ࡱ> lY|#` bjbjmm .&:::8r,,[$Uhx pWc:(x+0[5 5 5 (Nd[$D 1. Acid/base reactions of alcohols and phenols. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  What is the practical advantage of using sodium hydride over butlyllithium to form alkoxides? c.  EMBED ChemDraw.Document.6.0  d.  EMBED ChemDraw.Document.6.0  2. Synthesis of silyl ethers and use of silyl protecting groups: a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  3. Reduction of carbonyl compounds.  EMBED ChemDraw.Document.6.0  4. Preparation of organometallic reagents: a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  d.  EMBED ChemDraw.Document.6.0  e.  EMBED ChemDraw.Document.6.0  5. Reactions of organometallic reagents. Assume acidic, aqueous workup for each reaction. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  d.  EMBED ChemDraw.Document.6.0  e.  EMBED ChemDraw.Document.6.0  f.  EMBED ChemDraw.Document.6.0  6. Short Syntheses. Write the final product after all reactions have been completed. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  d.  EMBED ChemDraw.Document.6.0      Chem 231 PS 10.1 Fall 2006 Dr. O. Alcohols; Silyl Ethers; Organometallics; Carbonyl Reduction page  PAGE 1 NAME _________________________________ due date _______________ 167UVX[_`~   - . / 0 7 8 V W X Y ǿ{sjk1hEoUj9WE hEoUVj&hEoUj$0G hEoUVjhEoUj#>5G hEoUVjhEoUj^&0G hEoUVjhnuUjKK hnuUVjhnuUhnuji&0G hEoUVjhEoUhEohnuhEoOJQJ+12YZ[ 1 2 3 Z [ \ ] ^ ^gdnu^dh        I J h i j k p        7 ǻనwojghEoUj]E hEoUVjhEoUj]E hEoUVjohEoUj]E hEoUVjWhEoUj]E hEoUVhEoCJOJQJ^J hEoCJjFhEoUjXE hEoUVhEojhEoUj;hEoUjmWE hEoUV+    ! 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QA TT<D,,K@8@QALPH8 % &% 6 % &% (  QA % ( '% % { %  % ( % { % {  TTlt,K@8@{ LPK8   TTu},K@8@ LPH8 % % % V0 i o i  % % m 6 % % V,Yo   o % %  % %    % '% FuCDIFVjCD0100ChemDraw 8.0m`@M?G ͌ @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$d'`{$$h|@M iN 7jN 7kN 7lN4 mN4 7nNՅ 7o +7n  M #`OHp ij q jk prr kl s lm rvtt mn u in ptv  lo wm` J#:#1xQ ' !+77 J#m` J#:#1#KHyè?Eè  "    |} h y wFxlDMHCGRTS$:,[  x ( `2 s "  !   Rj 8 8 tj N KHOH    C  ``  X X ArialFMDLSKXY Ariald 0!% E"D!% E"D!% P E"*D!% E"D!% E"D!% P EJD!O%b 8E D ' '(. ' '(. ' '(. ' 0!K%b Hf8E%D0  89d2% ( % CONTENTSp_1194337886!mA. pRcpRcOle 4ObjInfo5 `  fx# $$$$2ArialxXX$dg(XX$dd'`}$$h|@ԡ iN 7jN 7kN 7lN4 mN4 7nNՅ 7o +7n  ԡ #`OHp ij q jk prr kl s lm rvtt mn u in ptv  lo wk J#u#1xQ ' !+77 J#k J#u#1#KHyè?Eè  "    ~ h y wVjCD0100ChemDraw 8.0^} 4  @@' :;<  CONTENTS6d_1194671651!mA. pRcpRcOle PEPRINT<- `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`$$R^}3S22_ 7Ueea 7Vk Wy !7X33T #Y33 %+73333#`OHhy '7_ UV `  SV a "VW b $WX c &XY i (Xh l,k2q )7ev?xB2?x ev 2e evԇ 2B +B BB#`Li    ,#BuLim` *     R m l VjCD0100ChemDraw 8.0YVI ks 33 @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$dd'lg)f EMF-6    R>KRp"ArialK$Kh#`$K4w`$Kͫ`$K82|88@0@I |8||| 4P|14P,8XKXp8<||||8|dv%   Rp8"Arialx8x8x/ 8dv||||x8|84[0X <0h80X0x8X8|L||||8|dv% c% cRp"Arial P@4P8 38|X8 ||||8|dv% c TT  @j?@cLPC8  TT  @j?@LPH8 % Rpj"Arial|ex8He<`UUUU%o@b@Mr@|b@x8`UUUU%o@ @j?@LPHH8 % &% u6au % &% (   % ( '% &% 6a  % ( '% ( % D%  % ( % D% D TTPX @j?@DLPCO8  TTYa @j?@LPH78 % % %  TTc h @j?@LP2N& % % &% 6: % &% (   % ( '% % *%  % ( % *% * TTu @j?@*LPMrE p TT @j?@pLPg\,  TT @j?@LPBC8  TT @j?@LPrO % &% 6# % &% (   % ( '%  % ( % % % V0  v  v i v% %  v6t v% % V,M   ys ys t t% %  % %   % '% % u%  % ( % u% u TT @j?@uLPCe8  TT @j?@LPH.8 % % %  TT  @j?@LP3& % % % j% j% j TT @j?@jLPC8  TT  @j?@LPH8 % % %  TT   @j?@LP2& % % &% 6` % &% (   % ( '% % _ %  % ( % _ % _  TT!* @j?@_ LPO?   TT+3 @j?@ LPH8 % &%  6V  % &% (    % ( '% % %  % ( % Rp"Arial7wZw 0w4w1w PH4P8`08|X8||||8|dv%  TT @j?@LP+8 % FXICDIFVjCD0100ChemDraw 8.0YVI ks 33 @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$d'`$$ndfVI qLX +713[dfVIܽ[#`CH2rLs +713Rwdf2h}Rw#`CHsg +7g2g g#`CH2te3Ԣ !7DXɕ 5n  +Mn,DF5n,#`Mgb܍ #+I q I #`Brb    ˌ3S3e#`MgBrx qry  rs z "st 0sef.Ye $+7?e0seʑe#`CH3̌ %+72seo#`CH2f# '+7f1fُf.#`OH &  ( Yff )5This label has conflicting or unassignable charges. +"wq"fA #     n FDMHCGRTS$(g  x ( `2  # $ h% '   s !&( " CH3 CH2OH CH2 CH CH2MgBr ``  0W  cW ``  4 0 g ``  5} } < ``  /.  b. ``  / R 2 5 R ``  5 ; h  ``  6 e e `C   ) V Ge+ArialFMDLSKXY Ariald 0 +2XC?Arialx+ 0!%b ~T^DD!%b ?DD!%b 9DD!MgBr! Mg% DaìD!#Br% SqDaD! _D`D ' '"4MgBr6=  @DD< '( ' ' 0!%b E/D!%b D+EoD!O%b \6ED ' '0 nZ Z89d2% % ObjInfoQCONTENTSRD_1194337302/!mA. pRcpRcOle t`$$ndfVI qLX +713[dfVIܽ[#`CH2rLs +713Rwdf2h}Rw#`CHsg +7g2g g#`CH2te3Ԣ 7DXɕ 5n  +Mn,DF5n,#`Mgb܍ #+I q I #`Brb       ˌ3S3e#`MgBrx qry rs z st 0sef.Ye +7?e0seʑe#`CH3̌  +72seo#`CH2f# "+7f1fُf.#`OH !  # Yff $5This label has conflicting or unassignable charges. +"wq"fA      n VjCD0100ChemDraw 8.0eeC3ӦP 4  @@' :;<  ObjInfouCONTENTSvO_1163388729!mA. pRcpRcOle  `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`Q$$[Y,@ +7f&TYTq# `C@  +7f&a Ya q/An atom in this label has an invalid valence.# `C@ "+7f&Y,#`CH3 !  # ZeeC3Ӧ3| '7r (| )7 * /733T 1733 3+7y3̬33Ӧ3#`OHd 57fFf\ 77ǨlK 9+72s̄LeeCݽ̄L#`Cl +  ,  -  .  0  2  4  6  8 L :K @33@ %5This label has conflicting or unassignable charges. +@@ $  N. &    RS Z[ VjCD0100ChemDraw 8.0e0! gfgf @@' :;<   `  fx# $$$$2Arialx  f g'  fdd'ObjInfoCONTENTS_1163388781_ !mA. pRcpRcOle `0$$ e0Js e0Js ͲF *7 @M +ͲZ8 ,7@1 -7Z8 .7F /7@@\ 07̲2h 1+72JdeJd Js#`OH #    $   %  &  '  (   )   2  T5̬!2Sf&  571ۛ1!g%fF +W!f^f^!2+# `O&Ae +(eB A[1!eB #`CH'Ag (ۛ3s )ۛ * %&+ %', '(- (). &) T5̬!2S/An atom in this label has an invalid valence.#THF~3~wfL 3/An atom in this label has an invalid valence. TMS-Cl3fƬ 4&ChemDraw can't interpret this label.imidazole!`} 6    23     !ObjInfo!CONTENTSI _1163396779$!mA. pRcpRcOle VjCD0100ChemDraw 8.02p'!B gfgf @@' :;<   `  fx# $$$$2Arialx  f g'  fdd'`S$$" p'%d# p'%d$Z&@ 17%&L 27&&3 37'Z@' 47(Z Y 5+7f@%Us%U%d#`OH) -$% * .$& )++ /&' , 0%( -T̬!B2S.f   A7TB2p\g00XfF 6+W\f^JTf^p\2+# `O1Oe 7+SeBAK22\eB#`CH2Og 83B3s 94B :5 ;016 <027 =238 >349 ?14̌T̬!B2S/An atom in this label has an invalid valence.#THF>2zv?=~ C7U?3ƬC +ff̶̶e#`SiDfl E F3 Gf&fl  HƬ !Ifl "Jf& #+ z?zwW2#`ClK $CDL %CEM &CFN 'DGO (DHP )DIQ *CJz2zv?#TBDMSCl;|33|fƦ @&ChemDraw can't interpret this label.imidazole<`w B    VW " - < > VjCD0100ChemDraw 8.0A"KvgQ o ͌ @@' :;<   `  fx# $$$$2EPRINT#%mTCObjInfo&CONTENTS _1163775455C)!mA. pRcpRcuXl7B  EMFTC;   ;C Nb KRp8"Arialf  ?wxw:w||84`[n|Pd4P X0oOP? |twxw:w||dv%   &%  6\  % &% (    % ( '%  % ( % &% \ 6N  % &% (    % ( '%  % ( % &% N 6  % &% (    % ( '%  % ( % &%  6  % &% (    % ( '%  % ( % &%  6w  % &% (    % ( '%  % ( % &% w 6N  % &% (    % ( '% % n %  % ( % n Rp"Arial%ww:wP4P X0oDwx%X?wxw:w||dv% n  TTr{,@Z@n LPO? Wn  TT|,@Z@Wn LPH8 % &% N 6 N  % &% (  Wn  % ( '%  % ( % &% \ 6  % &% (  Wn  % ( '% % _ %  % ( % _ % _  TT @Z@_ LPC8   TT @Z@ LPl % &%  6  % &% (    % ( '% % _ %  % ( % _ % _  TT@Z@_ LP1,   TT@Z@ LP)   TT@Z@ LP    TT@Z@ LPT,   TT@Z@ LPB8 *  TT@Z@* LPD8 f  TT@Z@f LPME   TT@Z@ LPS8   TT@Z@ LP-   TT@Z@ LPC8 ;  TT@Z@; LPl N  TT@Z@N LP  e  TT@Z@e LP/ |  TT@Z@| LP    TT@Z@ LPi   TT @Z@ LPmE   TT@Z@ LPi   TT@Z@ LPd, ,  TT@Z@, LPa, Z  TT &@Z@Z LPz,   TT'-@Z@ LPo,   TT.0@Z@ LPl   TT17@Z@ LPe, % % gk % gk % gk  TT,@Z@gk LP2, k  TT,@Z@k LP) % %  b %  b %  b  TT*@Z@ b LPC8 % % _ b % _ b % _ b  TT*@Z@_ b LPC8 % &%  ( 6U (  % &% (  _ b  % ( '% &%  A 6U A  _ b  % ( '% ( &%  [ 6U [  _ b  % ( '% ( % b %  % ( % b % b  TT*@Z@b LPC8 3 b  TT*@Z@3 b LPH8 % Rpj"Arial??Hf@P/@"@ ?wxw:w||4P|4P, X0oTx$>8wxw:w||dv% o t Rp"ArialZZ!^K %ېxP4>P0o? Pb@ lP4Pd X0o? ?pb@wxw:w||dv% o t  TT!-@Z@o t LP3& % % &%  A 6 A  % &% (  o t  % ( '%  % ( % &% % *   b %  ? 6 ? % % V0 ] + 1 + ] % % % ( / 6` % % V,1 _ _ 1 % %  % %   ?  &% '% % ( % % % % % % e %  % ( % e % e  TT0?@Z@e LP3,   TT0?@Z@ LP)   TT0?@Z@ LP    TT0?@Z@ LP    TT0?@Z@ LPB8   TT0?@Z@ LPu, % % % % C % C  TT6B@Z@C LP4& % % % f % f  TT0?@Z@f LPN8 % % % %  %   TT.:@Z@ LP+& % % %  %   TT0?@Z@ LP    TT0?@Z@ LPF2 % % % %  %   TT.:@Z@ LP- % % F(  CDIFVjCD0100ChemDraw 8.0A"KvgQ o ͌ @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$d'`L$$Zv&K@fݍ(f 7ݍ2f  ݍ<f !7ݍ2f "ݍ2f '7ݍ<fg )7ݍ<f ++7Ct@fv8f@f#`OHݍ2f -7ݍ*f /+7Ct.fv&K.f#`Cl #  $  %  &  (  *  ,  .  0 ?v'7fZ~AE@ ;f1 3+7C>f-v'7f->?4# `CA ;f'B 4+7C>f>v'7f>>?E/An atom in this label has an invalid valence.# `CB ;f# 6+7C>f%v'7fZ~Af%#`CH3C 5@A D 7@B E *fA"f, o 1Parentheses don't match.#1) TBDMS-Cl / imidazoleF @fA8fB  2Parentheses don't match.2)JNf EfvgQ7 :Parentheses don't match.J @  @3) Bu4N+ F-G ;fN EfN 8  H 1f] 1f 9    MN Z H ?F<0DMHCGRTSP%]e  x ( `2e8F93+46+   !k"'H)P+ -S $/57#$%&(* , . 0 CC CH3 OH Cl `` O `` Os `` O ``  m- ``  9 } 9  I1{1) TBDMS-Cl / imidazole  *2e%32) >   @@    @@ (%:e \Z 3) Bu4N+ F-ArialFMDLSKXY Ariald 0 V V XokAriald1) TBDMS-Cl / imidazole 0  2 n XEAAriald2) 0  - . X ArialdArialdArialdArialdArialdAriald3) Bu4N+ F- 0!% ADX9E!% D?E!% ADEE!% D?E!% AD?E!% @EEE!O%b EEE!% AD?E!Cl% AD:E ' ' ' ' ' ' ' ' ' 0!% >EDE!% XIEDE!%b 5EDE '( ' 0 N C?Ariald-0 89d2% %       !"#$%&'()*+,-./0123456789:;<=>?CDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopquvwxyz{|}~ArialxXX$dg(XX$dd'`N$$Zv&K@fݍ(f 7ݍ2f  ݍ<f !7ݍ2f "ݍ2f '7ݍ<fg )7ݍ<f ++7Ct@fv8f@f#`OHݍ2f -7ݍ*f /+7Ct.fv&K.f#`Cl #  $  %  &  (  *  ,  .  0 ?v'7fZ~AE@ ;f1 3+7C>f-v'7f->?4# `CA ;f'B 4+7C>f>v'7f>>?E/An atom in this label has an invalid valence.# `CB ;f# 6+7C>f%v'7fZ~Af%#`CH3C 5@A D 7@B E *fA"f, o 1Parentheses don't match.#1) TBDMS-Cl / imidazoleF @fA8fB  2Parentheses don't match.2)JNf EfvgQ7 :Parentheses don't match.J @  @3) Bu4N+ F-G ;fN EfN 8  H 1f] 1f 9    OP Z H ?Ole ObjInfo(*CONTENTSx_1163776386c-!mA. pRcpmUcVjCD0100ChemDraw 8.0ȍ&5r.ً @  @@' :;<   `   L|;X x# $$$$2Arialx,, 8 ` g(,, 8 `dd'`$$hȍ^"iȍ^"j  `k6 al+ b7m c7n d7o e7p+ f7qn g+7#__# `Or h+7bȍb"# `Hs Wjk t Xjl u Ylm v Zmn w [no x \op y ]jp z ^kq{ _kr ? f0? f0w  wC% xȫ y7) z7& {7) |7ȫ }7{ ~+7-&?,# `O, 7w](n\+E! 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N2fƚyr ϖn's,]9cM^PDp(Ӷ@:Fs ^y$[JCօxFP"nsyk{G<%y :UyyMY)-nN3u`Y7~?ZzsksnziIFY8zJz`Ciw>{&{j0F釛~Ole ObjInfo@BCONTENTS_1163775616?GE!mA. pmUcpmUc< @  @@' :;<   `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`<$$da}̗V-e $7W-j} %7X w~ &7Y-zM '7Z o (`-u .b-m 07dē{ 2+7*z˥]w˥̗# `O[ )VW \ *WX ] +XY ^ ,YZ _ -VZ a /Z` c 1`b e 3`d f 4bd ĺ[!\zo/hēe 57i-o 67j-o 77kēeM 8l\ 97m\ :7tēe A#+7*zi/a/*zi/#`Brn ;hi soo <ij p =jk ouqq >kl r ?lm qss @hm u Bkt w-`{k?0 C&ChemDraw can't interpret this label.2 Mg, Et2O, - 10 Cx-u:-u D    =>  x Ole @ObjInfoDFACONTENTSB _1163775630I!mA. pmUcpmUcVjCD0100ChemDraw 8.0]Gf};ŸJ @  @@' :;<   `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`N$$ vGfBvGfB: F7ĭ& G H7ĭ I7Oƥ$"/K<  +ƥ+#`Mg=aW  #+ʴOʴ#`Br@b$|   A  @<>  <=*\\ĭfB#`MgBr C  D  E ]Gf}y-} 27z-} 37{ĭ3 47|- 501}- 601~ĭ3 77- >+7*˚]G˚m̗# `O- A+7*]G՞#`CH3 8yz  9z{  :{|  ;|}  <}~  =y~  ?|  @}  B} .KVsf3-]G" M7PrdތgCfyz %+fvQfvތ2^~# `ODm/en &+eurI|d`eur#`CHEm/g 'Fr3 (GrLs )H *CDI +CEJ ,EFK -FGL .DG-KVsf3/An atom in this label has an invalid valence.#THF-`s;Ÿ8 J5This label has conflicting or unassignable charges.- 25 C-`m L5This label has conflicting or unassignable charges. +-H- K    QR    .VjCD0100ChemDraw 8.0]z?};J @  @@' :;<   `  fx# $$$$2Ole rObjInfoHJsCONTENTSt _1163775642'M!mA. pWcpWcArialx,, 8 ` g(,, 8 `dd'`K$$ ]z?}S3]z?}S3ĺ & '7& (7ĺ} )7` *+7*G]zĠ̊# `O "  #  $  %0`n/]GK .7L<*<- =- +*<*#`Li> <=-`n#`CH3Li2KVsf31]G" /7Mrdތg@fyz +fvQfvތ2^~# `OAm/en +eurI|d`eur#`CHBm/g Cr3 DrLs E @AF @BG BCH CDI AD-KVsf3/An atom in this label has an invalid valence.#THF-`m +5This label has conflicting or unassignable charges. +-`s;8 ,5This label has conflicting or unassignable charges.- 78 C-H- -    NO  0  2VjCD0100ChemDraw 8.0]Y}* r @  @@' :;<   `  fx# $$$$2ArialxOle ObjInfoLNCONTENTS\ _1163775655Q!mA. pWcpWc,, 8 ` g(,, 8 `dd'`N$$ ]Y}* ]Y}* -s B-٨ CĺM D7ĺ E7-} F7Ġ G7ĠM H7ĺ I+7*1]1# `O-f J+7* Ϊ<Ϊ* 3# `H :  ;  <  =  >  ?  @  A K ĺ!\zfuē L7- M7- N7ēM O P7 Q7ē  X7OMs<&  +&!#`Mg= M #+YMMYM#`Br@ )\   A !@<> "<=*zēfu#`MgBr R  S  T  U  V  W  Y 4KVsGf[3]GJ ]7PrdތgCfyz -+fvQfvތ2^~# `ODm/en .+eurI|d`eur#`CHEm/g /Fr3 0GrLs 1H 2CDI 3CEJ 4EFK 5FGL 6DG-GKVsGf[/An atom in this label has an invalid valence.#THF-`m Z5This label has conflicting or unassignable charges. +-A`sA;` [5This label has conflicting or unassignable charges.- 78 C-p-B \    QR    4VjCD0100ChemDraw 8.0]"Y}`D @  @@' :;<   `  fx# $$$$2ArialxOle ObjInfoPRCONTENTS _1163775666O+U!mA. pWcpWc,, 8 ` g(,, 8 `dd'`P$$ ]"Y}`Dj"]"Y}`Dj-3s 6-3٨ 7ĺ&M 87ĺ& 97-3} :7Ġ? ;7Ġ?M <7ĺ& =+7**1]"1*# `O->f >7IJ=<̄A+  +2kE+e=+EƧ# `O=HO >̄A BHt  C B<? <=@ =>*B~]G:~`Dj#`OCH2CH3 .  /  0  1  2  3  4  5 ? 6KV&su/f5]G*x D7RrdތgEfyz  +fvQfvތ2^~ `OFm/en !+eurI|d`eur#`CHGm/g "Hr3 #IrLs $J %EFK &EGL 'GHM (HIN )FI-.uKV&su/f/An atom in this label has an invalid valence.#THF-4`,sn63] @&ChemDraw can't interpret this label.)`2 equiv. CH3CH2MgBr-3`+m5 A5This label has conflicting or unassignable charges. +-<o`4so;= B5This label has conflicting or unassignable charges.- 78 C-1-1p C    ST    6Ole ObjInfoTVCONTENTS _1163776893Y!mA. pWcpWc      !"#$%&'+,-./0123456789:;<=>?@ABCDEFGHIJKLMQRSTUVWXYZ[\]^_`abcdefghijnopqrstuvwxyz{|}~VjCD0100ChemDraw 8.0]GTY{;v^ @  @@' :;<   `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`F$$κbp*.nM,κbp*.nMGj <7c& =7c@ >7Gj ?7Gj @+7*.nVf*.nM#`Li 8  9  :  ; +]GTY{Mv̗-f *ēr +7`vs ,7`l -7zbs .ĭ] 4+7*a]YY{d#`CH3-X 6+7*\ˣ]GTˣm\̗# `O /  0  1  2  3  5  78`Z>`dT7]G^7B D7G*a0mvN<h =*a+) >hvN  ?*a^B !@h5 "+]l2 e20me9# `OA #<=B $=@C %>?D &?@-b>`Z>`dT#`Et2O-h``mj A5This label has conflicting or unassignable charges. +-u>`ms>;v] C5This label has conflicting or unassignable charges.- 50 C-h\-h= B    HI +  8Ole (ObjInfoXZ)CONTENTS*_1163775355]!mA. pWcpWcVjCD0100ChemDraw 8.0ܭg3! @  @@' :;<   `  fx# $$$$2Arialx,, 8 ` g(,, 8 `dd'`$$ܭg3!҉eܭg3!҉ewe 0wK 1kme 27kmr 37w 4^r 57^e 67wK 7  97W{VG $+$W{# `O %B &  ' (T##!҉e#`OCH3k%  ;+7To=g=oe # `O ^ =+7TEx~e# `Ok ?+7To3ܭg3Tof# `H )  *  +  ,  -  .  /  8  :  <! > # @ &8rfX.!ljfX.t! 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Synthesis of Alcohols: Title  FMicrosoft Office Word Document MSWordDocWord.Document.89q@@@ NormalCJ_HaJmH sH tH DA@D Default Paragraph FontVi@V  Table Normal :V 44 la (k@(No List 8O8 LecNotes CJOJQJ4@4 Header  !>O> problemSets CJOJQJ4 @"4 Footer  !.)@1. Page Number&12YZ[  123Z[\]^!FGHIlmnop;<=de=>?;<=>?@Aghijklmn@00000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000h00U00h00U00h00U00h00U00@0@0@0@0h0000t12YZ[0 0000000(A*1*bb00V000000  7   ;   6UW_~-/7VXIhj79A`b9;Dcen79Dcer::::::::::::::::::::::::ry{!_ot23[\_  34=>@AjkABno33333333333333333333333#06XZ07Y]]^_ $.EFHlnpq;<df5?_u(Eonuq@Q@UnknownGz Times New Roman5Symbol3& z ArialCFComic Sans MS"1hff[fD?D?!842QHX ?q2Synthesis of Alcohols: tom olmsteadGCCCD