ࡱ>  /1.yQ|%` bjbj"x"x 4J@@JJJJJJJ^f.f.f.f.l.T^`>2/3333444=======$?A>.644.6.6>33>777.633=7.6=77:<,JJ<3&/ !!Xf.6< c=|0>0><R~B7~B<~BJ<x4>=5,7i5$5444>>7 444`>.6.6.6.6^^^D^^^^^^JJJJJJ Problem Set 4 for Exam 4 Key Give an unambiguous IUPAC or common name for the following compound. Be sure to use cis/trans, E/Z or R/S where appropriate.  EMBED ChemDraw.Document.6.0  hex-(4E)-en-1-yn-(3S)-ol Draw the structure of the following alcohols: i) 3-methyl-2-buten-1-ol ii) cis-1,3-cyclohexanediol  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Which of the following compounds is more water-solubility? Explain why.  EMBED ACD.ChemSketch.20  or  EMBED ACD.ChemSketch.20  The alcohol on the right is more water-soluble. The more ball-like shape minimizes the non-polar surface area, so the proportion of polar to non-polar surface area is less than with the more linear molecule on the left. The left molecule also is larger (my mistake). Which of the following compounds has the higher boiling point? Explain why.  EMBED ACD.ChemSketch.20 or EMBED ACD.ChemSketch.20 Methylcyclohexane has only London dispersion forces to attract it to other molecules of itself. Cyclohexanol can hydrogen-bond to other molecules of itself, and has London dispersion forces, too, so it is higher boiling. More attractive forces implies more energy is needed to separate molecules. Which of the following compounds is the strongest acid, explain? A. B. C. D.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  C: The cyano group can delocalize the charge from the negative O after ionization. Write arrow-pushing mechanisms for each of the following reactions. a.  EMBED ACD.ChemSketch.20  Answer  EMBED ACD.ChemSketch.20  b.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  c)  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Give the major organic products of each of the following reactions. Show stereochemistry when needed. If no reaction will occur, write No Reaction.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  EMBED ChemDraw.Document.6.0  Show how the following products could be made from the indicated starting materials. Product Starting Material a.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  b.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  c.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  d.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Propose a multistep synthesis of the product shown below from the given starting materials, along with any reagents we have covered in class. You might discover multiple answers to this problem; draw only your best (one) synthetic route. 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TTrzԕ@@!LPH8 % % ]% ] TT|ԕ@@]LP3& % % %  TTԕ@@LPC8 % % z% z% z TTԕ@@zLPC8 % & % q6mq % & % (  z % ( ' % % z %  % ( % z % z  TTbqԕ@@z LPC8   TTbqԕ@@ LPH8 % %  %   TThtԕ@@ LP3& % % & % E6  % & % (    % ( ' % % t%  % ( % t% t TTԕ@@tLPC8  TTԕ@@LPl % & % q6gq % & % (   % ( ' % % z%  % ( % z% z TTԕ@@zLPC8  TTԕ@@LPH8 % % %  TTԕ@@LP3& % % & % 6? % & % (   % ( ' %  % ( % & % % *08% % *08% % *% % *ai% % *~% % *% F CDIFVjCD0100ChemDraw 8.0.3Ct]   @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$ Ct] mb UeU {+7KCt] #`CH3 UeU9 |+K5~5!r<# `C UeU9 ~+7K5Ct5MH#`CH3 UeUW +7KmS~mSUmb#`OHUeU9 +7K5Ct5MH#`CH3 }              4cYPmU  "   49UAX  "  YL$@@ +7f&YLf#`Cl@@ +f&YLf# `S@@ +7f&YLf#`Cl@@ +7f&XYX$# `O     &C8 'U0 +7˶C8 #`CH3(U03 +˶//!36# `C)U03 +7˘/C/ (B#`CH3*U0Q +!˶HMHMU%U# `O+U03 +7/C/ (B#`CH32U0o +˶kk!fzr# `S6U0Q +7MCM3T# `H9U0 +7H!2HX# `O;U0o +7˘kk!ft#`Cl, '( - () . (* / (+ 3 *2 7 *6 : 29< 2; 0⴬k=SЬ}O *"  8WfP *!  >_/, 9"  ?b";{̏ 9"  BxQ)lA\ +!7Y2sYYd#ClC_W[ A"  DTdQ.U A"  Eg i;i A"  F\O` A"  Gf_ A!  K;ADY!LMy P +7_$.T;A&.T#`CH3MMy n +F CDIF_$jj$1r# `CNMyn +7_j;j}#`CH3OMy  +7_$M$r{# `OPMy>n +7_Bj;:jD}#`CH3QMy  +_$::$ # `SSMy  +7""r{# `OTMy +7_ e#`ClU LM V MN W MO X MP Y OQ [ QS\ QT ]Hdz O"  _  S"  `Z%t3%!3 S"  j['"' O"  a(7*bm  +7#*q%?#Cllm +7S"|S"1# `Hm bl cK=Ĉ  b"  e,! me b"  f'+9 I' b"  sC>`C.tU6o +7#rC>`%r#`CH3uU6 +!#!#ѐ# `CvU6 +7C.#`CH3xU=6 +7AC9C.#`CH3| tu } uv  ux ڔZ u!  *YwU! +!7%U%&r# `OyU! +%!% A# `SzU! +7#!2X$r# `O{U +7^^! #`Cl wy  yz y{ ,E z"  b"';&! z"  2"K2"˱ w!  C`OUo +7rC`r#`CH3U +xx!3# `CU +7xCxˣ#`CH3U +"7xx!fް/An atom in this label has an invalid valence.#`ClU +7xCx#`CH3         Uô "  wLh  ""  G/{9 "  Ueսeb 5This F8*CDIFlabel has conflicting or unassignable charges.`+ SO2 + HCl$33@' 5This label has conflicting or unassignable charges. +"4Mp     ! |$(H     ! %@@    H*SS     ! IзsXHO     ! J    q#~h     ! r  5    )|k%     ! @`8     ! @O    F DMHCGRTS'  x (XP`5 ` 3(  \, =\73Cx gDZ 1 " " S"/"2#? >#K  Qp y   )0()L) ()? $##u##)w-g4^8;#l ~ 5  H Q _b^; ` bdk""  P " ]% /M/xx   `(`&K1!S#1!SqB    WQ QW   1 1Y 1 "{ z| z~ 3z     !""#"$%&}&'&(&)CH3CCH3ClCH3OSOCl CH3 C CH3 CH3 ClHCH3CCH3OCH3SOClClCH3CCH3OCH3SHO Cl!Cl"S#Cl$O%CH3&C'CH3(OH)CH3 `` ""Z## `` " "Z " M ``   0 `` " "Z "  `` %N $ %{ 0 `` W% `` Wq `` 939 ``  `` * ``  *  P `` n   3 ``   K 3  (() `` &[&[& `` :  `` [;[ `` [[ `` ;I `` /[[\ `` !;!! `` #]#]# `` ! ! !   `` G |t `` G JG ``   S + `` G  N `` + `` Gl lJ ``  `` # *U ``  g Sg # ``  Z  `` N Q r ``     `` N : :V  `` )j Vj `` )2 2, ``  2 52  `` ) 0 `` 22 `` ""9#) + SO2 + HCl     >+ArialTimes New RomanF MDLSK XY Ariald 0 j XWS Times New Roman x+ SO2 + HCl 0 Y  XC?Times New Romanx+ 0 !%b CD!% UDD!%b UD>D!O%b UZDD!%b UDUE '  '  '  '  0!Cl% DD!S% DD!Cl% DE!O% DD '  '  ' (  0!%b >-ED!% ?ED!%b ?ED!O% RED!%b ?EUE!S% ~eED!H% REUE!O% >xED!Cl% ~eED '  '  '  '  '  '  ' (.  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(* / (+ 3 *2 7 *6 : 29< 2; 0⴬k=SЬ}O *"  8WfP *!  >_/, 9"  ?b";{̏ 9"  BxQ)lA\ +!7Y2sYYd#ClC_W[ A"  DTdQ.U A"  Eg i;i A"  F\O` A"  Gf_ A!  K;ADY!LMy P +7_$.T;A&.T#`CH3MMy n +_$jj$1r# `CNMyn +7_j;j}#`CH3OMy  +7_$M$r{# `OPMy>n +7_Bj;:jD}#`CH3QMy  +_$::$ # `SSMy  +7""r{# `OTMy +7_ e#`ClU LM V MN W MO X MP Y OQ [ QS\ QT ]Hdz O"  _  S"  `Z%t3%!3 S"  j['"' O"  a(7*bm  +7#*q%?#Cllm +7S"|S"1# `Hm bl cK=Ĉ  b"  e,! me b"  f'+9 I' b"  sC>`C.tU6o +7#rC>`%r#`CH3uU6 +!#!#ѐ# `CvU6 +7C.#`CH3xU=6 +7AC9C.#`CH3| tu } uv  ux ڔZ u!  *YwU! +!7%U%&r# `OyU! +%!% A# `SzU! +7#!2X$r# `O{U +7^^! #`Cl wy  yz y{ ,E z"  b"';&! z"  2"K2"˱ w!  C`OUo +7rC`r#`CH3U +xx!3# `CU +7xCxˣ#`CH3U +"7xx!fް/An atom in this label has an invalid valence.#`ClU +7xCx#`CH3         Uô "  wLh  ""  G/{9 "  Ueսeb 5This label has conflicting or unassignable charges.`+ SO2 + HCl$33@' 5This label has conflicting or unassignable charges. +"4Mp     ! |$(H     ! %@@    H*SS     ! IзsXHO     ! J    q#~h     ! r  5    )|k%     ! @`8     ! @O    EPRINTSUXDNObjInfoVCONTENTSC _1290166439Y!mA. !X!Xl2 EMFDN,p     kKRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   % !% !Rp"Arial M@MȻ::|X: ||||:|dv% ! TT8 G+@Z@!LPH8 ] TT 8G+@Z@]LPO? % &% Vx6 % &% (  ] % ( '%  % ( % &% /6Vx % &% (  ] % ( '%  % ( % &% x6/ % &% (  ] % ( '%  % ( % &% 6x % &% (  ] % ( '% % %  % ( % %  TTL[+@Z@LPO?  TTL[+@Z@LPH8 % &% a6 % &% (   % ( '%  % ( % % % V00K>R Y} n Y} B Y% %  X6X% % V,N2P ]]U U% %  % %   % '% % 'T%  % ( % 'T% 'T TT'+@Z@'TLPC8 cT TT'+@Z@cTLPl % % T% T% T TT'+@Z@TLPS8 % &% 363 % &% (  T % ( '% % %  % ( % %  TT+@Z@LPO? % &% 6 % &% (   % ( '% &%  6   % ( '% ( % %  % ( % %  TT0?+@Z@LPO? % &%  e6  % &% (   % ( '% &% e6  % ( '% (  % ( % &% )363 % &% (   % ( '%  % ( % &% 36 % &% (   % ( '% &% 36  % ( '% (  % ( % &% 6{  % &% (   % ( '%  % ( % &% { 6 3 % &% (   % ( '% &% o 6 3  % ( '% (  % ( % &%  36{  % &% (   % ( '%  % ( % &% { 6 % &% (   % ( '% &% o 6  % ( '% (  % ( % &% 63 % &% (   % ( '% % ? T%  % ( % ? T% ? T TTOW'+@Z@? TLPC8 { T TTYa'+@Z@{ TLPH8 % Rpj"Arial|HQ@b@b@|b@R@@Q@ MMȻ:QX:||||:|dv%  fRp"Arial|8|2|||`D:2|H:M\:iδMb@LH M MȻ:XL:b@||||:|dv%  f TTbg*+@Z@ fLP3& % % &%  362 3 % &% (   f % ( '% % %  % ( % %  TT\k+@Z@LPN8 % &% +66+ % &% (   % ( '% &% @C6@  % ( '% (  % ( % &% +6F % &% (   % ( '%  % ( % &% F6d  % &% (   % ( '% &% -6N   % ( '% (  % ( % &% d 6d 6 % &% (   % ( '%  % ( % &% d 66 % &% (   % ( '% &% N C6   % ( '% (  % ( % &% 6+6 % &% (   % ( '% %  %  % ( %  %   TT(7+@Z@ LPO ? % &% Q 6Q  % &% (    % ( '%  % ( % &% Q 6? ) % &% (    % ( '%  % ( % &% ? )6 _ % &% (    % ( '%  % ( % &%  _6[  % &% (    % ( '%  % ( % &%  6Q  % &% (    % ( '% FT H CDIFVjCD0100ChemDraw 8.0.3YLhApDh  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$YvhA`@zL =+7f&~hPYvhA~hP#`OH@{f >7@z&v @7@9q B7@zLl D7@`g F+7f&`Y``#`OH ?  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Arialj lww 0w f-Arial mww 0w f-2 C 2 C 2 :C $2 H Arial ww 0w f- 2 $3 -2 _CH-2 2H- 2 CH$2 HH- 2 #3H-% % **% %c%Z7-%"Systemך f &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qOle10Native_1223036518oeF!X!XOle CompObjnp h''n',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ ^ T)? D@D!C)? D@D!C#? D?D!+? $D@D!CH2#?D@D!??s?jG? eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qN''8',Arial,Arial, ,vArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ObjInfoq"Ole10Native#R_1223295837teF!X!XOle 5  )?CD!C)?DD!C#?CD!#?-DD!?5??c">DD@DD BDD@}DD_DPDBDD@}DDBDD@}DDAFT1. NaNH2 2. #?TDD!?oDD!#?!#?!?CH2CH3?@u@w   --PRINTsv6VCompObjDhObjInfouwFOle10NativeG0"Systemf !T-.  Arial lww 0wf-Arial œww 0wf-2 cC2 chC 2 cH$ 2 O' 2 hH$ 2 hH$-%c %%%h%h)%h%Jh)%J-%7e%7e%z7ze%zz"Systemf &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q,''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ ^  )?@DD!C)?`DD!C#?DD!#?ED!#?HDD!#?/DGD!#?h|DD!#?{D9`D!#?;DD!#?[DD!#?[D`D! ?Y?+??n??<Mn?<?<<M?BB? ? a3 eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q_12230366948zeF!X!XOle \CompObjy{]hObjInfo|_Ole10Native`_1223295911geF!X!XOle sPRINT~tR''',Arial,Arial, ,vArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ 3)?D`D!C)?oC`D!C#?D_D!#?oC`D!#?XK-DD!#?K-DקD!#?FDD!#?FD9D!?cc?wc+c?Pcc?wc? wc??. ?."@UD`DD`D @]DDDD D0D@]DDDD@]DDDDAFTHOH, HgO (cat.)H2SO4 (cat.)   j --"Systemf0 !T-.  Arial plww 0wf0-Arial jww 0wf0-2 C2 C 2 0/H$ 2 0iH$-%%%32 %B%|%2%FB%B%cF%5%5c%|%F|%5%ZF%Z5"System0f0 &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $CompObjhObjInfoOle10Native_1223037048eF!X!X^ )?`D8E!C)?E8E!C#?E+>E!#?E8t3E!#?0D7t3E!#?/D+>E!#?sE3-E!#?T E2E!#? EV)E!#?h E,E!#?xD2E!#?8D(-E!#?NDP,E!#?D1)E!?  ?1  ?@7 s ?z7 s ?  ? @7 ?- @7 ?a  ?  - ?  a ? - z7 ?  z7 ?  - ? X  ? X   eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial, ,vOle CompObjhObjInfoOle10NativeArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ ] )?wD E!C)?oC E!C#?73D E!#?oC E!#?XBD <E!#?BDE!#?[D/E!#?\D E!#?HC <E!#?HCE!#?kC/E!#?_kC E! ?S??? 4 ? ?p 4 ?p ?pp ?Q4 ? Q?  Q4 ? Q?  "qD0ED0E tDE@DE@D EtDE@DEtDE@DEAFTH2 , Pd-BaSO4  Quinoline>   _1223295970eF!X!XOle PRINT&CompObjh--"Systemfy !T-.  Arial lww 0wfy-Arial  Ըww 0wfy- 2 :C$2 HArial &ww 0wfy- 2 $3- 2 O'2 H 2 :O'-%c%%M%M%F7F%T7T"Systemyfy &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,ObjInfoOle10Native_1223037325eF!X!XOle Arial,Arial,Arial,Arial,Arial,Arial, $^ #?ǵCY;E!#?^CZ8E!#?DZ;E!#?0D\8E!#?0D^;E!#?1D\t2E!?  ?  ?m  ? m ?mB m  eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''', Arial,Arial,Arial, ,CompObjhObjInfoOle10Native_1223296820eF!X!XvArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ #?XC&E!#?Q>C#E!#?ED&E!#?"i'D#E!?8 ` ?Bm 8 ?D Bm "@=D"ED"E ;DED-E_D%E;DEDE;DEDEAFT  1. Mg, ether2. CO2 3. H3O+ . w  R --Ole PRINT4CompObjhObjInfo"Systemf !T-.  Arialv lww 0wf-Arial3 ww 0wf- 2 C$2 HArial _ww 0wf- 2 ;3- 2 O'-%N%ZN%Z%NZ%Z%N%*N%%"Systemf &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qX''B',Arial,Arial,Arial,Arial,AriOle10Native\_1223037693eF!X!XOle CompObjh      !"#$%&'),-./012345678;>?@ABCDEFGHIJKLMNQRSTUVWXYZ[\^abcdefghijklorstuvwxyz{|}~al,Arial,Arial, $^ '#?wDC!#?wD~C!#?ڿDB!#?ڿDC!#?zDC!#?zD~C!#?//DQB!#?-/D;C!??>j?>0?>j?>0??x?" eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qObjInfoOle10Nativev_1223296850eF!X!XOle r''\',Arial,Arial, ,vArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ '#?CC!#?CC!#?[CC!#?[CC!#?wCC!#?wCC!#?UDC!#?QD?C!?[?&[??0[&?0?00[?-3[?,"1DCkDC 4DCgDCNDC4DCgDC4DCgDCAFTCrO3 Pyridine M  C --"System f !T-.  Arial lww 0w f-Arial wPRINT&CompObj(hObjInfo*Ole10Native+\w 0w f- 2 C $2 H Arialm Sww 0w f- 2 ,3 - 2 wBr!-%b%Z0b%Z%bZ0%Z%b%3b%b"System f &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qX''B',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ '#?DD!#?D.D!#?_D D!#?_D;D!#?PkDD!#?PkD.D!#?DD!#?"D@"D!?YYX?&YX?Y?X&??X?)YX?}YX eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qN''8',Arial, ,vArial,Arial,Arial,Arial,Aria_1223037759eF!X!XOle 9CompObj:hObjInfo<Ole10Native=R_1223296880eF!X!XOle OPRINTP l,Arial,Arial, $^ '#?CED!#?C@`D!#?[C8D!#?[CmD!#?wCED!#?wC@`D!#?UD8D!#?QD mD!????,?,?,,?)?("2DTD@~DTD 3D@CD@vDgDUDUD3D@CD@vD@CD3D@CD@vD@CDAFT  Conc. H-Brheat.   R --"System f !T-.  Arialj lww 0w f-Ariall ˸ww 0w f- 2 C $2 H Arialv ww 0w f- 2 ;3 -%N%[%ZN%Z%NZ%Z%N%*N"System f &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qCompObj]hObjInfo_Ole10Native`_1223037893eF!X!X''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ #?DB!#?D_C!#?DB!#?DC!#?\hDB!#?\hD_C!#?/DQB!?}?K}??C}K?C?CC}?-Y} eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qOle mCompObjnhObjInfopOle10Nativeq''u',Arial,Arial, ,vArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ '#?fC D!#?fC`D!#?[CD!#?[CD!#?wC D!#?wC`D!#?U&DD!#?Q&DD!?C??xC?5?5Cx?5C5?2?1jC"@4DD DD 8DDD`D@mDD8DDDD8DDDDAFTConc. H2SO4 (cat.)heatS    * --"Systemc f !T-. _1223296933eF!X!XOle PRINT8CompObjh Arial ylww 0wc f-Arial rww 0wc f- 2 5C $2 5)H ArialF ww 0wc f- 2 MM3 - 2 O ' 2 H $ 2 >H $ 2 jS ! 2 gO ' 2 lgO ' 2 C $2 H - 2 !3 -%%_Q%_%%_Q%_%%---$h^T-%h^T-% %%% %%%%<<%GG%RR%]]%hh%ss%~~--$@@@-%@@@-%e%0%%ss % %n@%sns@%%%"Systemc f &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qObjInfoOle10Native_1223038099eF!X!XOle ''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^     P O !"#$%&'()*+,-./0123456789:;<=>?@ABCDEFGHIJKLMRQSR_bUVWXYZ[\]^`avxdefghijklmnopqrstuwz{|}~^ #?EDP9E!#?ED?E!#?[C6E!#?[C@CE!#?wCP9E!#?wC?E!#?UD5E!#?QD@CE!#?D2E!#?DFE!#?6D@CE!#?6D=E!#?6DpIE!#?OD@CE!?  ?`  ?4  ?d ` ?d 4 ?d d ? am ? `& ? F ?  O ? 4 4 ?   ? } O ? '4 4  eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial, ,Arial,Arial,Arial,Arial,AriaCompObjhObjInfoOle10Native_12232969934eF!X!Xl,Arial,Arial, $^  #?C@D!#?CD!#?[CD!#?[C D!#?wC@D!#?wCD!#?UfDD!#?QfD D!#?CD!#?CD! ?z?Ez??>zE?>?>>z?z;R?: ?z+? 4"@1D@DD@D @#?@uD D!#?ZD D!#?ZDD!#?ZD`D!#?@@D D!?ii?kkO?kk?$iViw??CDDqDDZD0DCDDqDDCDDqDDAFTPyridine%%   S Ole PRINT4CompObjhObjInfo--"Systemf !T-.  Arial Zlww 0wf-Arial :ww 0wf- 2 j:C$2 jHArial Ǹww 0wf- 2 $3-2 jCH-2 2H- 2 OH'2 HH-%c%%v%_%_%7lArial ww 0wf- 2 y*+- 2 vO'2 vlH 2 vC$2 vH- 2 <3-%"Systemf &---' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,KArial,Arial,Arial,Arial,Arial,Arial,Arial, $Arial,Arial,Arial,Arial,Ole10Native_1223038347eF!X!XOle CompObjhArial,Arial,Arial, $^ ^ #?@DPE!#?DE!#?3DPE!#?DE!+?<&DPE!CH2#??&D`D!?zqR? =r?mzE?Rmz?+p??DxEDED@EDxEDxEDxEDxEAFT+w#? 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TT@@LPHE  TT@@LP,  TT@@LP  1 TT@@1LPT8 o TT@@oLPH,E  TT@@LPF8 % % % % % %  TT+=@@LP22  TT+=@@LP.  TT+=@@LP  % % % % j% j TT(6@@jLP- % % % %  TT+=@@LPOK \ TT+=@@\LPHE  TT+=@@LP/ee  TT+=@@LPHE % % %  TT2@@@LP2ee& % % .% . TT+=@@.LPOeeK % % v% v TT2@@@vLP2& % % FCDIFVjCD0100ChemDraw 8.0.3nb;f 4 @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`#$$nb;mx1 xO 7xm 7kbkI 7" 7         @n3d3pf &ChemDraw can't interpret this label.`1. Sia2BH, THF!@3 &ChemDraw can't interpret this label.+@`2. -OH/H2O2xx    F|pDMHCGRTS(;  x (XP`5 o; o  ` `6 `5 g ``   1. Sia2BH, THF  @@ ``    , 2. -OH/H2O2ArialTimes New RomanFthMDLSKXY Ariald 0 MPiX]YTimes New Roman x1. Sia2BH, THF 0 X Times New RomanxTimes New RomanxTimes New Roman x2. -OH/H2O2 0 !% CD!% FDD!% DD!% oCvD!% CyD '  ' (  '  ' 0 89d2 % % $ArialTimes New RomanxXXrjVg(XXrdd'`'$$nb;mx1 xO 7xm 7kbkI 7" 7         @n3d3pf &ChemDraw can't interpret this label.`1. Sia2BH, THF!@3 &ChemDraw can't interpret this label.+@`2. -OH/H2O2xx    _1290162684O!mA. ` !X` !XOle ?EPRINT@ObjInfo|/  lcL EMF,p  { f K % % &%  6\ H % &% (   % ( '%  % ( % &% \ H6V H % &% (   % ( '% &% h *6V *  % ( '% (  % ( % &%  6  % &% (   % ( '%  % ( % &%  6 % &% (   % ( '%  % ( % &%  6 % &% (   % ( '%  % ( % &% V H6  % &% (   % ( '% FCDIFVjCD0100ChemDraw 8.0.3 Gq g4 @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$ Gq) 6> 76\ 7) 7   7 kIk 7))mq 7                 FDMHCGRTS/JDf  x (XP`54zz4 z4)"ArialTimes New RomanFdWMDLSKXY Ariald 0 !% 9E D!% FE E!% YE E!% 9ED!% &E D!% ],EƛD!% :fE:E '  ' (.  '  '  '  ' % ( %  VjCD0100ChemDraw 8.0.3 Gq g4 @@' :;<   `  3CONTENTS}_1290156231!mA. ` !X` !XOle EPRINTTxx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$ Gq) 6> 76\ 7) 7   7 kIk 7))mq 7                  VjCD0100ChemDraw 8.0.3nb;lB EMFT,p  U E #KRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% 6 % &% (  O % ( '%  % ( % &% 6 % &% (  O % ( '% &% 6 O % ( '% ( &% 6 O % ( '% (  % ( % &% 66 % &% (  O % ( '%  % ( % &% 6 % &% (  O % ( '%  % ( % % % V0$pzp% % x6% % V, !zz% %  % %  O % '% % 3%  % ( % 3RpTimes New Roman HMx:1:|X:||||:|dv% 3 TTʕ@@3LPLe8 q TTʕ@@qLPi  TTʕ@@LP,  TTʕ@@LP   TTʕ@@LPNK  TTʕ@@LPHE % RpLTimes New Roman|8|2|||$h|2||| FpHn"0: XMx:0U:Xf:Hn$||||:|dv% ORpTimes New Romanw!-(wMw:w!-!rZ(|xHMLM\: δMf@(P (Mx:P4X:f@||||:|dv% O TTʕ@@OLP3& % % &% 6 % &% (  O % ( '%  % ( % &% 6 % &% (  O % ( '% F~CDIFVjCD0100ChemDraw 8.0.3nb; 4s͌ @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`)$$nb;x1 xO 7xm 7kbkI 7" 7$x 7&x 7        % $ ' &  r3ht@ &ChemDraw can't interpret this label.`Li, NH3xx    FL>DMHCGRTS(:  x (XP`5 o; o  ` `6 `5 g ` `  ``  {- v }Li, NH3ArialTimes New RomanFMDLSKXY Ariald 0 ;XOKTimes New Roman xLi, NH3 0 !% CD!% FDD!% DD!% oCvD!% CyD!% CCD!% `DD '  ' (  '  '  '  ' 0 89d2 % ( % ObjInfoCONTENTSy_1290163113!mA. ` !X` !XOle  4s͌ @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`+$$nb;x1 xO 7xm 7kbkI 7" 7$x 7&x 7        % $ ' &  r3ht@ &ChemDraw can't interpret this label.`Li, NH3xx     VjCD0100ChemDraw 8.0.3 O3Ɗ 4g @@' :;<   `  3xx# $$$$2$ArialTEPRINTObjInfoCONTENTS_1290157907!mA. ` !X` !XlCA EMF,p   F %KRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   &% V6! % &% (   w % ( '%  % ( % &%  6V % &% (   w % ( '%  % ( % &%  V6  % &% (   w % ( '%  % ( % &%  6 V % &% (   w % ( '%  % ( % &%  6  % &% (   w % ( '% % < w%  % ( % < wRp"Arial M@MȻ::|X: ||||:|dv% < w TTH@@< wLPO? } w TTH@@} wLPT,  w TTH@@ wLPs, % &%  63 n % &% (   w % ( '% FCDIFVjCD0100ChemDraw 8.0.3 O3Ɗ 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$ O3Ɗ3P @73c A73v- C3G E73a G73v- I73{ K733Y333{ (+ٶw w33{# `O3Ǚ )FǨ *F +2 , -Ǩ .2 /3{ 0+kx kx# `S3{ 1+w w33{# `O3] 2+Y Y33|a# `O3a 3  4 5 6  7 8  9 :  ; < = > ?٧w wD$Ɗ#`OTs B  D  F  H  J  L F8*DMHCGRTS,E:m  x (XP`5 @ A C E GRI KBDFHJLOTs ``  ] ] "ArialTimes New RomanFMDLSKXY Ariald 0 !% 2,ED!% i,ED!%  ??2@ݝ#TsCls3sY3s+ O&ChemDraw can't interpret this label.Pyridineo6 M   FDMHCGRTStW  x (XP`5"B"M!UN"U@!n ]A" dC!n lE"sG$ dI!n{KBDFHJLTsClOH  !t  ! `` !-! -!Y  #77O"|2#jdPyridineArialTimes New RomanF|oMDLSKXY Ariald 0  > XQMTimes New RomanxPyridine 0 !% ȰjDlE!% <ҕDE!% LDlE!% DE!% ?DlE!% LD̓E!O%b EE '  '  '  '  '  '  0!TsCl!% DEԅE!% h;Ek{E!% (Ek{E!% HEԅE!% (EvE!% h;EvE!% EԅE!S% WEԅE!O% WExE!O% WE4E!Cl% HjEԅE ' (.  '  ' (.  '  ' (.  '  '  '  ' (  '  (  '  "4TsCl6= "E`E<0 !  89d2 % % VjCD0100ChemDraw 8.0.32O]3@9 Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$a O]3b3P] *7c3cw +7d3v֑ -e3ѫ /7f3 17g3v֑ 37h3 5+7ٯ 33#`OHi ,cb j .dc k 0ed l 2fe m 4dg n 6fh r2@ݝq@ 87Y|x?: yD+ zD  {? |;  };+ ~? ?X +e&}UY}UL#\# `S?X +e&TYTe\# `O?X +e&TYTe\ `O?v +e&AsYAsL|#`Cl xy  yz z{   {| !|}  "x} #{~ $x % & '?2@ݝ#TsCls3sY3s+ 9&ChemDraw can't interpret this label.Pyridineo6 7   _1290163247 !mA. ` !X` !XOle EPRINT(ObjInfolDA EMF(,p   F QKRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   &% =q6d % &% (   % ( '%  % ( % &% 6=q % &% (   % ( '%  % ( % &% q6 % &% (   % ( '% % %  % ( % Rp"Arial M@MȻ::|X: ||||:|dv%  TT۹@ŗ@LPB8  TT۹@ŗ@LPr % &% 6q % &% (   % ( '%  % ( % &% =q6=l % &% (   % ( '% FCDIFVjCD0100ChemDraw 8.0.3#*T2 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$#*T2'*  76D '^ 76߻x 7' #+7ff+2#23+2#`BrTD 7          F$DMHCGRTS *  x (XP`5+W ,B_+g,B n+ v._Br `` +c /* /+i ArialTimes New RomanF<-MDLSKXY Ariald 0 !% >CXE!% N+DE!% lDXE!% DE!#Br% dDXE!% N+DhE '  '  '  '  ' % ( %  VjCD0100ChemDraw 8.0.3#*T2 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`CONTENTS_1290157919!mA. ` !X` !XOle EPRINT     "#$%&'()*+,-./0126789:;<=>?@ABCDEFGHIJKLMNOSTUVWXYZ[\]^_`aefghijklmnopqrstuvwxyz{|}~$$#*T2'*  76D '^ 76߻x 7' #+7ff+2#23+2#`BrTD 7           VjCD0100ChemDraw 8.0.323TT3@ Y @@' :;<   `  3xx# $$$$2$ArialTlDY EMF,p    G  KRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &%  67  % &% (  w  % ( '%  % ( % &% v8 6  % &% (  w  % ( '%  % ( % &% O 6v8  % &% (  w  % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% Y %  % ( % Y Rp"Arial M@MȻ::|X: ||||:|dv% Y  TT@7@Y LPO? HY  TT@7@HY LPH8 % &% P 6O  % &% (  HY  % ( '%  % ( % &%  6  % &% (  HY  % ( '%  % ( % % % V0""    " % %  6/ % % V,  . .  % %  % %  HY  % '% % y` %  % ( % y` RpTimes New Roman HMx:1:|X:||||:|dv% y`  TT@7@y` LPP8 `  TT@7@` LPB? `  TT@7@` LPr % RpLTimes New Roman|8|2|||$h|2||| FpHn"0: XMx:0U:Xf:Hn$||||:|dv% w RpTimes New Romanw!-(wMw:w!-!rZ(|xHMLM\: δMf@(P (Mx:P4X:f@||||:|dv% w  TT@7@w LP3& % % FCDIFVjCD0100ChemDraw 8.0.323TT3@ Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$OTT3&"P3XU 7Q3go  R3X "7S3g $7T3X& &+7\&"T&"3\&"#`OHU3o (7V !QP W #RQ X %SR Y 'TS Z )QU ^23T@?`f]X +7:wC xX +\C2TC ]e# `Py> #+BC:CCC #`Brzr #+vCEnCwC #`Br{X #+\2T ]#`Br| xy} xz~ x{]23T@?`f#`PBr3[ii *   FthDMHCGRTS^lN  x (XP`5>>:*/+  " $&q(!#%')PBr3OH `` M `` ;vvBArialTimes New RomanFxMDLSKXY Ariald 0 !% TDpWE!% (ߊD`E!% YDpWE!% D`E!O%b LDpWE!% (ߊDsE '  '  '  '  '  0!PBr3!P% EWE!#Br% <$EKGE!#Br% <$EgE!#Br% EWE '  '  ' "4PBr36= }EWE<0 89d2 % % ObjInfoCONTENTS_1290163149!mA. ` !X` !XOle imes New RomanxXXrjVg(XXrdd'`$$OTT3&"P3XU 7Q3go R3X 7S3g 7T3X& +7\&"T&"3\&"#`OHU3o !7V QP W RQ X SR Y  TS Z "QU ^23T@?`f]X $7:wC xX +\C2TC ]e# `Py> #+BC:CCC #`Brzr #+vCEnCwC #`Br{X #+\2T ]#`Br| xy} xz~ x{]23T@?`f#`PBr3[ii #   EPRINT\ObjInfo CONTENTS!h_1290157932!mA. ` !X` !XlK EMF\,p  } L H KRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   &% 3 J6Z  % &% (    % ( '%  % ( % &%  63 J % &% (    % ( '%  % ( % &%  J6  % &% (    % ( '%  % ( % &%  6 J % &% (    % ( '% % w k%  % ( % w kRp"Arial M@MȻ::|X: ||||:|dv% w k TTP@UU@w kLPH9 % &%  6h e % &% (  w k % ( '% %  %  % ( %  %   TT<KP@UU@ LPO? % &%  6  % &% (    % ( '% &%  6    % ( '% ( F|mCDIFVjCD0100ChemDraw 8.0.3!O 3/ 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$!O 3/3 P` 73c[9 73 vVS 3Qm 73 L 3G +7!# `H3+L +7/d'd3/h1# `O           FhZDMHCGRTSEOTt  x (XP`5s{ iHO `` 3 Q Q3  `` CCArialTimes New RomanFtgMDLSKXY Ariald 0 !% 23E(E!% CE0E!% TE(E!% RdE0E!% tE(E!H% gfE0E!O% tEP;E '  '  '  '  '  ' ( % ( %  VjCD0100ChemDraw 8.0.3!O 3/ 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$!O 3/3 P` 73c[9 73 vVS 3Qm 73 L 3G +7!# `H3+L +7/d'd3/h1# `O            VjCD0100ChemDraw 8.0.3S2/ Y @@' :;<   `  3Ole 3EPRINTObjInfo4CONTENTS5   +, !"#$%&'()*1-.0<>3456789:;=N@ABCDEFGHIJKLMOPSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~l#C "A EMF,p  D )F MKRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% 6 % &% (   % ( '%  % ( % &% m6 % &% (   % ( '%  % ( % &% F6m % &% (   % ( '%  % ( % &% 6F % &% (   % ( '%  % ( % &% m6m  % &% (   % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% %  % ( % Rp"Arial M@MȻ::|X: ||||:|dv%  TT@ŗ@LPO?  TT@ŗ@LPH8 % &% 6 % &% (   % ( '%  % ( % % % V0# w  w  % %  6% % V,  % %  % %   % '% % A%  % ( % ARpTimes New Roman HMx:1:|X:||||:|dv% A TT@ŗ@ALPP8 x TT@ŗ@xLPCE  TT@ŗ@LPCE % FCDIFVjCD0100ChemDraw 8.0.3S2/ Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`~$$:S2`9T 7;m 7=&  ?9 "7AL $7C2& &7I` (+7f``@ `#`OH< ;9 > !=; @ #?= B %A? D '=C J )AI N2@ f&MY +7lBF"xv +{{5e"# `Pyv  +c cBF"# `Czv  +l lB# `C{ xy| xz 2@ f&/An atom in this label has an invalid valence.#PCCK, *   FxDMHCGRTSGUT  x (XP`5cc*~+d d "$ &d(!#%')PCCOH  ! `` ggArialTimes New RomanFdUMDLSKXY Ariald 0 !% RD,E!% yD #E!% D,E!% mD #E!% _D,E!% D@?E!O%b E #E '  '  '  '  '  '  0!PCC!P% #EE!% \3E!(E!% E!(E '  ' "4PCC6= } E#E<0 g 89d2 % % xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`~$$:S2`9T 7;m 7=& ?9 7AL 7C2& !7I` #+7f``@ `#`OH< ;9 > =; @ ?= B  A? D "=C J $AI N2@ f&MY &7lBF"xv +{{5e"# `Pyv  +c cBF"# `Czv  +l lB `C{ xy| xz 2@ f&/An atom in this label has an invalid valence.#PCCK, %   _1290163174!mA. ` !X` !XOle PEPRINT(ObjInfoQ VjCD0100ChemDraw 8.0.3E3v 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrlCeA EMF(,p   F  KRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   &%  8 6  % &% (  f  % ( '%  % ( % &%  6 8  % &% (  f  % ( '%  % ( % &% p 8 6  % &% (  f  % ( '% % * %  % ( % * Rp"Arial M@MȻ::|X: ||||:|dv% *  TTו@ŗ@* LPC8 f  TTו@ŗ@f LPl % &% ! 6p 8  % &% (  f  % ( '%  % ( % &%  8 6 3  % &% (  f  % ( '% FCDIFVjCD0100ChemDraw 8.0.3E3v 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$E3v3I]  73XX+ 3ITE 73XO_ 73I&Jy +7M&uE&uM#`Cl3vX+ 7          F$DMHCGRTSZKhj  x (XP`5[ bjryEbCl `` 1s1ArialTimes New RomanF<-MDLSKXY Ariald 0 !% *ENE!% ;EpWE!% TKENE!% l[EpWE!Cl% XkENE!% ;E0jE '  '  '  '  ' % ( % CONTENTSR_1290157944 !mA. ` !X` !XOle bEPRINT dd'`$$E3v3I]  73XX+ 3ITE 73XO_ 73I&Jy +7M&uE&uM#`Cl3vX+ 7           VjCD0100ChemDraw 8.0.32?I@  Y @@' :;<   `  3xx# $$$$2lWF EMF ,p  v2 Y QjKRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% =6d % &% (   % ( '%  % ( % &% 6= % &% (   % ( '%  % ( % &% 6 % &% (   % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% 5%  % ( % 5Rp"Arial M@MȻ::|X: ||||:|dv% 5 TT""@×@5LPO? 5 TT""@×@5LPHM8 % &% ,6 % &% (  5 % ( '%  % ( % % % V0Q)\Q% % Z6% % V,\\% %  % %  5 % '% % %  % ( % RpTimes New Roman HMx:1:|X:||||:|dv%  TT"@×@LPS8 & TT"@×@&LPOK o TT"@×@oLPCE  TT"@×@LPl) % RpLTimes New Roman|8|2|||$h|2||| FpHn"0: XMx:0U:Xf:Hn$||||:|dv% RpTimes New Romanw!-(wMw:w!-!rZ(|xHMLM\: δMf@(P (Mx:P4X:f@||||:|dv%  TT"@×@LP2& % % &% =6= % &% (   % ( '% FCDIFVjCD0100ChemDraw 8.0.32?I@  Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$*?IL)I 7+{c  -&v} "7/9q $71Ll &+7fLL@L#`OH7{c *7, !+) . #-+ 0 %/- 2 '1/ 8 ++7 622f&5YH )7xpxaexYG +?2sefe# `Sy^tG +Dx_xp_x,# `OzTG +;Enxae#`Cl{YG +?_2sef_#`Cl| xy} xz~ x{22f&#+`SOCl23  (   FxjDMHCGRTS&7J  x (XP`5 0 0( ) 0 \ 0 " \ $ 0 &*!#%'+SOCl2OH ``  {*   ``  } ArialTimes New RomanFMDLSKXY Ariald 0 !% 7DD!% xDD!% ӜDD!% MDD!O%b _DD!% xD@D '  '  '  '  '  0!SOCl2!S% ED!O% E(vD!Cl% EiD!Cl% DD ' (  '  ' "4SOCl26= -ED<0 _ 89d2 % ( % ObjInfocCONTENTSd_1290163195!mA. ` !X` !XOle $ArialTimes New RomanxXXrjVg(XXrdd'`$$*?IL)I 7+{c -&v} 7/9q 71Ll +7fLL@L#`OH7{c #7, +) . -+ 0 /- 2  1/ 8 $+7 622f&5YH "7xpxaexYG +?2sefe# `Sy^tG +Dx_xp_x,# `OzTG +;Enxae#`Cl{YG +?_2sef_#`Cl| xy} xz~ x{22f&#+`SOCl23  !    VjCD0100ChemDraw 8.0.3/hE1; 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrEPRINT 2`ObjInfo CONTENTS_1290158157 !mA. ` !X` !XlaB  EMF`,p  y eE  KRp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv%   &% 4+6 % &% (   f % ( '%  % ( % &% 6 % &% (   f % ( '%  % ( % &% 6  % &% (   f % ( '%  % ( % &%  6.  % &% (   f % ( '%  % ( % &% . 64+ % &% (   f % ( '% %  f%  % ( %  fRp"Arial M@MȻ::|X: ||||:|dv%  f TTXa֕@\@ fLPO? % &%  6 k % &% (   f % ( '%  % ( % &%  E6.  % &% (   f % ( '% F, CDIFVjCD0100ChemDraw 8.0.3/hE1; 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$/hE1;#B 7r<A 7Fj  7$ 2R aś7 +7Hų36{ų3;# `O              F4(DMHCGRTSxCW  x (XP`5"$D% $!"?XO `` " ! "ArialTimes New RomanFXJMDLSKXY Ariald 0 !% EE!% EE!% Qb(E.E!% 6EGE!% s<0EE!O% [BEE '  '  '  '  '  '  ' % ( % dd'`$$/hE1;#B 7r<A 7Fj  7$ 2R aś7 +7Hų36{ų3;# `O               VjCD0100ChemDraw 8.0.3(k" Y @@' :;<   `  3Ole EPRINT ?ObjInfoCONTENTS`li) EMF,p   l lKRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% 6 % &% (  : % ( '%  % ( % &% 6S7 % &% (  : % ( '%  % ( % &% S76 % &% (  : % ( '%  % ( % &% 6 % &% (  : % ( '%  % ( % &% 6 % &% (  : % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% %  % ( % Rp"Arial M@MȻ::|X: ||||:|dv%  TTEMظ@n@LPB8 S TTNQظ@n@SLPr % &% 6 % &% (  S % ( '% % %  % ( % %  TTgHpWظ@n@LPO? 0 TTqHyWظ@n@0LPHy8 % &% 6 % &% (  0 % ( '%  % ( % % % V0GN yyb y% % x6"x% % V,JK}!}!uu% %  % %  0 % '% % :%  % ( % :RpTimes New Roman HMx:1:|X:||||:|dv% : TT1Cظ@n@:LPNK : TT1Cظ@n@:LPa, : TT1Cظ@n@:LPHE % FteCDIFVjCD0100ChemDraw 8.0.3(k" Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$z(k"Mws 7yOEk 7{#QB 7}o5 nyu ryu #+7bYyy/y#`Bro5 +7[VMMM#`OH wy  y{  {}  }  w     } 2@2f&Y " +72@2f&#NaH !   FDMHCGRTS0FN  x (XP`5!z", oj a< 4 ] < NaHBrOH  W*% `` R B BX  `` >>jArialTimes New RomanFMDLSKXY Ariald 0!% `D`E!% VDq|E!% DE!% ,CDE!% ҵDdE!#Br% גDOD!O%b ,DE '  '  '  '  '  '  '  0! Na%b EE0 89d2 % % xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$z(k"Mws 7yOEk 7{#QB 7}o5 nyu ryu #+7bYyy/y#`Bro5 +7[VMMM#`OH wy  y{  {}  }  w     } 2@2f&Y " +72@2f&#NaH !    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Arial zlww 0w f-Arial ww 0w f- 2 Br!-%f%x1f%sCs%x      !"#$%&'()*+,-./0123456789:;<=>?@ABCFIJKLMNOPQRSVYZ[\]^_`cdefghijklmnopqrstuvwxyz{|}~%s%fx1%x%f%..k%01f%f01%=f 2 5Cl$ %**Q%*Q%.^%*%%rQ%r%rrQ%V%*Q%C 2 (O'2 OH%((n%9(n%K{% (%%pn9%p %ppn%s%9(n%n9%#Gn-%9[?--$M?WNM-%M?WNM%=T-$YTBOY-%YTBOY2  1. Mg, ether) 2 b2. H$ArialL /ww 0w f- 2 2- 2 bC=O#$' 2 3. H$- 2 3- 2 O'- 2 #+- 2 6 Arial ww 0w f-2 bconc. HBr, heat$!"System f &-- -' eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qi ''S ', Arial,Arial,Arial, ,uArial,Arial,Arial,Arial,Arial,Arial,Arial, $^ObjInfo')Ole10Nativem _1223038837:,eF!!X!!XOle D j #?fCC!#?fCC!#?ZCWC!#?ZCC!#?2KCC!#?2KCC!#?LCVC!#?~DC!#?"%DVC! ?v ?"~?"~n? '?v'?v ? ?: ?: '#?DwC!#?DC!#?֟DBC!#?֟DC!#?^&DwC!#?^&DC!#?IEAC!#?` ENvC!?a?x?xY?!}?!a}?*a*?5?y5j #?DuDD!#?DuDD!#?^DC!#?^D,D!#?GDD!#?GDD!#?*SDC!#?̑DD!#?JFDC! ?~?v?vv?{?~{?(~(?3?3?":D@DCC "DCDC DC@D@,DpD DDC@DCDC@DCAFT- 1. Mg, ether2. H2C=O3. H3O+ ~??@DC[DC/DC@DC[DC@DC[DCAFT[conc. HBr, heat eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qCompObj+-EhObjInfo.GOle10NativeH_12230388491eF!!X!!X''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ )?CZD!C)?CZD!C)?@DZD!C#? DCD!#?D'qD!#?[CZD!?k\k?kk??*(Q??)?k.k eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qOle TCompObj02UhObjInfo3WOle10NativeX>:''$',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^  )?@DTD!C)?DTD!C#?DTD!#?DTD!?ER R?RR?RsRgC x  2 --"System f, !T-.  Arial' +lww 0w f,-Arial{ Vww 0w f,-2 \C 2 \C 2 \x_1223297428$6eF!!X!!XOle aPRINT58b CompObjhC 2 C $2 H Arialm Mww 0w f,- 2 2 - 2 C $2 H - 2 3 - 2 \:C $2 \H - 2 t$3 -% xx% % jj%sx7x%2^%7b%%cxx-2 cC2 cgC 2 cC$2 cYH- 2 {}3- 2 cH$%b&%b&%bq&q%%-%3--$@3KB@-%@3KB@2 vkC2 vC2 v?C 2 tC$2 H- 2 23- 2 tC$2 H- 2 3- 2 vC$2 vH- 2 3- 2 vO'2 vH-%%%%:%wQ`x%wa%*f-%h-% r-$$u r^k$u-%$u r^k$u2 O1. NaNH$$$Arial www 0w f,- 2 2- 2 !  2 :O2. t 2 O3. 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