ࡱ> ') &lyp%` bjbj"x"x 4:@@ JJJJJJJ^----D-T^9*.0000111P9R9R9R9R9R9R9$:h+=v9J11111v9JJ0093331"J0J0P931P933:7,JJP80. -SY-!2j7 89097R=2=P8=JP8|11311111v9v93 11191111^^^^^^^^^JJJJJJ Problem Set 4 for Exam 4 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  Draw the structure of the following alcohols: i) 3-methyl-2-buten-1-ol ii) cis-1,3-cyclohexanediol Which of the following compounds is more water-solubility? Explain why.  EMBED ACD.ChemSketch.20  or  EMBED ACD.ChemSketch.20  Which of the following compounds has the higher boiling point? Explain why.  EMBED ACD.ChemSketch.20 or EMBED ACD.ChemSketch.20   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  Write arrow-pushing mechanisms for each of the following reactions. a.  EMBED ACD.ChemSketch.20  b.  EMBED ChemDraw.Document.6.0  c)  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 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  b.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  c.  EMBED ACD.ChemSketch.20   EMBED ACD.ChemSketch.20  d.  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. Feel free to draw an incomplete routewe will give you partial credit where I can  EMBED ChemDraw.Document.6.0  + , S T V W ˱zvokgvc[cPH[c[jKh"AUjFJ h"AUVjh"AUh"Ah}hK hxphcghxphxpOJQJ^JaJmHsHhcgOJQJ^JaJmHsHhqmHsHhcghcgmHsHhcghqj=5L hqUVhcghqmHsHjhqU hcghcgCJOJQJ^JaJhcgCJOJQJ^JaJh"ACJOJQJ^JaJ+ , T U V W gdxp & Fgd"Agds &#$/gdq & F7$8$H$gd"A h7$8$H$^hgd"A$h7$8$H$^ha$gd"A 5 6 U X w $Ifgd/  & Fgd"Agd"A 6 7 Q R S T X Y s t u v y |   5 6 7 8 = > X Y Z [ _ ` z { | } xpjh"AUjH h"AUVjdh"AUjH h"AUVj>h"AUj|H h"AUV h"A5\ hxphxpj4h"AUjJ h"AUVj h"AUjGJ h"AUVh}jh"AUj h"AUjFJ h"AUVh"A,w x y z { | } ~ mdddd[[ $Ifgd/ $Ifgd}kdj$$IfTlFO t06    44 layt}T~  mhcccccc[ & Fgd"Agdsgd"Akd$$IfTlFO t06    44 layt}T           < = > ?  & Fgd"Agdsgd"Ah^hgd"A}      8 9 : ; < = ? 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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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SYSYl$J" EMF&,p  C )M  KRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &%  6 l % &% (    % ( '%  % ( % &% k6  % &% (    % ( '%  % ( % &%  6k % &% (    % ( '%  % ( % &% pk6  % &% (    % ( '%  % ( % &% k6f % &% (    % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% (%  % ( % (Rp"Arial M@MȻ::|X: ||||:|dv% ( TT2Ǖ@Mv@(LPO? i TT2Ǖ@Mv@iLPH8 % &% pk6  % &% (  i % ( '%  % ( % % % V0$ 6 K 6  6% %  56)5% % V, :(:(2 2% %  % %  i % '% % Z %  % ( % Z RpTimes New Roman HMx:1:|X:||||:|dv% Z  TT2Ǖ@Mv@Z LPT8   TT2Ǖ@Mv@ LPs&   TT2Ǖ@Mv@ LPCeE   TT2Ǖ@Mv@ LPl % % l% l% l TT02Ǖ@Mv@lLPP8  TT02Ǖ@Mv@LPy,  TT02Ǖ@Mv@LPr  TT02Ǖ@Mv@LPi   TT02Ǖ@Mv@ LPd2 E  TT02Ǖ@Mv@E LPi a  TT 02Ǖ@Mv@a LPnee,   TT02Ǖ@Mv@ LPe, % F CDIFVjCD0100ChemDraw 8.0.32O]3@9 Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$a O]3b3P] @7c3cw A7d3v֑ Ce3ѫ E7f3 G7g3v֑ I7h3 K+7ٯ 33#`OHi Bcb j Ddc k Fed l Hfe m Jdg n Lfh r2@ݝq@ N7Y|x?: *yD+ +zD  ,{? -|;  .};+ /~? 0?X 1+e&}UY}UL#\# `S?X 2+e&TYTe\# `O?X 3+e&TYTe\# `O?v 4+e&AsYAsL|#`Cl 5xy  6yz 7z{  8{| 9|}  :x} ;{~ <x = > ??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 ' (.  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Dd /0  # A" +o!1lXb }9 @=Z +o!1lXH$'^ ( x lqgC >@:8+`lv ]|">l8"U)D>M?DE)B(*i-T LBיowg~Vz>3of̼;[`=lV XS <nY:CwuHq6[*=>9Orr!p–)iW.t `9(H^9@}}x,Ӧ%ObWB0_ɐde?,Vh3jQT:PUCSv#2EO&dvP !=; @ #?= B %A? D '=C J )AI N2@ f&MY +7lBF"xv +{{5e"# `Pyv  +c cBF"# `Czv  +l lB# `C{ xy| xz 2@ f&/An atom in this label has an invalid valence.#PCCK, *   FxDMHCGRTSGUT  x (XP`5cc*~+d d "$ &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 % %  VjCD0100ChemDraw 8.0.3S2/ Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`CONTENTS_1290157944!mA. SYSYOle EPRINT       !%&'()*+,-./0123456789=>?@ABCDEFGHIJKLMNQTUVWXYZ[\]^_`adghijklmnopqrsvyz{|}~~$$:S2`9T 7;m 7=& ?9 7AL 7C2& !7I` #+7f``@ `#`OH< ;9 > =; @ ?= B  A? D "=C J $AI N2@ f&MY &7lBF"xv +{{5e"# `Pyv  +c cBF"# `Czv  +l lB `C{ xy| xz 2@ f&/An atom in this label has an invalid valence.#PCCK, %    VjCD0100ChemDraw 8.0.32?I@  Y @@' :;<  lWF EMF ,p  v2 Y QjKRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% =6d % &% (   % ( '%  % ( % &% 6= % &% (   % ( '%  % ( % &% 6 % &% (   % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% 5%  % ( % 5Rp"Arial M@MȻ::|X: ||||:|dv% 5 TT""@×@5LPO? 5 TT""@×@5LPHM8 % &% ,6 % &% (  5 % ( '%  % ( % % % V0Q)\Q% % Z6% % V,\\% %  % %  5 % '% % %  % ( % RpTimes New Roman HMx:1:|X:||||:|dv%  TT"@×@LPS8 & TT"@×@&LPOK o TT"@×@oLPCE  TT"@×@LPl) % RpLTimes New Roman|8|2|||$h|2||| FpHn"0: XMx:0U:Xf:Hn$||||:|dv% RpTimes New Romanw!-(wMw:w!-!rZ(|xHMLM\: δMf@(P (Mx:P4X:f@||||:|dv%  TT"@×@LP2& % % &% =6= % &% (   % ( '% FCDIFVjCD0100ChemDraw 8.0.32?I@  Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$*?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 % ( % ObjInfoCONTENTS_1290158157!mA. SYSYOle " `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrdd'`$$*?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(k" Y @@' :;<   `  3xx# $$$$2EPRINTObjInfo#CONTENTS$`_1290163707=!mA. SYSYli) EMF,p   l lKRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% 6 % &% (  : % ( '%  % ( % &% 6S7 % &% (  : % ( '%  % ( % &% S76 % &% (  : % ( '%  % ( % &% 6 % &% (  : % ( '%  % ( % &% 6 % &% (  : % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% %  % ( % Rp"Arial M@MȻ::|X: ||||:|dv%  TTEMظ@n@LPB8 S TTNQظ@n@SLPr % &% 6 % &% (  S % ( '% % %  % ( % %  TTgHpWظ@n@LPO? 0 TTqHyWظ@n@0LPHy8 % &% 6 % &% (  0 % ( '%  % ( % % % V0GN yyb y% % x6"x% % V,JK}!}!uu% %  % %  0 % '% % :%  % ( % :RpTimes New Roman HMx:1:|X:||||:|dv% : TT1Cظ@n@:LPNK : TT1Cظ@n@:LPa, : TT1Cظ@n@:LPHE % FteCDIFVjCD0100ChemDraw 8.0.3(k" Y @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$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 % % $ArialTimes New RomanxXXrjVg(XXrdd'`$$z(k"Mws 7yOEk 7{#QB 7}o5 nyu ryu #+7bYyy/y#`Bro5 +7[VMMM#`OH wy  y{  {}  }  w     } 2@2f&Y " +72@2f&#NaH !    VjCD0100ChemDraw 8.0.39}%4Zm 4g @@' :;<   `  3xx# $$$$2Ole :EPRINT$ObjInfo;CONTENTS<lG EMF$,p   J |KRpTimes New Roman|8|| :,|||||:|pp`  |HMx:QX:|||||:|dv%   &% 76f % &% (  ) % ( '% Rp8"Arialp_P :||||:|R DMM<Ȼ:X:L|||||:|dv% %  % ( % Rp"Arial M@MȻ::|X: ||||:|dv%  TT.7@*@LPOee? % &% f6` % &% (   % ( '%  % ( % &% `6 % &% (   % ( '%  % ( % &% 6f % &% (   % ( '%  % ( % % % V0 '\q\F\% % \6\% % V,c#$``XX% %  % %   % '% % %  % ( % RpTimes New Roman HMx:1:|X:||||:|dv%  TT\c@*@LP12  TTdh@*@LP)!@ 5 TTjm@*@5LP  N TTnr@*@NLP( o TTs}@*@oLPCE  TT~@*@LPHE % RpLTimes New Roman|8|2|||$h|2||| FpHn"0: XMx:0U:Xf:Hn$||||:|dv% RpTimes New Romanw!-(wMw:w!-!rZ(|xHMLM\: δMf@(P (Mx:P4X:f@||||:|dv%  TT @*@LP3& % %  %   TT@*@ LP) % % A% A TT @*@ALP2& % % g% g TT@*@gLPCE  TT@*@LPu ,  TT@*@LPL8  TT@*@LPi % % % %  TTb-i?@*@LP22 9 TTj-n?@*@9LP) [ TTp-s?@*@[LP  t TTt-~?@*@tLPHE % %  %   TT3A@*@ LP3& % % %  TT-?@*@LPOK % % )% ) TT*8@*@)LP+, % % FCDIFVjCD0100ChemDraw 8.0.39}%4Zm 4g @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrd'`$$9}%4ZmGhm4  7kWI kWg 7X=X +7AT9TXB`\# `O        F@w3s=@w̌I Parentheses don't match.`1) (CH3)2CuLid{Y{̌g Parentheses don't match.`2) H3O+RR|    FDMHCGRTS4  x (XP`5.wj.w 0 ..,O `` -",-)< `` - Q, Q- 1) (CH3)2CuLi `` / . 0 2) H3O+ArialTimes New RomanF MDLSKXY Ariald 0 fqX[W Times New Roman x1) (CH3)2CuLi 0 zh XOKTimes New Roman x2) H3O+ 0!% @DE!% rH8DnE!% 9DnE!O% r]D|PE '  '  '  ' 0 5;;89d2 % % $ArialTimes New RomanxXXrjVg(XXrdd'`$$9}%4ZmGhm4  7kWI kWg 7X=X +7AT9TXB`\# `O        F@w3s=@w̌I Parentheses don't match.`1) (CH3)2CuLid{Y{̌g Parentheses don't match.`2) H3O+RR|    _1223038721LteFSYSYOle OCompObjPhObjInfoR eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ j #?Ole10NativeS_1223038735eFSYSYOle bCompObjchfCC!#?fCD!#?ZCC!#?ZC@D!#?wCC!#?wCD!#?T&DC!#?~DC!#?" 6DC! ??d?dI? i}? iQ??!}?|!}?| eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qX''B',Arial,Arial,Arial,Arial,AriObjInfoeOle10Nativef\_1223038837eFSYSYOle tal,Arial,Arial, $^ '#?9DC!#?9D D!#?ֿDC!#?ֿDD!#?^FDC!#?^FD D!#?*DC!#?,DC!?*2*?%?_%*?r?r2g?{2{?*? eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qCompObjuhObjInfowOle10Nativex_1223038849eFSYSY''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ )?CZD!C)?CZD!C)?@DZD!C#? DCD!#?D'qD!#?[CZD!?k\k?kk??*(Q??)?k.k eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qOle CompObjhObjInfoOle10Native>:''$',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^  )?@DTD!C)?DTD!C#?DTD!#?DTD!?ER R?RR?RsR eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209q''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $_1223039407 eFSYSYOle CompObjhObjInfoOle10Native_1223039419eFSYSYOle CompObjh^ j #?CTD!#?DyD!#?uCD!#?6DYD!#? DD!#?%6DDD!#?9J$DSD!#?D D!#?D`D! ? ?o ?t ?Spo?Spt ?t ?Sp~?t t?Sp eFACD/ChemSketchACD/ChemSketchACD.ChemSketch.209qObjInfoOle10Native_1290160178!mA. SYSYOle ''',Arial,Arial,Arial,Arial,Arial,Arial,Arial, $^ #?姞DtD!#?aDyD!#?DDD!#?DyD!#?DD!#?ŷDS̻D!#?DdD!?K$?$?$K??$?? $ VjCD0100ChemDraw 8.0.3:_Y͓MEPRINTObjInfoCONTENTS_1290160211!mA. SY-SYlY EMFp,p  !  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