ࡱ>  lbjbj .&8M<$)s(vvvA)C)C)C)C)C)C)$l+.^g)vvvvvg)|)vA)vA)'h(N 0($ (-))0)(l.L2l. (l.(Pvvvvvvvg)g)~vvv)vvvvl.vvvvvvvvv : 1. Draw the expected SN2 product. Write N.R. (no rxn) if none is expected. Shown here is the structure of three good leaving groups:  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  g.  EMBED ChemDraw.Document.6.0  h.  EMBED ChemDraw.Document.6.0  i.  EMBED ChemDraw.Document.6.0  j.  EMBED ChemDraw.Document.6.0  2. Draw the expected SN1 product(s). Recall that nucleophilic solvents may compete for the substrate; if more than one product is expected, circle the major product. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  d.  EMBED ChemDraw.Document.6.0  3. Observe the reaction mechansim (SN1 or SN2) then indicate the stereochemistry of the product; there may be more than one stereoisomer. a. SN2  EMBED ChemDraw.Document.6.0  b. SN1  EMBED ChemDraw.Document.6.0  c. SN1 EMBED ChemDraw.Document.6.0  d. SN2  EMBED ChemDraw.Document.6.0  e, SN2 EMBED ChemDraw.Document.6.0  f. SN1 EMBED ChemDraw.Document.6.0  4. So far, you have examined intermolecular SN2 (bimolecular process). Now, draw the cyclized product from an intramolecular SN2 reaction (unimolecular process). To get started, recall what is formed when an alcohol or carboxylic acid is treated with a hydride reagent. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0      Chem 231 PS 6.1  DATE \@ "M/d/yyyy" 8/17/2009 SN2 SN1 Reactions page  PAGE 1 NAME _________________________________ due date _______________ Lmoq   㹱砓ndWMjMhSQU^JjHSoG hSQUV^JjhSQU^J!jfDhaVhSQCJ0U^JaJ0'j SoG haVhSQCJ0UV^JaJ0haVhSQCJ0^JaJ0!jhaVhSQCJ0U^JaJ0j("hUj/H hUVjhUjH h* UVh* jh* Uh h^J h* ^J hSQH*^J hSQ^JL   : ; < _ ` a h^h & F hdh^hgddh     6 7 8 9 < = [ \ ] ^ ` a b ŻﮤvijToG hSQUV^Jj hSQU^Jj[ToG hSQUV^JjuhSQU^Jj/ToG hSQUV^JjmhSQU^JjSoG hSQUV^JjbhSQU^JjSoG hSQUV^JjXhSQU^JjjSoG hSQUV^J h^J hSQ^JjhSQU^J%   ! 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% & %  6 N % & % (   A % ( ' % & %  6 N  A % ( ' % ( %  %  % ( %  %   TT5 D@Ć@ LPO? % & %  6 B % & % (    % ( ' % & %  6 B   % ( ' % (  % ( % & %  6  % & % (    % ( ' %  % ( % & % % 6  % & % (    % ( ' % & % % 6    % ( ' % ( & % % 6    % ( ' % ( % w %  % ( % w % w  TT,@Ć@w LPT,   TT,@Ć@ LPf % % %  %  %   TTET@Ć@ LPt   TTET@Ć@ LPr   TTET@Ć@ LPi   TTET@Ć@ LPf   TTET@Ć@ LPl   TTET@Ć@ LPu, F  TTET@Ć@F LPo, t  TTET@Ć@t LPr   TTET@Ć@ LPo,   TTET@Ć@ LPmE   TTET@Ć@ LPe, 2  TTET@Ć@2 LPt I  TTET@Ć@I LPh, x  TTET@Ć@x LPy,   TTET@Ć@ LPl   TTET@Ć@ LPs,   TTET@Ć@ LPu,   TTET@Ć@ LPl  TTET@Ć@LPp, L TT!E'T@Ć@LLPh, z TT(E.T@Ć@zLPo,  TT/E5T@Ć@LPn,  TT7E=T@Ć@LPy,  TT=E?T@Ć@LPl % %  F%  F TTRa@Ć@ FLPo,  F TTRa@Ć@ FLPr % %  F%  F TTRa@Ć@ FLP   F TTRa@Ć@ FLPt & F TTRa@Ć@& FLPr F F TTRa@Ć@F FLPi ^ F TTRa@Ć@^ FLPf z F TTRa@Ć@z FLPy,  F TTRa@Ć@ FLPl  F TTRa@Ć@ FLP   F TTRa@Ć@ FLPg2  F TTRa@Ć@ FLPr ) F TTRa@Ć@) FLPo2 \ F TTRa@Ć@\ FLPu2  F TTR a@Ć@ FLPp2 % F CDIFVjCD0100ChemDraw 8.0e&\` 3 g&4s @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$d'`:$$efa9+ULIefa9+ULS yy T9yKNi +}Ke2SuKej}l# `SUlN 7Vl 7W yە X 7YN 7lLeli +723īeefāěiQm# `On li +72̄ee&̄eLQm# `Op̌y,U 7ry +7ff}u#`CH3 ST  SU  UV  VW Z WX s[[ XY \ SY [m Tlo Tnq Tp s Wr e&_9k S8e&_9k S8v[) +7fz%r%Q}S8#`CH3vK +zK22sK2*{# `S c̬ +72fe&_Lg# `O̬̊ +72e # `OLwl 7      e&\9 e&\9 s۴ 7;Ta( s۴ c!fe۴ d +liTaliI# `F"sJ5 e +fwJoJfw# `F#9۴ f +H~I# `F(s g ) h( $ i !% j "& k #fwCoCQz#`CF3sK +wK2pK*xX# `S `, +72cDe&\DLd# `Ȯ, +72DeD # `OLt 7      ?w43@}C@z4 7@zC 7  t3{x 7x 7  tT5~x 7<+$T*+p lY4C m+?42s4# `SF(  CDIFp n+m#$T# `OY o+?2sgδ `O p* q r|tT5~/An atom in this label has an invalid valence.#Msq u3x u u 7u  7   2q_v{fi uHc 7=c>=-K,"Q s-M t +{ { Z3# `F.Or u +6>^>6}X# `F/t v +ڛcڛ# `F0P w+v a W `S1Pf x+v ~~P K `O2(Q y+%,QX%Q=- `O3 z,04 {015 |026 },-7 ~,.8 ,/y(`2q_v{fi/An atom in this label has an invalid valence.#Tf~ v` Uu+ /An atom in this label has an invalid valence.Ts2f`2 l &ChemDraw can't interpret this label.!Ap-toluenesulphonyl or tosyl group ̬+ &ChemDraw can't interpret this label.5methanesulphonyl or mesyl group f3e3 &ChemDraw can't interpret this label.(>trifluoromethylsulphonyl or trifyl groupF, DMHCGRTS.  x ( `2 / $& $R k `@ `l ! M "!     R I; K  Ql v v x:} } $ v  o $ o < < ~ ~      TfMsCF3 S O O CH3SOOSOOCH3   }~ 5      ``  [!! #6 ``  ]  c!& ``  2 !5 ``  M !5 ``   f ``   @ ``  nO ``  %  ,O ``   * { `` 7> ``  R  Y ``  /     J jTs!      t !p-toluenesulphonyl or tosyl group    u imethanesulphonyl or mesyl group(    9 $-(trifluoromethylsulphonyl or trifyl groupArialFh [ MDLSKXY Ariald 0 CXEAArialdTs 0 @X!ArialdArialdArialdp-toluenesulphonyl or tosyl group 0  XArialdArialdmethanesulphonyl or mesyl group 0 mX(ArialdArialdtrifluoromethylsulphonyl or trifyl group 0 !% bDhD!S% ޡDD!% ]bD@؇D!% BD@؇D!% RDhD!% BDD!% ]bDD!O% ǃD?}D!O% ǃDOD!% TDD!%b DD ' ' '(. ' '(. ' '(. '( '( '  '  0  !%b O9ED!S% /ED!O% 0EwD!O% 0ED!% d#ED ' '( '( ' 0  !CF3 !% EؐD! F% E}D! F% EؐD! F% EǢD! EؐD ' ' ' '"4CF36=  EؐD<!S% wED!O% EpD!O% ED!% zE_D ' '( '( ' 0!% 0DИD!% )DИD '( 0!% ED!% dED '( 0!Ms!% \sB!S% !AC!O% #C!O% EAC ' '( '("4Ms6= ED< 0!% 4iE@D!% rE@D '( 0!Tf!% k\!C! F% ä9B! F% iC! F% l~ ZB!S% |GÐюC!O% @_юC!O% kûC ' '( '( ' ' '"4Tf6= ^ED<% % CONTENTSs_1222753071 !mA. 0 0Ole EPRINT $VjCD0100ChemDraw 8.0e&\` 3 g&4s @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$dd'`:$$efa9+ULIefa9+ULS yy jT9yKNi k+}Ke2SuKej}l# `SUlN l7Vl m7W yە nX o7YN p7lLeli q+723īeefāěiQm# `On li s+72̄ee&̄eLQm# `Op̌y,U u7ry w+7ff}u#`CH3 cST  dSU  eUV  fVW Z gWX s[[ hXY \ iSY [m rTlo tTnq vTp s xWr e&_9k S8e&_9k S8v[) ~+7fz%r%Q}S8#`CH3vK +zK22sK2*{# `S c̬ +72fe&_Lg# `O̬̊ +72e # `OLwl 7 }     e&\9 e&\9 s۴ 7;Ta( s۴ (!fe۴ ) +liTaliI# `F"sJ5 * +fwJoJfw `F#9۴ + +H~I `F(s , ) -( $ . !% / "& 0 #fwCoCQz#`CF3sK +wK2pK*xX# `S `, +72cDe&\DLd# `Ȯ, +72DeD # `OLt 7      ?w43@}C@z4 y7@zC z7 { t3{x 7x 7  tT5~x 7<+$T*+p DY4C E+?42s4# `Sp F+m#$T# `OY G+?2sgδ `O H* I J|tT5~/An atom in this label has an invalid valence.#Msq u3x u u 7u  7   2q_v{fi uHc 7=c>=-K,"Q R-M S +{ { Z3 `F.Or T +6>^>6}X `F/t U +ڛcڛ `F0P V+v a W `S1Pf W+v ~~P K `O2(Q X+%,QX%Q=- `O3 Y,04 Z015 [026 \,-7 ],.8 ^,/y(`2q_v{fi/An atom in this label has an invalid valence.#Tf~ v` Uu+ |/An atom in this label has an invalid valence.Ts2f`2 l &ChemDraw can't interpret this label.!Ap-toluenesulphonyl or tosyl group ̬+ &ChemDraw can't interpret this label.5methanesulphonyl or mesyl group f3e3 &ChemDraw can't interpret this label.(>trifluoromethylsulphonyl or trifyl groupAl[es> EMF$    ^i  KRp8"Arialx9h98H1 @H1x9 9L||||x9|84@a01 XH1h9XH1X`H1x9X9|||||9|dv%   &% b 6  % &% (  z  % ( '%  % ( % &% b 6x  % &% (  z  % ( '%  % ( % &% x 6x  % &% (  z  % ( '% &%  6   z  % ( '% (  % ( % &% x 6R  % &% (  z  % ( '%  % ( % &% R 6H  % &% (  z  % ( '% &% 9 6 2  z  % ( '% (  % ( % &% H 6H  % &% (  z  % ( '%  % ( % &% b 6H  % &% (  z  % ( '% &% { 62  z  % ( '% ( %  %  % ( %  Rp"Arial P@4P999|X9 ||||9|dv%   TT)4@|@ LPS8 % % [ % [ % [  TT4@|@[ LPO? % &%  6i  % &% (  [  % ( '% &%  6i  [  % ( '% ( %  %  % ( %  %   TT5D4@|@ LPO? % &%  6\  % &% (    % ( '% &%  6\    % ( '% ( %  %  % ( %  %   TT*4@|@ LPO? % &%  6`  % &% (    % ( '% %  %  % ( %  %   TT*4@|@ LPC8   TT*4@|@ LPH8 % Rpj"Arial|8ex9Heă`UUUU%o@b@b@|b@x9`UUUU%o@ăJW@1 d1h91X11x9X9$$jt||||9|dv% ' Rp"Arialwtw w wt!^K %ېxPD40'3PPl9H1 Pb@(4H P 4P9 91X9b@||||9|dv% '  TT!-4@|@' LP3& % % &% R 6  % &% (  '  % ( '% %  %  % ( %  %   TT@H*4@|@ LPC8   TTJR*4@|@ LPH8 % %  %   TTS!X-4@|@ LP3& % % + % +  TTYa*4@|@+ LPC8 g  TTck*4@|@g LPH8 % %  %   TTl!q-4@|@ LP2& % % &%   6  % &% (    % ( '% %  %  % ( %  %   TT +4@|@ LPN8 R  TT +4@|@R LPu,   TT+4@|@ LP: % %  %  %   TT")*4@|@ LP+2 % % % V07#?(  % %  6 % % V,%8&   % %  % %    % '%  % ( % &%  6t  % &% (    % ( '%  % ( % &%  6x  % &% (    % ( '%  % ( % &% x 6x  % &% (    % ( '% &%  6|    % ( '% (  % ( % &% x 6  % &% (    % ( '%  % ( % &%  6H  % &% (    % ( '% &%  6{2    % ( '% (  % ( % &% H 6H  % &% (    % ( '%  % ( % &%  6H  % &% (    % ( '% &%  62    % ( '% ( % 5 %  % ( % 5 % 5  TT)4@|@5 LPS8 % % 1[ % 1[ % 1[  TT4@|@1[ LPO? % &% B 6Ci  % &% (  1[  % ( '% &% ` 6ai  1[  % ( '% ( % 1 %  % ( % 1 % 1  TT5D4@|@1 LPO? % &% ` 6a\  % &% (  1  % ( '% &% B 6C\  1  % ( '% ( %   %  % ( %   %    TT*4@|@  LPO? % &% , 6  % &% (     % ( '% % ! %  % ( % ! % !  TTCK*4@|@! LPC8 ]  TTLT*4@|@] LPH8 % %  %   TTV![-4@|@ LP3& % % &%  6  % &% (    % ( '% % M  %  % ( % M  % M   TTT\-4@|@M  LPC8    TT^f-4@|@  LPH8 % %  ) %  )  TTg$l04@|@ ) LP3& % %   %    TTmu-4@|@  LPC8 $   TTv~-4@|@$  LPH8 % % ` ) % ` )  TT$04@|@` ) LP2& % % %   %   %    TT-4@|@  LPN8    TT-4@|@  LPu, % &%  6  % &% (     % ( '%  % ( % &% % *@ z v % L 6l % ( %   %   %    TT,4@|@  LP+2 % % ) % ) % )  TTDS4@|@) LPA8 a  TTDS4@|@a LP  x  TTDS4@|@x LPt   TTDS4@|@ LPo,   TTD$S4@|@ LPs,   TT%D+S4@|@ LPy,   TT,D.S4@|@ LPl #  TT/D5S4@|@# LPa, Q  TT6D9S4@|@Q LPt i  TT:D@S4@|@i LPe,   TTADDS4@|@ LP    TTEDGS4@|@ LPi   TTHDNS4@|@ LPs,   TTODRS4@|@ LP    TTRDXS4@|@ LPa, 0  TTZD`S4@|@0 LPn, ^  TTaDdS4@|@^ LP  u  TTeDkS4@|@u LPa,   TTlDnS4@|@ LPl   TToDuS4@|@ LPc,   TTvD|S4@|@ LPo,   TT}DS4@|@ LPh, <  TTDS4@|@< LPo, j  TTDS4@|@j LPl }  TTDS4@|@} LP    TTDS4@|@ LPd,   TTDS4@|@ LPe,   TTDS4@|@ LPr    TTDS4@|@  LPi   TTDS4@|@ LPv I  TTDS4@|@I LPa, w  TTDS4@|@w LPt   TTDS4@|@ LPi   TTDS4@|@ LPv   TTDS4@|@ LPe,   TTDS4@|@ LP. % % Rp8"Arial|2|||L͢88|2|||((8H9P9X92| h99 B0|t|| P 4P9|y6||X\9||||9|dv% % Rp8"Arial|2|||>88|2|||PP@=H9P9X92| 99dD0|t|| P 4P9|إD||X\9||||9|dv%  %  %   TTDS4@|@ LPT,   TTDS4@|@ LPh,   TTDS4@|@ LPe, 0  TTDS4@|@0 LP  H  TTDS4@|@H LPL, v  TT D S4@|@v LP.   TT DS4@|@ LPG?   TTDS4@|@ LP.   TTDS4@|@ LP    TTD S4@|@ LPi    TT!D'S4@|@  LPs, 9   TT(D+S4@|@9  LP  P   TT,D2S4@|@P  LPc, z   TT2D8S4@|@z  LPa,    TT:D<S4@|@  LPl    TT=D?S4@|@  LPl    TT@DFS4@|@  LPe,    TTGDMS4@|@  LPd, )   TTNDQS4@|@)  LP  A   TTRDXS4@|@A  LPa, % % o  Rp"Arialwks(kk+PӣwTk  92|x99(5X9| PH4P9G=|X(92|||||9|dv% o   TTYD\S4@|@o  LP     TT]DcS4@|@  LPp, % %   %    TTeDhS4@|@  LP-    TTiDlS4@|@  LPt    TTmDsS4@|@  LPo,    TTtDvS4@|@  LPl (   TTwD}S4@|@(  LPu, W   TTDS4@|@W  LPe,    TTDS4@|@  LPn,    TTDS4@|@  LPe,    TTDS4@|@  LPs,    TTDS4@|@  LPu, 9   TTDS4@|@9  LPl L   TTDS4@|@L  LPp, z   TTDS4@|@z  LPh,    TTDS4@|@  LPo,    TTDS4@|@  LPn,    TTDS4@|@  LPa, 3   TTDS4@|@3  LPt J   TTDS4@|@J  LPe, y   TTDS4@|@y  LP     TTDS4@|@  LPi    TTDS4@|@  LPo,    TTDS4@|@  LPn,    TTDS4@|@  LP    TTDS4@|@ LPo, D  TTDS4@|@D LPr % % ` Rp"Arialm|wks(kk+XӣwTn 7wZw 0wH PH4P9=;X9ې||||9|dv% `  TTDS4@|@` LP  x  TTDS4@|@x LPt   TTD S4@|@ LPo2   TT DS4@|@ LPs&   TTDS4@|@ LPy, "  TTDS4@|@" LPl 9  TTD$S4@|@9 LPa2 h  TT%D(S4@|@h LPt   TT)D0S4@|@ LPe2   TT1D4S4@|@ LP    TT4D7S4@|@ LPi   TT8D?S4@|@ LPo2   TT@DGS4@|@ LPn2 % % z % z % z  TTV e4@|@z LPME Vz  TTVe4@|@Vz LPe, z  TTVe4@|@z LPs, z  TTV"e4@|@z LPy, z  TT#V%e4@|@z LPl z  TT&V,e4@|@z LPa, z  TT-V0e4@|@z LPt /z  TT1V7e4@|@/z LPe, ]z  TT8V;e4@|@]z LP  uz  TT<V>e4@|@uz LPi z  TT?VEe4@|@z LPo, z  TTFVLe4@|@z LPn, z  TTNVTe4@|@z LPs,  z  TTTVWe4@|@ z LP  %z  TTXV^e4@|@%z LPa, Sz  TT_Vee4@|@Sz LPn, z  TTgVme4@|@z LPd, z  TTnVqe4@|@z LP  z  TTrVue4@|@z LPt z  TTvVye4@|@z LPr z  TTzV|e4@|@z LPi  z  TT}Ve4@|@ z LPf $z  TTVe4@|@$z LPl 6z  TTVe4@|@6z LPa, dz  TTVe4@|@dz LPt |z  TTVe4@|@|z LPe, z  TTVe4@|@z LP  z  TTVe4@|@z LPi z  TTVe4@|@z LPo, z  TTVe4@|@z LPn, 0z  TTVe4@|@0z LPs, Zz  TTVe4@|@Zz LP  qz  TTVe4@|@qz LPa, z  TTVe4@|@z LPr z  TTVe4@|@z LPe, z  TTVe4@|@z LP  z  TTVe4@|@z LPs, *z  TTVe4@|@*z LPi =z  TTVe4@|@=z LPmE z  TTVe4@|@z LPi z  TTVe4@|@z LPl z  TTVe4@|@z LPa, z  TTVe4@|@z LPr z  TTVe4@|@z LP. % F CDIFVjCD0100ChemDraw 8.0e`? c g&4s @@' :;<   `  fx# $$$$2ArialxXX$dg(XX$d'`n$$exm̌Gexm̌G`/ \y/KN ]+_3K2+K3# `S"N ^7" _7`/ `; a7;N b7̌l c+72s̄ēQ# `OLCl e+723Ḡef?̄̌GQ# `O /, g+723De+D 4# `O!/ i+7f3+16#`CH3./ k7ol)4`950 Kal)G Ld850و M e Ndab O`af3+xm16#`CH3CH2" U # V $ W #%% X & Y ,%'' Z ( [ #"') d* f+ h  , j! / l . 4ex<̌G5ěG6`/ w7y/Kη x+_3Kr2+Kr3# `S8" y79" z7:`/[ {;; |7<; }7=̌ ~+72seѻ# `O>LC +723Gef?̌Gѻ# `O?/̬ +!723ğe+ğ 4# `O@/  +7f3+16#`CH3H p67 I q68 J r89 IKK s9: L t:; RKMM u;< N v6< IHMO 7=P 7>Q 7? 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