( % 'Rp"Arial M MȻ:p3:|X:||||:|dv% ' TT-<Ǖ@A@'LPB8 ' TT-<Ǖ@A@'LPr % &% v6 % &% (  ' % ( '%  % ( % &% J6J % &% (  ' % ( '%  % ( % &% J6"M % &% (  ' % ( '%  % ( % &% "M6 % &% (  ' % ( '%  % ( % &% 6 % &% (  ' % ( '%  % ( % &% 6"Y % &% (  ' % ( '%  % ( % &% "Y6J % &% (  ' % ( '%  % ( % &% Y6 % &% (  ' % ( '% % %  % ( % %  TTǕ@A@LPB8  TTǕ@A@LPr % &% 6Y % &% (   % ( '%  % ( % % % V0?F`^ s^ H`^% % ^6m^% % V,BCblblZZ% %  % %   % '%  % ( % % % V08C8% % A6% % V,CC% %  % %   % '% % %  % ( % RpTimes New Roman @Mx:%:|X: ||||:|dv%  TTN`Ǖ@A@LPC'E  TTN`Ǖ@A@LPHE % RpLTimes New Roman|8|2|||"$h|8|2|||# # % %x-N# dxXMx:%|X(:,#$||||:|dv% !RpTimes New Romanw(wMw:w!rZ(|xHMDx#M\:$δMf@?0H  Mx:u*"X>:f@||||:|dv% ! TTUcǕ@A@!LP3& % % F% F TTN`Ǖ@A@FLPCE  TTN`Ǖ@A@LPHE % % %  TTUcǕ@A@LP2& % % %  TTN`Ǖ@A@LPOK ? TTN`Ǖ@A@?LPHE % % % %  TTǕ@A@LPCE  TTǕ@A@LPHE % % 7% 7 TTǕ@A@7LP3& % % \% \ TTǕ@A@\LPCE  TTǕ@A@LPHE % % %  TTǕ@A@LP2& % %  %   TTǕ@A@ LPOK % &% % *m3l% xO6O% ( % &% &% & TT+=Ǖ@A@&LPh, :& TT+=Ǖ@A@:&LPe, g& TT+=Ǖ@A@g&LPa, & TT+=Ǖ@A@&LPt % &% 3 63  % &% (  & % ( '%  % ( % &% 3 6 _ % &% (  & % ( '%  % ( % &%  _6  % &% (  & % ( '%  % ( % &%  6  % &% (  & % ( '%  % ( % &%  6 k % &% (  & % ( '%  % ( % &%  k63  % &% (  & % ( '% %  %  % ( %  %   TT#Ǖ@A@ LPO?   TT#Ǖ@A@ LPC8   TT#Ǖ@A@ LPH8 % Rpj"Arial|P3'DQ|: (%h|:r|X3'O`:@x:'OLO  4|6'<&P3'h:P3'XX3':X83:<||||:|dv% U Rp"Arial|8|2|||D:2|H:M\: %δMb@2H M MȻ:Hs*#X:b@||||:|dv% U  TT&Ǖ@A@U LP2& % % w % w  TT#Ǖ@A@w LPCV8   TT#Ǖ@A@ LPH8 % %  %   TT&Ǖ@A@ LP3& % % & %  6  % & % (    % ( ' % %  %  % ( %  %   TT`hǕ@A@ LPC8   TTjrǕ@A@ LPH8 % % > % >  TTsxǕ@A@> LP3& % % & %  6  % & % (  >  % ( ' %  % ( % & %  k6 e % & % (  >  % ( ' %  % ( % & %  e6  % & % (  >  % ( ' %  % ( % & %  6 e % & % (  >  % ( ' %  % ( % & %  e6 k % & % (  >  % ( ' %  % ( % & %  k6  % & % (  >  % ( ' %  % ( % & %  6 k % & % (  >  % ( ' %  % ( % & %  6 k % & % (  >  % ( ' % % H %  % ( % H % H  TTǕ@A@H LPO?   TTǕ@A@ LPC8   TTǕ@A@ LPH8 % %  %   TTǕ@A@ LP2& % % $ % $  TTǕ@A@$ LPC8 `  TTǕ@A@` LPH8 % %  %   TTǕ@A@ LP3& % % & % B U6  % & % (    % ( ' % % <%  % ( % <% < TT@RǕ@A@<LP( ] TT@RǕ@A@]LP1`2  TT@RǕ@A@LP) % % H% H% H TTǕ@A@HLP( j TTǕ@A@jLP2E2  TTǕ@A@LP) % F CDIFVjCD0100ChemDraw 8.0.3D  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$2.DkLh@>E 7@\E 7@k^ 7@\&x 7 @>&x  @/^ 7@/9 7@>L #+7f&BLhN:Lhf&BLh#`Br                  2E&KF 7KF 7F` 7Bz 7Bz F` 7 = 7!&8 #+7ff&&ff&#`Br"  #  $  %  &  '  (   ) ! .SP3s_-W@ 7vJ쬰B]jvY kkvJ llvYĻ m+ܨ]쬿U쬰B]쬿#`OHm njkn oklff\PSP3s_#`CH3CH2OH/j3lU 03 7}R÷ȐF^pF^ pq}3c qrh r+!uPuR÷ȐP#`@O-s spqt tqr_323lf#`CH3CH2O;@ 0!  > h߁?:ڋ 7@Xڋ 7Ag4 7BXN 7C:N D+4 7E+}h 7'IL?9sv+}h u+ef/d'dˌ/al# `Ow:&x vx+9s w|:N x } y|vy zvwz {wxff/d'df1߁#`OCH2CH3ON +7ff JJf"z]#`CH3G ?@ H @A I AB J BC K CD L D? M EC P CO T2,xS<UK 7VK 7WF/ 7XBI 7YBI ZxF/ 7[x=c 7\&8} 7YQ 0@:p |+f&RlYRlLht# FCDIF`O?5 }?0 ~@?V     f&Pyك&Pyf<#`OCH2CH3] UV ^ VW _ WX ` XY a YZ b ZU c [Y d \[ =B38D &ChemDraw can't interpret this label.heateQ@3sH@LT@ &ChemDraw can't interpret this label.(1)f3sL &ChemDraw can't interpret this label.(2)*H@H@    +    FDMHCGRTS5}  x (XP`5i   _      o o ""ff):" Q } } n n d5dak5 s sk z          ! OCH2CH3OCH2CH3CH3CH3CH2OCH3CH2OHBr!Br ``  z Lz   `` ^ `` M ``  3 y p `` 7}tv ``  V K V  `` * < <*  (m_pheat  c")")#A(1)   "G "G #_(2)ArialTimes New RomanF MDLSKXY Ariald 0 m68 XIETimes New Romanxheat 0 JXGCTimes New Romanx(1) 0 #XGCTimes New Romanx(2) 0!% ,DD!% ,DfD!% smDD!% 3DfD!% 3DD!% smD@C!% D@C!#Br% _'DD '  '  '  '  '  '  '  '  0!% /DD!% /D D!% PpDD!% ҘD D!% ҘDD!% PpDD!% XLDD!#Br% 0DD '  '  '  '  '  '  '  '  0! CH3CH2OH!% E'f`D!% E':D!O%b 'D'f`D '  ' "4 CH3CH2OH6= E`[D< 0! CH3CH2O!% zED!% >E+D!O% 'DD '  ' "4 CH3CH2O6= EgD< 0!% h0E@D!% h0E@]D!% T@E`D!% @QE@]D!% @QE@D!% T@EC! OCH2CH3!O% +NaEC!% qE?D!% EC! ?QE?D '  '  ' "4 OCH2CH36=  ,NaEC<!%b @QEC '  '  '  '  '  '  '  '  0!% hO-ED!% hO-E0D!% T=ED!% @ME0D!% @MED!% T=ED!% ,^ED! OCH2CH3!O% $fED!% avED!% =OED! UED '  '  ' "4 OCH2CH36=  CnED< '  '  '  '  '  '  '  ' 0 89d2 0 A 89d2 % % VjCD0100ChemDraw 8.0.3D  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$2.DkLh@>E k7@\E l7@k^ m7@\&x n7 @>&x o @/^ p7@/9 w7@>L y#+7f&BLhN:Lhf&BLh#`Br q  r  s  t  u   v   x  z 2E&KF {7KF |7F` }7Bz ~7Bz F` 7 = 7!&8 #+7ff&&ff&#`Br"  #  $  %  &  '  (   ) ! .SP3s_-W@ 7vJ쬰B]jvY &kvJ 'lvYĻ (+ܨ]쬿U쬰B]쬿#`OHm )jkn *klff\PSP3s_#`CH3CH2OH/j3lU 03 7}R÷ȐF^pF^ .q}3c /rh 0+!uPuR÷ȐP#`@O-s 1pqt 2qr_323lf#`CH3CH2O;@ 0!  > h߁?:ڋ 7@Xڋ 7Ag4 7BXN 7C:N D+4 7E+}h 7'IL?9sv+}h =+ef/d'dˌ/al# `Ow:&x >x+9s ?|:N @ } A|vy Bvwz Cwxff/d'df1߁#`OCH2CH3ON +7ff JJf"z]#`CH3G ?@ H @A I AB J BC K CD L D? M EC P CO T2,xS<UK 7VK 7WF/ 7XBI 7YBI ZxF/ 7[x=c 7\&8} 7YQ 0@:p W+f&RlYRlLht `O?5 X?0 Y@?V Z  [ \ ]f&Pyك&Pyf<#`OCH2CH3] UV ^ VW _ WX ` XY a YZ b ZU c [Y d \[ =B38D &ChemDraw can't interpret this label.heateQ@3sH@LT@ &ChemDraw can't interpret this label.(1)f3sL &ChemDraw can't interpret this label.(2)*H@H@    +    Ole EPRINT(* ObjInfo+CONTENTS @     !"#$%&'()*+,0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVWXY]^_`abcdefghijklmnopqrstuvwxyz{|}~,p   uu  KRpTimes New Roman|8|($" 4,|||x%||:|p\"`  |HMx:"X:|||||:|dv%   &% % *v % % * % % * % % ( % s % s RpTimes New Roman @Mx:%:|X: ||||:|dv% s  TTGHNZؕ@-@s LP32 % % % %  TT&-ؕ@-@LP42 % FTECDIFVjCD0100ChemDraw 8.0.3{\{\##C gfL @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`-$$*@@"3@"@( &ChemDraw can't interpret this label. 3+@ 3@  &ChemDraw can't interpret this label. 4(@(@@   )@@   FDMHCGRTSwBY  x (XP`5.'%$.%D%  &%&%3  """#64ArialTimes New RomanF<0MDLSKXY Ariald 0 V  gXC?Times New Romanx3 0 \  XC?Times New Romanx40 i   0 k  % %  VjCD0100ChemDraw 8.0.3{\{\##C gfL @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`/$$*@@"3@"@( &ChemDraw can't interpret this label. 3+@ 3@  &ChemDraw can't interpret this label. 4(@(@@   )@@    VjCD0100ChemDraw 8.0.3h23l_1286446144.!mA. p_'6p_'6Ole -EPRINT-/:ObjInfo0.lm  EMF: ,p  A q KRpTimes New Roman|8|($" 4,|||x%||:|p\"`  |HMx:"X:|||||:|dv%   &%  Y6 S % &% (    % ( '% Rp8"Arial % :|||x%:|# Dht#n#h:n#Xn#x:X:L|||||:|dv%  t%  % ( %  tRp"Arial M MȻ:p3:|X:||||:|dv%  t TT\<eKu@<@ tLPO? % &%  D6 D % &% (   t % ( '% &%  b6 b  t % ( '% (  % ( % &%  S6 M % &% (   t % ( '%  % ( % &%  M6 G  % &% (   t % ( '% % m%  % ( % m% m TTdsu@<@mLPB9 m TTdsu@<@mLPr % &%  M6 M % &% (  m % ( '% %  m%  % ( %  m%  m TT\ddsu@<@ mLPH9 % &%  M6 M % &% (   m % ( '%  % ( % &%  G 6 A  % &% (   m % ( '% % g %  % ( % g % g  TT u@<@g LPH9 g  TT u@<@g LPO? % &%  G 6 G  % &% (  g  % ( '% %  g %  % ( %  g %  g  TT\du@<@ g LPH9 % &%  G 6 G  % &% (   g  % ( '% % a %  % ( % a % a  TTu@<@a LPC9 a  TTu@<@a LPl % &%  A 6 A  % &% (  a  % ( '% %  a %  % ( %  a %  a  TT\du@<@ a LPH9 % &%  A 6 A  % &% (   a  % ( '%  % ( % &%  A 6 ;  % &% (   a  % ( '% % %  % ( % %  TTu@<@LPO? % &%  j63  % &% (   % ( '% &%  T6B   % ( '% ( %  9%  % ( %  9%  9 TTZ cu@<@ 9LPO?  9 TTe mu@<@ 9LPH9 % &%  Y6 $ % &% (   9 % ( '% %  %  % ( %  %   TTu@<@ LPO? % &%  D 6?  % &% (    % ( '% &%  * 60    % ( '% ( %  %  % ( %  %   TTW_u@<@ LPHC9 % &%  ; 6  % &% (    % ( '% %  5 %  % ( %  5 RpTimes New Roman @Mx:%:|X: ||||:|dv%  5  TTAHu@<@ 5 LP1.2 % %  %  %   TT?F.u@<@ LP62 % F CDIFVjCD0100ChemDraw 8.0.3h23lOX gfL @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`($$h23lOX0 %0 &N (+7fJJ dR# `O0 *0 , .#+7e e#`BrN 0+7eJJ232R# `H:0 2 4+7e hh !h#`OHN 6+7e JJ23!2R# `H : 8+7e>71  ?#`Cl :N :+7e>J7J23?2R# `H X0 < >+7h i# `OG<OzM @+7"OIUOIIOX#`OHg B+7ekd li# `Og{J D+7ekFdF23lEN# `H  '  ) +  -  /  1  3  5  7  9   ;   =   ? A  C   E  %@X63N6Z< F&ChemDraw can't interpret this label. 1&@535; G&ChemDraw can't interpret this label. 6F$DMHCGRTS0Ie_  x (XP`5<%&!(*C,q.!02Cr4C!6r8!:<> @BD')+-/135 7 9 ; = ?A C EOBrHOH H Cl H OOHOH `` Eo `` 99 `` 9?j ``  `` j `` M `` Mj `` ^t ta `` R `` mttp `` ms  BF*B1  $Gb$P6ArialTimes New RomanF@3MDLSKXY Ariald 0 !  ] XC?Times New Romanx1 0  N (XC?Times New Romanx6 0!!% O>ED!% O>E E!O% QE E!% O>E_E!% O>E2E!#Br% +E_E!H% QE_E!% O>EDE!O%b +E2E!H% QE2E!Cl% +EDE!H% QEDE!% O>EWE!O% .ED!O%b qlPEY D!O% .E`E!H% NE`E '  ' (  '  '  '  '  '  '  '   '   '   '   '  (  '  '  (  '  % % CONTENTS/ _12864501703!mA. p_'6p_'6Ole ZEPRINT24=OX gfL @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`*$$h23lOX0 %0 &N (+7fJJ dR# `O0 *0 , .#+7e e#`BrN 0+7eJJ232R# `H:0 2 4+7e hh !h#`OHN 6+7e JJ23!2R# `H : 8+7e>71  ?#`Cl :N :+7e>J7J23?2R# `H X0 < >+7h i# `OG<OzM @+7"OIUOIIOX#`OHg B+7ekd li# `Og{J D+7ekFdF23lEN# `H  '  ) +  -  /  1  3  5  7  9   ;   =   ? A  C   E  %@X63N6Z< F&ChemDraw can't interpret this label. 1&@535; G&ChemDraw can't interpret this label. 6 VjCD0100ChemDraw 8.0.3}pnM3sc g&4 @@' :;<   `  3xx# $$$$2      !"#$-()*+,@C/0123456789:;<=>?AB_dEFGHIJKLMNOPQRSTUVWXYZ[\]^`abc|{fghijklmnopqrstuvwxyz}~;D0AtƵD& nmm!2(<.JyZЮƞMC?`\@geAO'0ݯhTwĈaSMIwR?uP+>829:Uz߮4\1OY? ̸TriQJ姨tOD?\<~x%S0?aǭS(CO\8iNmW`*妳'dRŎ]Pb@s(נ)ok^s3D6ڸכ$3>k83ZU-)P,m>R-RɪRk4S@ק@W_`B[O簰Efqw$4?y$'1~R>'/x.Sr>9~ݬg)RƔOsIwOYoEӄo)R)OObå|i>큟I;:&zԛLռK|[1߳oΓ?S5m?mub:7*'Ytt=>^ͼvV"M\Z\w+`ව{ogtL3mKYgT=;Я4PB~j~˵$˓DZ\ᔵ8n-S>}j+bkOת=ذ 69o2Oeⷔ 85?~ L^ z}{X=^g|듨ZM=c UaOCF,wy? ߫eWutu؉^{:uٚ.컻OPہph}(dJjs"pJ:{ u ȥnP00FF&BT%l ۃB 4L79d!mC^:6}6t}mцٶ%#An-rI\F-hǣ!Z LHm g8%݈14n螁 9y(! .d-D/Do3͏yT2 U9Ob퍿3R#WЏQh+ *R!ʅ ʑ9f'+[4hd3`L eIh*N.M!#6I^ fAI.cS"4eeb8#r1M|Cqm㊼jǟJ|ƶߗ+1X*\"[X%˨b9A,gy及BW,t?)JrA\Y.)5bySgbNR4\V,k%˘by_gP,I,:_K]˕ U䪓/S}~ڙ̔ 32)EHXrIH#r$42#==l]\ȓ-q*>Svv^JgFHvlrӔ|aJAM F~KXJ|'_=w:}: 9Xcpq`3 L|r~u}Dܽa3agPB T;QHw'x,ГW\t"Tb1K _w "pD-+hxer>Xm> 氭ڲ5iԏخ-մ¼7%Ʒ<8m^Z`pc5Q2 {qwgx)^F޻ [l [9?\b<x5a` DVN㹅#M=@kxۮ T= ی )1eTY>L؄evKI9g JEFժJ  *7VPѴ;^8JCyf0!)jh.{N! 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