ࡱ>  "a:{Z'` bjbj{P{P 2,::c8, D\b ,!"N!N!N!%%%y/{/{/{/=/E[$]hA`Z[&%%&&[N!N!S[|*|*|*&ZN!N!y/|*&y/|*|*Y--N!V һ'q--/L[0\y-,`(6`-`-%0%"|*%&%%%[[*^%%%\&&&& 1. Nomenclature Give the proper systematic name for each of the following structures on the lines.  EMBED ChemDraw.Document.6.0  2. Concepts Label each of the following compounds as AROMATIC, NONAROMATIC or ANTIAROMATIC on the lines provided.  EMBED ChemDraw.Document.6.0  3. Reactions Draw the major product or products of each of reaction in the boxes provided. If multiple organic products are equally likely, show each. For stereoselective reactions, be certain that your structures clearly indicate stereochemistry.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  4. Mechanisms Draw a complete arrow pushing mechanism for the following reaction. Include all resonance forms for your intermediates. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  5. Synthesis Propose a selective multi-step synthesis of each target molecule starting with the compound provided. Show the necessary reagents and products for each step. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  6. Application of Concepts a. The following hydrocarbon is actually a polar compound. Why is it polar, and which direction is the dipole oriented? Thoroughly explain your rationale (structures will be helpful).  EMBED ChemDraw.Document.6.0  b. Rank the following hydrocarbons in order of increasing acidity (1 most acidic to 3 least acidic). Thoroughly explain your rationale (structures will be helpful).  EMBED ChemDraw.Document.6.0      CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 3 PAGE  PAGE 1 cd   ! 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JzF 2LV$  "L ]            !!%&#$"#$%&""''()*).*++,,--.01/012233/0467567889956:9;?@=><=>?@<=AAB N NNO)NH+NH-NH/S1N5O<NH `` OU- `` NPKT `` 5; `` ('( `` -  `` QK `` 510U ``  Gx `` y!2!-! `` 3. `` [>9a^Times New Roman@@FMDLSK XY Times New Romand 0!N%b * LEmE !% VAEKD !% +6EzE !% `:ER E !% GEJ E !% @ED !% NE]D  '(. '(. ' ' ' ' '(. 0!O% p^ODD !% *`DE !% D6 E !% k.DAiD !% ֆzDD !% DDE !% zDD  '(. ' ' '(. ' ' ' 0 !S% zEPD !% 4~EqE !N% ՅELaE !% OEnD !% eEmD !% .PwE E  '(. ' ' '(. ' ' 0 !N%b DjCE !% D=[QE !N%b uD#"XE !% g EmyQE !N%b ECE !% E~=E  ' ' ' ' ' ' 0!% -E>SE !% 4E>8[E !% `EMSE !% BEFpFE !% ,ۢEfFE !% a1EέVE !% aEME  '(. '(. ' ' ' ' '(. 0 !% NEpD !% 1LEE !O% &E E !% wEE !% zEeD !% "E`D  '(. ' '(. ' '(. ' 0 !% .AD@AE !% [QDLHE !% 9OQD VE !% tD\E !% aDVE !% lDHE  '(. '(. ' '(. ' 0 !% (DD !% DrE !N% ׻D,<E !% = EE !%  E D !% oDeD  '(. ' '(. ' '(. ' 0 !N% 7E{HE !% q=ESE !N% DEHE !% 2EZE !% IEZE !% 1UESE  ' ' '(. ' ' ' 0!% hEGE !% ehENUE !% }YtE[E !% ttE+@E !% 1 EGE !% E%UE !% 3хE[E !% #E7 0 E % % ( ObjInfo CONTENTS_1327483585'!mA. һһOle VjCD0100ChemDraw 8.0;_a5pwXa1 gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`&8$$9&+s-#^Q:&8|vF +78\C8BQ#`NH;&<4 <&Xy# 7=&J4* 7>&y~? 7?&K74 7@&iI 7A& =&>& D&E&B& ;&<& C&F&D&C& :&;& D& <&=& E& >&:& F& ;&?& G& ?&@&H&;_lN p vI&YR +7YZOYֿOƍV# `OJ&+Y K&6o 7L&gu 7M&5d N&3mN 7O&_ d 7P& J&K& Q&U&R&Q& I&J& R& K&L& S& L&M& R&V&T&T& M&I& U& J&N& V& M&O& W&(|DX&} +7}E}ƶ㬾oҒ# `SY&4 Z&F +7".5# `N[&wͲ 7\&D 7]&W| 7^& Y&Z& _&c&`&_& X&Y& `& Z&[& a& [&\& `&b&b& \&X& c& Y&]& d&YI.x}ee&CZ96K +7C:=6Cz5x=6#`NHf&bNC/ 7g&8Y +78]c8U#}eĖ#`NHh&(O? 7i&92 +7j=2J52 \=#`NHj&.y 7k& e&f& l& e&j& m& f&g& n& g&h& o& h&i& p& i&j& q&n0==!_*%r&Qf s&c^ 7t&IRed% 7u&p= 7v&q=#  7w&}|Wj 7x&H 7y& u&v& |&}&z& s&t& {&|&{& r&s& |& t&u& }& v&r& ~& r&w& & w&x&&t>ET&6 7& 7&PǮ +!7PPI# `O&t 7&ba 7&e 7& && U&& && & && &&& && T && &UU && &`` *&!  &6Sacy&4M6f 7&@S 7&wVJS 7&Y\aTf 7&1Vmy 7&AH#y 7& &&^ &&& && & && &&& && &ɹ-ZY5cC 7dUQ 7e-/ +7 MߓY# `Nfe~ 7g 7hQ[ 7i cd &&& de & ef &&& fg & gh &&& hc &S.<(H^=U&+@$ +7+C~!+?<>!KD(# `N&R/ rS@Y: +7SCY77S.<Y6;Dj># `N&] 7&]pB 7&RpU 7& && w r& x &r &wy  && z  && {  && |e4t,`7}7[?;t  7~IT`t  7_ 7E4A! 7s?6 7> U雙 7s_ 7 7%-U 7Ɓ?; 74X 7 }~  ~      }           rt6r;   rWr ! r9ra " k/ # @/ $ v*vc7v*v % v*vsv*v & v*vӄv*va ' jFvljFvo ( jFvjFvR 0 ) EPRINTdObjInfoCONTENTS(!_13274836016!mA. һһ      !"#$%&')*+,-./012345678<=>?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~l1xD EMFd @  z   KRp8Times New Roman| : H@B|r|B|| 4Pt<X< ||||<|dv%   &% % +( H% % +( wHK% % +(  HR% % +( H % % +( H% % % V0~uuju% % % ( u6Qu% % V,wPwPss% %  % %  P &% '%  % ( &% ( % % V0<?XbXLX% % % ( W6eW% % V,=>ZdZdVV% %  % %  P &% '%  % ( &% ( % % V0ad   t  % % % (  6W % % V,bc V V~ ~ % %  % %  P &% '%  % ( &% ( % % V0% % % ( 6d% % V,cc% %  % %  P &% '%  % ( &% ( % % V0     % % % (  6X % % V, W W  % %  % %  P &% '%  % ( &% (  6h  % &% (  P &% ( '%  6X  P &% ( '% (  % ( &% ( h 6+  % &% (  P &% ( '%  % ( &% ( + 6h  % &% (  P &% ( '% + 6X  P &% ( '% (  % ( &% ( h 6  % &% (  P &% ( '%  % ( &% (  6+Z  % &% (  P &% ( '%  6+y  P &% ( '% (  % ( &% ( +Z 6  % &% (  P &% ( '% % ( % Iz %  % ( % Iz RpTimes New Roman @4P< <|X<  ||||<|dv% Iz  TTah@@Iz LPB2 z  TTjm@@z LPr % &%  6Ek  % &% (  z  % ( '% % G %  % ( % G % G  TT` i@@G LPN8   TTj r@@ LPO8 % RpjTimes New Roman|hQrHQ f?b@i@|P@[? f@c [D4P<hX<DT ||||<|dv%  RpTimes New Roman |(|"|||D<"|H<Ppj<ؓ Pb@H  4P<X<b@ ||||<|dv%   TTtx@@ LP2 % % &% h 6;  % &% (    % ( '% %  %  % ( %  %   TT@@ LPC2   TT@@ LPH8 % %   %    TT@@  LP3 % % ? % ?  TT@@? LPO8 % % { % {  TT@@{ LP- % % &% 6M % &% (  {  % ( '% &% 6= {  % ( '% (  % ( % &% M6+ % &% (  {  % ( '%  % ( % &% +6M % &% (  {  % ( '% &% +6= {  % ( '% (  % ( % &% M6 % &% (  {  % ( '%  % ( % &% 6+? % &% (  {  % ( '% &% 6+^ {  % ( '% (  % ( % &% +?6 % &% (  {  % ( '% % I_%  % ( % I_% I_ TTah@@I_LPB2 _ TTjm@@_LPr % &% 6EP % &% (  _ % ( '% % G%  % ( % G% G TT`i@@GLPN8  TTjr@@LPO8 % % %  TTtx@@LP2 % % &% M6; % &% (   % ( '% % %  % ( % %  TT@@LPN8  TT@@LPa&  TT@@LPN8 B TT@@BLPH8 % % ~% ~ TT@@~LP2 % % % F% F% F TT@@FLPN8 F TT@@FLPH8 % % X% X TT@@XLP3 % % F% F TT@@FLP  3F TT@@3FLP( OF TT@@OFLPl fF TT@@fFLPi }F TT@@}FLPq, F TT@@FLP) % &% % 6  % &% (  F % ( '% &% 4 6  F % ( '% (  % ( % &%  6+3  % &% (  F % ( '%  % ( % &% +3 6  % &% (  F % ( '% &% + 6  F % ( '% (  % ( % &%  6%  % &% (  F % ( '%  % ( % &% % 6+ % &% (  F % ( '% &% 4 6+ F % ( '% (  % ( % &% +6%  % &% (  F % ( '% % G%  % ( % G% G TTa?hM@@GLPC2  TTi?qM@@LPH8 % % %  TTsDwO@@LP3 % % &% % 6B % &% (   % ( '% % GS %  % ( % GS % GS  TT`xi@@GS LPN8 S  TTjxr@@S LPH8 % % f % f  TTt}x@@f LP2 % % &%  6;  % &% (  f  % ( '% % Na %  % ( % Na % Na  TTR`@@Na LPN8 a  TTR`@@a LPa& a  TTR`@@a LPN8 a  TTR`@@a LPO8 % % 't % 't  TTWb@@'t LP2 % % Fa % Fa  TTR`@@Fa LP, [a  TTR`@@[a LP  pa  TTR`@@pa LPH8 a  TTR`@@a LPC2 a  TTR`@@a LPl % % % %  %  %   TTgu@@ LP0&   TTgu@@ LP  % % % %  %   TTdo@@ LPo % % % 6 % 6  TTgu@@6 LPC2 % &% ,6 % &% (  6  % ( '% &% <6 6  % ( '% (  % ( % &% 6: % &% (  6  % ( '%  % ( % &% :6 % &% (  6  % ( '% &% 6 6  % ( '% (  % ( % &% 6, % &% (  6  % ( '%  % ( % &% ,6 % &% (  6  % ( '% &% <6 6  % ( '% (  % ( % &% 6, % &% (  6  % ( '% RpTTimes New Roman|x<:Bآآ| r|B x<|BA|| ,Lh<Xx<X< \ ||||<|dv% %  % ( % RpTimes New RomanM/M'Y@y +!#&}cr=J&}#`@O-E'q=  F' E'B'G' B'C'H' B'D'׃sZâsـ#`NO2I' 9':' N'J'J' :';' K' ;'<' J'P'L'L' <'=' M' ='>' L'O'N'N' >'9' O' ='?' P' <'@' Q' 3? 3KR'?ʅ3C 7(Iqm"0kT'V#qm U'V#  +!  I "0k#`@O-V' T'U'?3 3? 3K#`CH3O-W'9WN͌׀X'g N 7Y' N 7Z'LLa 7['t \'gt ]'La 7^'q #+7q9qVfFq#`Br_'Lq 7(8mN:a'94x7 +!xZx949#`@N+b'x7 +xO8xOkD# `Oc't +!ljxl'm jx#`@O-d'>  e' d'a'f' a'b'g' a'c',qZlq͌׀#`NO2h' X'Y' m'i'i' Y'Z' j' Z'[' i'o'k'k' ['\' l' \']' k'n'm'm' ]'X' n' \'^' o' ['_' p'>3>q'>3 7(ף3qs'>3  +p3Sף3q3S#`Nat'> +p̈́ף̈́q#`NH2u' s't'>j3'>3>#`NaNH2v'\/ WN\?׀w') N 7x'u. N 7y'B9La 7z'u.F CDIFt {')t |'\La 7}'\q +7\qn\/ q.\O #`CH3~'B9q +7"=qZb5q\?׀#`NH2' w'x' ''' x'y' ' y'z' '''' z'{' ' {'|' '''' |'w' ' {'}' ' z'~' '=j3g=j"f'=J3 7((=J+(=J3 +(((=* 3=j3g=j"f#`NaNO2, HCl'JX,<DW'&Y '\i&Y 7'*6k 7'\i~ 7'~ 'k 7'x6 7("iwS'(T7 '(!Ħ +_J[y# `N'({  ' ''' ''\dJX$DW#`CN'`cF +7\zIJX,<,I#`OH' '' '''' '' ' '' ''' '' ' '' '''' '' ' '' ' '' 'w׽C'w 7((u+!(OC<+!(IC<+(+(((((((((((Q+(+(L+(`+(QO+((((((((((((ww׽C#`HNO3, H2SO4d(%2"Ga]e('@ G 7f(6VfcG 7g(xpaZ 7h(XVl 7i( Al j(E6+Z 7k(6r 7(6|h Ei'm(6r n(@i' o(@ܽl  p( o(m(q( m(n(9*|%2{E<]#`CH2CH3r( e(f( w(s(s( f(g( t( g(h( s(u(u( h(i( v( i(j( u(x(w(w( j(e( x( i(k( '3{3;ofn &ChemDraw can't interpret this label.`NH3 (liq)'p03Sq&3q29 &ChemDraw can't interpret this label.$@0 oC(gDg<|gFt"  p ````````` `Cl2, FeCl3'ms)    'j)    'Y)Wsa    'E.M)G    'FCDIF)$)    '0o'0;    'G{G~    '#"#    '[v_[vs    '֌"֌     (( d( W' '( W' v' ' p'( v' 8' ' '( 8' ' ' Q'( ' ' 'FzDMHCGRTSz x9 `* "OC*"O *"g"O*"O=**"O$'C' q P AoA R = 8 &!&()Xl( & %l% X%5d##y   y 6 n##  n    sE|# ,#! , |  !         !#$$%%&&''((#')&*CH2CH3 HNO3, H2SO4CNOH NaNO2, HClCH3NH2NaNH2 Br!NO2"CH3O-)Br*NO2 ``    s `` '.&']] ``&; % &>  ``&;%&> `` !& `` f D ?  ``  C+ >  ``   U"G ``  G H B  `` C C >s  `` % ``  GW B  `` !R C >!  ``  r; NH3 (liq)  @@  n i0 oC f `` `` `` `` `` `` `` `` ``  `` ^  Cl2, FeCl3Times New Roman@@F MDLSK XY Times New Romand 0 9P XSO Times New Roman dNH3 (liq) 0 4  XTimes New RomandTimes New RomandTimes New Romand0 oC 0 au X Times New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dTimes New Roman dCl2, FeCl3  0!% P|DDgsE !% P|DD3E !% <@sD3E !% D3E !% DgsE !% <@sDg&mE !#Br% dDg&mE !NO2!N% "D3sE !O% "D3E !O% )D3ӊE ! RD3ӊE  ' '( '"4NO26=  dD3E < '(. ' '(. ' '(. ' ' ' 0!CH3O-!% gdEuE !O% f EuE  '"4CH3O-6= *EgsE < 0!% P|DDD !% P|DDD !% <@sD`D !% DD !% DD !% <@sD`D !#Br% dD`D !NO2!N% VD`E !O% VDGD !O% ^D E ! NgD E  ' '( '"4NO26=  dD`D < '(. ' '(. ' '(. ' ' ' 0!NaNH2! Na% E,D !N%b 2E,D  '"4NaNH26= E,D < 0!% P|DD/E !% P|DD =E !% <@sDCE !% D =E !% D/E !% <@sD(E !%b dD(E !N%b dDCE  '(. ' '(. ' '(. ' ' ' 0;0 !1 0!Cl% EyD ! Na% ѨEyD  ' 0! DDf1E  0!% _^D@E !% _^DE !% $D`E !% "DE !% "D@E !% $DE !CN!% )DE !N% )uDE ! )DE  ' '("4CN6=  DE <!O%b p/DE  '(. ' '(. ' '(. ' ' ' 0;0 !B1 0!N% մEOFD !O% EħD !O% E6tD !O% EOFD  ' '(. ' 0 !S% EeD !O% EuD !O% ЕEݽD !O% zEݽD !O% EeD  '(. 'FMDLSK ' ' 0! UDE  0!% 2Dd"D !% x2DhXD !% 7aD,sD !% }D\XD !% D"D !% maDjD ! CH2CH3!% JODD !% CD"D ! SD"D  ' '"4 CH2CH36=  JODD <  '(. ' '(. ' '(. ' '0 !' 0 _' 0 '3 0 '  0 'm 0 `89d20 w89d20 f gf 89d20 v 89d20 h89d2% % VjCD0100ChemDraw 8.09,<5F& gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`(8$$8'wWNـ9'q= N 7:' כ N 7;'ףLa 7<' כt ='q=t >'p{La 7?'p{s #+7PswsVqs#`Br@'ףs 7(rCB'pN +! WN[ N[p#`@N+C' כN +qN N ؏# `OD'q=>y +!#&}cr=J&}#`@O-E'q=  F' E'B'G' B'C'H' B'D'׃sZâsـ#`NO2I' 9':' N'J'J' :';' K' ;'<' J'P'L'L' <'=' M' ='>' L'O'N'N' >'9' O' ='?' P' <'@' Q' 3? 3KR'?ʅ3C 7(Iqm"0kT'V#qm U'V#  +!  I "0k#`@O-V' T'U'?3 3? 3K#`CH3O-W'9WN͌׀X'g N 7Y' N 7Z'LLa 7['t \'gt ]'La 7^'q #+7q9qVfFq#`Br_'Lq 7(8mN:a'94x7 +!xZx949#`@N+b'x7 +xO8xOkD# `Oc't +!ljxl'm jx#`@O-d'>  e' d'a'f' a'b'g' a'c',qZlq͌׀#`NO2h' X'Y' m'i'i' Y'Z' j' Z'[' i'o'k'k' ['\' l' \']' k'n'm'm' ]'X' n' \'^' o' ['_' p'>3>q'>3 7(ף3qs'>3  +p3Sף3q3S#`Nat'> +p̈́ף̈́q#`NH2u' s't'>j3'>3>#`NaNH2v'\/ WN\?׀w') N 7x'u. N 7y'B9La 7z'u.t {')t |'\La 7}'\q +7\qn\/ q.\O #`CH3~'B9q +7"=qZb5q\?׀#`NH2' w'x' ''' x'y' ' y'z' '''' z'{' ' {'|' '''' |'w' ' {'}' ' z'~' '=j3g=j"f'=J3 7((=J+(=J3 +(((=* 3=j3g=j"f#`NaNO2, HCl'JX,<DW'&Y '\i&Y 7'*6k 7'\i~ 7'~ 'k 7'x6 7("iwS'(T7 '(!Ħ +_J[y# `N'({  ' ''' ''\dJX$DW#`CN'`cF +7\zIJX,<,I#`OH' '' '''' '' ' '' ''' '' ' '' '''' '' ' '' ' '' 'w׽C'w 7((u+!(OC<+!(IC<+(+(((((((((((Q+(+(L+(`+(QO+((((((((((((ww׽C#`HNO3, H2SO4d(%2"Ga]e('@ G 7f(6VfcG 7g(xpaZ 7h(XVl 7i( Al j(E6+Z 7k(6r 7(6|h Ei'm(6r n(@i' o(@ܽl  p( o(m(q( m(n(9*|%2{E<]#`CH2CH3r( e(f( w(s(s( f(g( t( g(h( s(u(u( h(i( v( i(j( u(x(w(w( j(e( x( i(k( '3{3;ofn &ChemDraw can't interpret this label.`NH3 (liq)'p03Sq&3q29 &ChemDraw can't interpret this label.$@0 oC(gDg<|gFt"  p ````````` `Cl2, FeCl3'ms)    'j)    'Y)Wsa    'E.M)G    ')$)    '0o'0;    'G{G~    '#"#    '[v_[vs    '֌"֌     (( d( W' '( W' v' ' p'( v' 8' ' '( 8' ' ' Q'( ' ' 'Ole EPRINT;ObjInfoCONTENTSF|l|2xD EMF @     oKRp8Times New Roman| : H@B|r|B|| 4Pt<X< ||||<|dv%   &% % + % % +g% % + o% % + % % +!% 6a % &% (  k  &% ( '% 6R k  &% ( '% (  % ( &% ( a6 % &% (  k  &% ( '%  % ( &% ( 6c % &% (  k  &% ( '% 6S k  &% ( '% (  % ( &% ( c6 % &% (  k  &% ( '%  % ( &% ( 6T % &% (  k  &% ( '% 6s k  &% ( '% (  % ( &% ( T6 % &% (  k  &% ( '%  % ( &% ( 6UR % &% (  k  &% ( '%  % ( &% ( UR6 % &% (  k  &% ( '%  % ( &% ( 76 % &% (  k  &% ( '% 1G61 k  &% ( '% (  % ( &% ( 6F % &% (  k  &% ( '%  % ( &% ( F6M % &% (  k  &% ( '% '62 k  &% ( '% (  % ( &% ( M6M8 % &% (  k  &% ( '%  % ( &% ( M86 % &% (  k  &% ( '% 2G6 k  &% ( '% (  % ( &% ( 67 % &% (  k  &% ( '%  % ( &% ( M86 % &% (  k  &% ( '%  % ( &% ( `6 % &% (  k  &% ( '% p6 k  &% ( '% (  % ( &% ( 6o % &% (  k  &% ( '%  % ( &% ( o6+ % &% (  k  &% ( '% O6 k  &% ( '% (  % ( &% ( +6+a % &% (  k  &% ( '%  % ( &% ( +a6 % &% (  k  &% ( '% p6& k  &% ( '% (  % ( &% ( 6` % &% (  k  &% ( '%  % ( &% ( % % V0~"Z_Z% % % ( ]6% % V,__% %  % %  k  &% '%  % ( &% ( % % V0<%?tnstnit% % % ( qt6 t% % V,=>sv v rsr% %  % %  k  &% '%  % ( &% ( % % V0a#d ` e `  % % % ( c 6 % % V,bce   e % %  % %  k  &% '%  % ( &% ( % % V0% mr m % % % ( p 6  % % V,r   r % %  % %  k  &% '%  % ( &% ( % % V0# a f a  % % % ( d 6 % % V,f   f % %  % %  k  &% '% % ( % %  % ( % RpTimes New Roman @4P< <|X<  ||||<|dv%  TT@@LPH8 % RpjTimes New Roman|hQrHQ f?b@i@|P@[? f@c [D4P<hX<DT ||||<|dv% :RpTimes New Roman |(|"|||D<"|H<Ppj<ؓ Pb@H  4P<X<b@ ||||<|dv% : TT@@:LP2 % % Y% Y TT@@YLPN8  TT@@LPN\8  TT@@LPH38 % %  %   TT@@ LP20 % % -% - TT@@-LP,\ A TT@@ALP R V TT@@VLPHX8  TT@@LPOH8 % % %  TT@@LP-\ % % &% , 6,  % &% (   % ( '% &% G 6G   % ( '% (  % ( % &% , 6  % &% (   % ( '%  % ( % &%  6H  % &% (   % ( '% &%  6-   % ( '% (  % ( % &% H 6H  % &% (   % ( '%  % ( % &% H 6  % &% (   % ( '% &% - 6   % ( '% (  % ( % &%  6,  % &% (   % ( '%  % ( % &% H 6  % &% (   % ( '% %  %  % ( %  %   TT@@ LP2&   TT@@ LP-   TT@@ LPb, !  TT@@! LPu, J  TT@@J LPt b  TT@@b LPa&   TT@@ LPn,   TT@@ LPo,   TT@@ LPl   TT@@ LP,   TT@@ LP    TT@@ LPH8 % % W % W  TT@@W LP2 % % v % v  TT@@v LPS,   TT@@ LPO8 % %  %   TT @@ LP4 % % &% 67 % &% (    % ( '% RpTTimes New Roman|x<:Bآآ| r|B x<|BA|| ,Lh<Xx<X< \ ||||<|dv% #%  % ( % #RpTimes New RomanM/M'Y@ +7;;WQH#`OH(  ( ( (((  ( ( (  ( ( (((  ( ( (  (( (((( ( ( (  (( (~1Y yS(  7(W  7(c/ǥ 7(W۱/ 7(۱/ (Ёǥ 7(Ё@ 7(ɝrS 7 ( (( %(!(!( (( "( (( !(#(#( (( $( (( #(&(%(%( (( &( (( '( (( ((Rj=RGU)(RJA 7((uRWZʹ+(RJAu~[  +Du,]t=uRDul]#`Na,(RJAB q  +D'nt=mDgx#`Na-(IPa +SlLlOITlO#`Cr.(RJA$ +D$=RD#`Cr/(V$ +0Z t,S͘WZ@# `O0(IP +SЉLIT# `O1(RJA +DF CDIFڀ=@RD# `O2(Z 2 +f5Љb.Z5# `O3(+$ +/ (͘=/@# `O4(Z 2a +f5Jb. Z5}# `O5(RJA +Dt=tZRDʹ# `O6( +(,(7( -(.(8( .(/(9( .(0(:( .(1(;( .(2(<( .(3(=( .(4(>( .(5(R*E<Rj=RGU#`Na2Cr2O7?(ӂ,B@(fΚ + 7—ӂ,B/An atom in this label has an invalid valence.# DA(a&eZB(aAh 7aea&eZ&ChemDraw can't interpret this label.#$phenyldiazonium chloride(e1 =]Q(;Y 7(2Y 7(x<e( 7(2q9 7(;q9 (de( (޴e( (DY 7(Dq9 7(d}J #+7D]GGݐ]Q#`Br( (( ((( (( ( (( ((( (( ( (( ((((( (( ( (( ( (( ( (( ( (( D((aO(B. `H2NNH2, HO-E()y)-y)- 5This label has conflicting or unassignable charges.`2-butanol, H2SO4F( UH~`M~Wl `H2SO4, H2O(>!>Ç>$샲 `Br2, FeBr3G(mbu#w{    H(#w    I(ٹwWb    J(ENw    K()&w    L(0ˀ08c    M(zImzIe    N(V%~0V%Dd    O([o[e    P(V~LV`d     (( ' ' M( ((( ' ( O( ?(( ( ( N(( ( ( P(( ( L( A(F8*DMHCGRTS x9 `* +EVa9*EV 9*"EV9*%EV[9**EV$.9'8J'/8x/8W/_8v_/8Y/p))+',|p,|+'"+'])],|-&0%42) r)!7*d r++$*d$-.'&((())(+s''+t&P)&O,*((*N+,+T*QO-:'. x'{)'x(,*d z*d ( + v-O&-O .     !! ""#$%%&&''(())$(**++,+- Br phenyldiazonium chloride D Na2Cr2O7OH,O `` -^-.[  'I/&/'u8$  N33{4] `` g2@2;5b ``&,&,&- ``i-- l- ``  2; N26=6 H2NNH2, HO- `` 1?1~7 2-butanol, H2SO4 `` 1 15 H2SO4, H2O `` 225 Br2, FeBr3Times New RomanSymbol@@FMDLSKXY Times New Romand 0 cXWS Times New Roman dH2NNH2, HO- 0 Xa]Times New Roman d2-butanol, H2SO4 0 kXUQ Times New Roman dH2SO4, H2O 0 M h XUQ Times New Roman dBr2, FeBr3 0!% E9D !% E D !% EE !% EvD !% xED !% @E3D !% `gE*D !% c?ElD !O% c?ElD !% ED  '(. ' '(. ' '(. ' ' ' '( '  0!% 4rE-U%D !% gEX[D !% 8ExvD !% E[D !% E%D !% EE D !% E D !% PĺE$D  '(. ' '(. ' '(. ' ' ' 0!% *E4E !% EXE !% yEE !% ͭEfE !% ]ЭEE !% $EdAE !O%b ۨE?E  '(. ' '(. ' '(. ' ' 0!% @E^IwE !% @EoˁE !% ΓEބE !% EoˁE !% E^IwE !% ΓE"qE !% Z;E"qE !% EwE  '(. ' '(. ' '(. ' ' ' 0! Na2Cr2O7! Na% E9#D ! Na% SE9#D !Cr% E6RID !Cr% E9#D !O% EYD !O% wE6RID !O% E9#D !O% wEBC !O% EC !O% EBC !O% E9#D  ' ' '( '( '( '( '( ' ( ' ("4 Na2Cr2O76= E9#D < 0!H% `ED  0!phenyldiazonium chloride |EE  0!% LEK3E !% LE?E !% ΟEEE !% E?E !% EK3E !% ΟE^-E !% ΟE !E !% LEJE !% EJE !#Br% ZGE^-E  '(. ' '(. ' '(. ' ' ' ' ' 0 0" 0 n" 0  "B 0  "  0 "| 0 %89d20 <89d20 +u u 89d20 ;//89d20 ,89d2% % VjCD0100ChemDraw 8.0˹5'/Ey gfg& @@3 :;<   `  QzG"x# $$$$8 @@%Times New RomanSymbolxXX$dg(XX$dd'`(8$$'8b8V'r9_ 7' ; 7'A  7':› 7'{ '1á  7'UJ1 7'V C '} C +7J@Eצ@}p G# `O'ѲV 7' '' ''' '' ' '' ''' '' ' '' '''' '' ' '' ' '' ' ''' '' '6 bU'"B   7'!Wf  7'cb 7'CWC0 7'9BL0 'r7ԫ 7'27B 7'AhU 7' '' ''' '' ' '' ''' '' ' '' '''' '' ' '' ' '' (z QH (? 7 (L ; 7 (g 7 (n l+, 7 (#2]4, (j 7(We#> +7;;WQH#`OH(  ( ( (((  ( ( (  ( ( (((  ( ( (  (( (((( ( ( (  (( (~1Y yS(  7(W  7(c/ǥ 7(W۱/ 7(۱/ (Ёǥ 7(Ё@ 7(ɝrS 7 ( (( %(!(!( (( "( (( !(#(#( (( $( (( #(&(%(%( (( &( (( '( (( ((Rj=RGU)(RJA 7((uRWZʹ+(RJAu~[  +Du,]t=uRDul]#`Na,(RJAB q  +D'nt=mDgx#`Na-(IPa +SlLlOITlO#`Cr.(RJA$ +D$=RD#`Cr/(V$ +0Z t,S͘WZ@# `O0(IP +SЉLIT# `O1(RJA +Dڀ=@RD# `O2(Z 2 +f5Љb.Z5# `O3(+$ +/ (͘=/@# `O4(Z 2a +f5Jb. 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' '(. ' '(. ' ' ' '( 0!CuCN!Cu% !E3CE !% rE3CE !N% E3CE  ' '("4CuCN6= rE3CE < 0!Cl% UDE  0!% `[DF !% ?ZD/xF !% zD:+F !% D<F !% "DF !% (لDlF !% DkF !% DF !% GDkF !O% D{F  '(. ' '(. ' '(. ' ' ' ' ' ( 0!% .YDŭE !% XD9nE !% QDNE !% "DT|E !% -D=E !% DVE !% }DCE !O%b DE !O% }DE  '(. ' '(. ' '(. ' ' ' '( 0!% 0;DF !% D* F !% zRD5 F !% ƯD8 F !% үDF !% (DF !#Br% aD1F  '(. ' '(. ' '(. ' ' 0!% 5~DS.F !% |~DO1F !% 䁖DYf3F !% GD\1F !% tDV.F !% D,F !O% DVD)F FxjMDLSK!% D'F !O% έD,$F !% QD?)F  '(. ' '(. ' '(. ' ' ' '( '  0!Cl% EJ*F !% yE<)F !% ) E*F !O% OhE%F  ' ' '(0 Y% 0 % 0 %%j( 0 %;$ 0 ?)%, 0 *]*89d20 u89d20 "d"89d20 WtW89d20 &e&89d2% % CONTENTSG\_1327481079!mA. һһOle  EPRINT V|GVjCD0100ChemDraw 8.0mzVs|/E gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`(8$$'RXeQ>g' e 7' e 7'kx 7'A 'A 'R8x 7'R8q #+7Rq֚RXqeq֤#`Br'kq +!7KqqZQ͡# `N'k +7K 4 Q>g# `N' '' ''' '' ' '' '''' '' ' '' '''' '' ' '' ' '' ' '' 'MVMV+ '!  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' '(. ' '(. ' ' ' 0!% aE3E !% =E~AE !% ȄEWJHE !% taEߚAE !% ?dE 4E !% rEQ-E !O% EP E !%b $`EE !SO3H !S% wEUE !O% 3EUE !O% wEIcE !O%b EUE ! wEYHE  ' '( '( '"4SO3H6=  wEUE < '(. ' '(. ' '(. ' ' ' '0   89d2% % ObjInfo! CONTENTS _1327481109 $!mA. һһOle >@@Times New RomanxXX$dg(XX$dd'`&8$$&@UAt& i&A 17&aw6A 27&VAS 37&6?`f 47& /if 57&G/S 6&܁+S 7+7a+Pܡ+OB^EW# `O& \f 8+7s c bt#`CH3& 9&& &&& :&& & ;&& &&& <&& & =&& &&&& >&& & ?&& & @&& &363+\\)& A7&z5s B7&v@M C&5r D7& b E7&aO; F& G+7`f3 # `O&3@ H+73@3@E3)#`CH3&+Vd I7&XN<1H]od !&+Vd ++Yd'+7&@)c ?& v @7&@\ A7&\ BLڄv C7Lڄ{ J7&LZk +&Lڄ{ 6+!{y{yLڈ#`@N+&@o{ 7+'s{)LZk{)MsG# `O&AƮ 8+!}Aު}͉Aު㳓 +#`@O-&\ 9 & :&&& ;&&& <&&L{L{uL۪#`NO2@I M +7 dG`$GmL# `F& D&& && E&& & F&& &&& G&& & H& & I&  K&  N& L( Q L+!7hL( Q#`HO- 3B+[f4ֻKP V7pUKP W="tc X7pU:u Y7ֻ:u Z tc [7 j b7& ok4tq  j O+!oՈ҄o҄ k#`@N+pUoj P+;s okd >= :EV EW X 2Y :2Z b[ bb>d  L 9> ? E@ A 9 B a EC a 1JM\]^_`ace D E F G H I K NNO2OHHO-NO2F ``  e `  `` d ag ``   E 0 ``   Y `` b hTimes New Roman@@FMDLSKXY Times New Romand 0!% yDߐD !% yDD !% QDD !% ⳫDD !% ⳫDߐD !% QDD !NO2!N% DD !O% DD !O% wDݐD ! ⳫDސD  ' '( '"4NO26=  DD <! F% 48DPD  '(. ' '(. ' '(. ' ' ' 0!O%b `ED  0!% M/RE̪D !% M/RE̪D !% H]E*D !% DiE̪D !% DiE̪D !% H]E*D !NO2!N% @BuE*D !O% @BuE*D !O% yEʪD ! DiE̪D  ' '( '"4NO26=  @BuE*D <!O%b `AEjD  '(. ' '(. ' '(. ' ' '0 89d2% ( % VjCD0100ChemDraw 8.0L$Gmf4 gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`&8$$&L$Gm۪&)c >7&@)c ?& v @7&@\ A7&\ BLڄv C7Lڄ{ J7&LZk +&Lڄ{ 6+!{y{yLڈ#`@N+&@o{ 7+'s{)LZk{)MsG# `O&AƮ 8+!}Aު}͉Aު㳓 +#`@O-&\ 9 & :&&& ;&&& <&&L{L{uL۪#`NO2@I M +7 dG`$GmL# `F& D&& && E&& & F&& &&& G&& & H& & I&  K&  N& L( Q L+!7hL( Q#`HO- 3B+[f4ֻKP V7pUKP W="tc X7pU:u Y7ֻ:u Z tc [7 j b7& ok4tq  j O+!oՈ҄o҄ k#`@N+pUoj P+;s ok 6=  % &% (   % ( '% &% Y 6X   % ( '% (  % ( % &% = 6  % &% (   % ( '%  % ( % &%  6u  % &% (   % ( '% &%  6Z   % ( '% (  % ( % &% u 6u  % &% (   % ( '%  % ( % &% u 6  % &% (   % ( '% &% Z 6   % ( '% (  % ( % &%  6>  % &% (   % ( '%  % ( % &% u 6 % &% (   % ( '%  % ( % &% u 6  % &% (   % ( '%  % ( % &% = 6  % &% (   % ( '%  % ( % &% 6  % &% (   % ( '% &% 6   % ( '% (  % ( % &% 6 % &% (   % ( '%  % ( % &% 6 % &% (   % ( '% &% 6  % ( '% (  % ( % &% 6k  % &% (   % ( '%  % ( % &% k 6 % &% (   % ( '% &% k6  % ( '% (  % ( % &% 6 % &% (   % ( '%  % ( % &% 6l % &% (   % ( '% &% 6l  % ( '% (  % ( % &% l6 % &% (   % ( '%  % ( % % % V09<  *   % %  6% % V,\:; !! % %  % %   % '%  % ( % % % V0KO_ 5 : 5 _ % % 8 6% % V,tMM: : % %  % %   % '% F CDIFVjCD0100ChemDraw 8.03C gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$d'`8'$$&3ÎV&x 7&w & 7&[ &v1d &-jNÊ 7&Q*  &   79'|&z &   :'Wɫ]T &&&&   +!Wn$T#`@NH+&   &   &   & &&& &&& &&rrO#`@N+&Zm  ;'&ī, !&Zm  +!ZM m&-s !#`@O-&Zm   & &&S &z j#`@O-'$ +,<_<# `O'$  ' '&' &&' &'nԾ#`NO2'\*!e 7<'tu*P26 Ȼz'\*!e  ='Z$``kt ' ' ' '\*!e "+!<*aZ*a'Vkt#`@NH+ '\*!e #  '\*!e $  '\*!e %  ' & ' '' ' ' '' ( ' 'B*a*a]m#`@N+':NuT )>'oO -Z':NuT ++!:.uzPu:PT-Z#`@O-':NuT , ' -''4u*Ptu*P[AwZ#`@O-'f) d .+  aB a26 h# `O'mv / ' 0''' 1''' 2''<*h|ÎV*h#`NO2'3 3+73cV3O# `O'X 4+7X%XE#`OH' 5&& !'$''' 6&& ' 7&& '#''' 8&&  ' 9&& '"'!'!' :&& "' ;&& #' <&& $' =&' %' >&'&' ?&' ''CJ.('~ A7)'t^ B7*'T ! C7+' D7,'d~ E7-'*L F7.' G(')' 3'FCDIF/'/' H)'*' 0' I*'+' /'1'1' J+',' 2' K,'-' 1'3'3' L-'(' 5'*,q M   6'p> N    ?'@' '' & 5'FDMHCGRTS11E x9 `}"M--N Ay BRfC|DEiFbV_/Y K K!1! +!3#64GHIJKL56 7 8 9 : ; <= > ? NO2NO2OOH `` !}!x" `` x33 `` g!v !qj" `` "V"$Times New Roman@@% ( % VjCD0100ChemDraw 8.03C gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`:'8$$&3ÎV&x 7&w & 7&[ &v1d &-jNÊ 7&Q*  &   7;'|&z &   <'Wɫ]T &&&&   +!Wn$T#`@NH+&   &   &   & &&& &&& &&rrO#`@N+&Zm  ='&ī, !&Zm  +!ZM m&-s !#`@O-&Zm   & &&S &z j#`@O-'$ +,<_<# `O'$  ' '&' &&' &'nԾ#`NO2'\*!e 7>'tu*P26 Ȼz'\*!e  ?'Z$``kt ' ' ' '\*!e "+!<*aZ*a'Vkt#`@NH+ '\*!e #  '\*!e $  '\*!e %  ' & ' '' ' ' '' ( ' 'B*a*a]m#`@N+':NuT )@'oO -Z':NuT ++!:.uzPu:PT-Z#`@O-':NuT , ' -''4u*Ptu*P[AwZ#`@O-'f) d .+  aB a26 h# `O'mv / ' 0''' 1''' 2''<*h|ÎV*h#`NO2'3 3+73cV3O# `O'X 4+7X%XE#`OH' 5&& !'$''' 6&& ' 7&& '#''' 8&&  ' 9&& '"'!'!' :&& "' ;&& #' <&& $' =&' %' >&'&' ?&' ''CJ.('~ A7)'t^ B7*'T ! C7+' D7,'d~ E7-'*L F7.' G(')' 3'/'/' H)'*' 0' I*'+' /'1'1' J+',' 2' K,'-' 1'3'3' L-'(' 5'*,q M   6'p> N    A'B' '' & 5'_1170149260.!mA. һһOle xEPRINT-/,ObjInfo0y VjCD0100ChemDraw 8.0f*Ѯ3Ss%ۨ @ @@3 :;<   `  33xx# $$$$2Times New RomanxXX$dg(XX$ddlNe[)x EMF,@  F Rf SKRp8Times New Roman^`$K$K^ I`$KP:w^`$KDwO;w<wp8wDwp}w9+ 9+4P\ Xplp;w )hwxw:w||dv%   &% 6 % &% (  b  % ( '% &% 6 b  % ( '% (  % ( % &% 6P % &% (  b  % ( '%  % ( % &% P6 % &% (  b  % ( '% &% P6 b  % ( '% (  % ( % &% 6 % &% (  b  % ( '%  % ( % &% 6P % &% (  b  % ( '% &% 6P b  % ( '% (  % ( % &% P6 % &% (  b  % ( '%  % ( % &%  6  % &% (  b  % ( '% &%  6  b  % ( '% (  % ( % &%  6E  % &% (  b  % ( '%  % ( % &% E 6  % &% (  b  % ( '% &% E 6  b  % ( '% (  % ( % &%  6  % &% (  b  % ( '%  % ( % &%  6E  % &% (  b  % ( '% &%  6E  b  % ( '% (  % ( % &% E 6  % &% (  b  % ( '% % a %  % ( % a RpTimes New Romanjw4 Hw2w`w6kws(uiwR w wL4P XplpDwX),\wxw:w||dv% a  TT=D@ڟ@a LPC2   TTEN@ڟ@ LPN8 % &%  6Y  % &% (    % ( '% % + %  % ( % + % +  TT We@ڟ@+ LPB2 b  TTWe@ڟ@b LPr % &% E 6E } % &% (  b  % ( '%  % ( % % % V0#  /   % %  6% % V,x ! ## % %  % %  b  % '%  % ( % % % V0/4j / 7 / zj % % 5 6 % % V,127   7 % %  % %  b  % '% FCDIFVjCD0100ChemDraw 8.0f*Ѯ3Ss%ۨ @ @@3 :;<   `  33xx# $$$$2Times New RomanxXX$dg(XX$d'` $$</Ѯ[_93:9+ ,7;̌P9+ -7=Y[ .7?̌PƔ /7A3:Ɣ 07Cf&0 17E 29; JFF 3;= G 4=? FHH 5?A I 6AC HJJ 7C9 Nf*e3Ss%ۨK3s99+f 87M O9+f 97OYx :Q OƔ ;7S3s9Ɣ <Uf.x =7]f.I D7 33*Ie&3Yf.I 'f.& (+f2&f*&Gf2Y# `Nf. )  * +f2f*̬2%ۨ#`CNe3sox F#+73Ssu3ku3Ss#`BrW >KM \XX ?MO Y @OQ XfZZ AQS [ BSU Z^\\ CUK ^ ES] f GOe g@A`2@A H   hN?N  I      < N hFDMHCGRTS 0 v  x P `5HI|8,9q:,;|<q= ]DqF ,J -"%.J/0%1>?@ABCEG 2 3 4 5 6 7CNBr ``  W !1 ``  3g. Times New RomanFMDLSKXY Times New Romand 0 !% D`D!% D_ID!% XD_dD!% E_ID!% E`D!% XDC '(.  ' '(.  ' '(.  ' 0!% _ED!% _EED!% kE`D!% UK ^ @S] f BOe g@A`2@A C   hN?N  D      < N h VjCD0100ChemDraw 8.0YWe3QW     X !"#$%&'()*+,-./0123456789:;<=>?@ABCDEFGHIJKLMNOPQRSTUVY\]^_`abcdefghijklmnopqrstuvwxyz{|}~lD  EMF[@  | G  KRp"TahomaB~ < ||||<|84B~tn|||{|| GO4P48<KKwX4<D  ||||<|dv%   % % &%  6   % &% (   % ( '% &% 6  % ( '% (  % ( % &%   6 % &% (   % ( '%  % ( % &% 6  % &% (   % ( '% &% y6   % ( '% (  % ( % &%  6 d % &% (   % ( '%  % ( % &%  d6  % &% (   % ( '%  % ( % &%  6. % &% (   % ( '% &%  6y  % ( '% (  % ( % &% .6  % &% (   % ( '%  % ( % &%  q6 q % &% (   % ( '% &%  V6 V  % ( '% (  % ( % &%  d6g  % &% (   % ( '%  % ( % &% g 6  % &% (   % ( '% &% \ 6   % ( '% (  % ( % &%  6  % &% (   % ( '%  % ( % &%  6b  % &% (   % ( '% &%  6X   % ( '% (  % ( % &% b 6 d % &% (   % ( '% FCDIFVjCD0100ChemDraw 8.0YWe3Q gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$d'`P)$$.)YWe3Q+)gv\ 7-)ܘ\ 7/)(ey 71)3j 73)n  5)j  77) y !7@)q )B)v{ +7D)JUaf ,7F)/ f -7H)xz .79) "+)-) ?):):) #-)/) ;) $/)1) :)<)<) %1)3) =) &3)5) >) '5)7) =)?)?) (7)+) A) *3)@) =)<)J)N)J) /@)B) K) 0B)D) J)L)L) 1D)F) M) 2F)H) L)N)N) 3H)@) F`TDMHCGRTSc  x9 `I#G#F"GD!H DJN! J"!H)Gg+G,I-J"."#$%&'(*/ 0 1 2 3Times New Roman@@FMDLSKXY Times New Romand 0!% ݏEBF !% ݏEF !% E F !% SEF !% EF !% SEF !% E2]F !% %tEF !% lE~F !% ._ETF !% _E7-F !% `lEKEF  '(. ' '(. ' ' '(. ' '( ' ' (. '  ' (. ' % ( % ObjInfo5CONTENTS_132748601518!mA. һһOle  gfg& @@3 :;<   `  QzG"x# $$$$8 @@Times New RomanxXX$dg(XX$dd'`R)8$$.)YWe3Q+)gv\ 7-)ܘ\ 7/)(ey 71)3j 73)n  5)j  77) y !7@)q )B)v{ +7D)JUaf ,7F)/ f -7H)xz .79) "+)-) ?):):) #-)/) ;) $/)1) :)<)<) %1)3) =) &3)5) >) '5)7) =)?)?) 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