ࡱ> !v%` bjbj"x"x 4*@@HHH\....,.<\>>.////444<>>>>>>>>>>>>>$?>43444>//>5554//<>54<>55V0=@&"H=/. `,XhH.4Xp= <>>0>|=xB55XB=BH=Hy4y45y4y4y4y4y4b>b>5y4y4y4>y4y4y4y4\\\$\\\\\\ Practice for EXAM 3 Provide the product of each reaction shown below. Include stereochemistry.  EMBED ChemDraw.Document.6.0  Provide a full mechanism which includes intermediates and use curved arrows to show electron flow.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Draw a mechanism to show why the reaction of vinylcyclohexane with strong aqueous acid gives two constitutional isomeric products, (1-hydroxyethyl)cyclohexane and 1-ethyl-1-cyclohexanol. Draw a free energy diagram for the acid-catalyzed ring opening of the following epoxide. Include structures for transition states and intermediates.  EMBED ChemDraw.Document.6.0   SHAPE \* MERGEFORMAT  Draw nice chairs to show the anti conformation for dehydrohalogenation (E2) of the following substrates. Indicate which substrate gives primarily the Hofmann product and which gives the Zaitzef product. a. cis-1-chloro-2-methylcyclohexane + NaOCH3 in CH3OH b. trans-1-chloro-2-methylcyclohexane + NaOCH3 in CH3OH Draw the mechanism to show formation of all possible intermediates and all possible alkenes.  EMBED ChemDraw.Document.6.0  Draw a complete mechanism to show how this ring expansion occurs.  EMBED ChemDraw.Document.6.0   Complete these short syntheses. Draw the missing structures. a.  EMBED ChemDraw.Document.6.0  b.  EMBED ChemDraw.Document.6.0  c.  EMBED ChemDraw.Document.6.0  Starting with the terminal acetylene compound I show how to prepare alkene II in with cis stereochemistry.  EMBED ChemDraw.Document.6.0  Energy Reaction Progress ajk    % & ' ( 1 2 P Q R S ^ _ } ǼǰumbZj7)hs^UjTL hs^UVjhs^Uj#L hs^UV hs^hs^CJOJQJ^JaJhs^hs^OJQJ^Jhs^CJOJQJ^JaJhs^h@ jhs^UjRL hOUVhOjhOUhlxCJOJQJ^JaJhs^hlxB*^Jph hhhB*^Jphabcdefghijgdlx&&#$/7$8$H$gds^gdlx $ & Fa$gdgd $v^va$gd   ) * + , - . / 0 1 T U V W & F7$8$H$gds^ 7$8$H$gds^gdlxW X Y Z [ \ ] ^ I J K L M N & F7$8$H$gd4ygdlx} ~  H I J V      / 0 1 2 3 4  0 ཯uum`P`h Ph P6OJQJ]^Jh Ph POJQJ^JjGh4yUjh4yUmHnHuj<<h4yUjL h4yUVjh4yU h4yh4yCJOJQJ^JaJh4yCJOJQJ^JaJh4y hs^hs^CJOJQJ^JaJhs^CJOJQJ^JaJhs^jhs^Uj3hs^UjlL hs^UVN O P Q R S T U V    4  ; < = > ? @ A B C gd P & Fgd P & F7$8$H$gd4ygdlx0 1 7 8 H M t u { |     S T r s t u | }  䟎ziXNh POJQJ^J!j_h Ph POJQJU^J!j`Sh Ph POJQJU^J'jJ/E h Ph POJQJUV^J!jHh Ph POJQJU^J'j/E h Ph POJQJUV^J!jh Ph POJQJU^Jh Ph P5OJQJ\^Jh Ph P6OJQJ]^Jh Ph POJQJ^Jh Ph PH*OJQJ^JC        R S v w x y & Fdhgdh% & Fdhgd Pgdlxgd Py z { | ~  gd)J & Fgdh%gd P %&DEFGIJxz཭ࣝࣝyokdkdk]kUkjhh%U hh%6] hh%5\hh%jh)JCJUjiG h)JCJUVjh)JCJUjjG h)JCJUV h)JCJjh)JCJUjh)JCJOJQJU^J%jgG h)JCJOJQJUV^Jjh)JCJOJQJU^Jh)JCJOJQJ^JhOJQJ^Jh)JOJQJ^J! !HIJ 7$8$H$gdh% & F7$8$H$gdh%gd Pgd)JhDh4y hh%hh%jhh%UjMhh%Uj!L hh%UV21h:p1Z/ =!"#$% Dd 0  # A"|[u8nc)ˌDd @=|[u8nc)ˌ/GO+x |E{gz$v!9hn' ,!"DuU h@#a:#Mbǡr4 ȇF|xfg%5tbQw,X%vڗ.< 3;F}VA:1h!΃_'7x^~2fL9n63lو| 県W d/DCISת]e4@xu e =YHsiu;m5OG|AjLu6gh4 A||l`׸t0!i^ [h??A}#nO> DZ~-<հ,wݻ܆bQWtaнu.!t%!t]U.dNu !}i g8dL6A=k\gCEvsa3Hm쿬u׈V{eX??wc8(Ov7G]f򮲏XHoAx3loNˢC7"kw_wY+.D$ψfs-4\Vmowq\Bg]ЭRD}[؟qFu(ld<~[[dί$t=S328[~X>&{e7}]Cmv-?K8ǚ N[&|i0\x;w+/rǽG>g-x}V`mԾ8}k6ﶙ7}8n OBeeL扮vso="+b/`o6q-} {aϳ[4+6?*`Jaiq\J`)dN^C !A\z-֋J*YT\, 3veq[,O أ({}";m⼒.T K;%t>3"3hSrż_4Ө}8erM]a_o*>q9]MpiE6ۊ#{~:bޣXY5FGss-=g9>wqߓ܏MK;>({F}\kܯPK;wǾL.E5 hطr}g}n}˩}+8ۢ}S~.o{^aIۚǎR )zEbPC({1=D:}Wp7gWcn-Mꂟ܂K0Hu/<.`wqlQ`3gPv_EbWq3{PY"`_Hٙ-"?Eٹ"?UΣVRA_B.qٳi)})"L] `_F٥vr){&]c*kK)Rqs؏[doEv!}k9&ʾTܼ]-`/ټH.({gi<}W5 L.?QQ? TkIΚ긽uIuK3[ag"!6?x/k6"7w 34L.9)ҳ?sS%,)wM-q}o@\Sp<ҹ.X*s n>;α^hltԴ597Z86ڭ_.)Ʌ}\#n~հ({;/puk5=?巳{9;G9A9] ث({-zGjMMXOuÕ8{TlS__ Q_ ۭ"__ Q_ __ Q_ v{ e䰷[d0 2:p> `r,55þ"{` YL9gg&qCA|Gҿnԗɵ>¯<}_}c_&גC=m/`A9揧Hybi<}ߣӯ\k{IЯ^_Ծ8}{vǭٞ/9?@/{NT^rZmrTH{yP3| rh|wu6Wi5KXT;{̶~ݑJuĹ]<8q?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmpqrstuxyz{|}~Root Entry7 FR~hH"@hData WordDocument64*ObjectPool9)`,XhHR~hH_1288410706!mA. `,XhH`,XhHOle EPRINT#ObjInfo  !"#$%&'()*+,-./0123456789=>?@ABCDEFGHIJKLMNRSTUVWXYZ[\]^_`abcdefgklmnopqrstuvwxyz{|} VjCD0100ChemDraw 8.0.33V @:96`  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXXrjVg(XXrl(8e# EMF:,p   d . 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TTFDPV~@@LPHE % % %  TTQKVY~@@LP2& % % '% ' TTWDbV~@@'LPOK % % o% o TTcKhY~@@oLP2& % % %  TTiDlV~@@LP,  TTmDpV~@@LP   TTqD|V~@@LPNK  TT|DV~@@LPa, ; TTDV~@@;LPOK  TTDV~@@LPHE % % x% x% x TT$~@@xLPwE x TT%+~@@xLPa, x TT,0~@@xLPr <x TT2<~@@<xLPmE x TT>A~@@xLP, x TTBE~@@xLP  x TTFL~@@xLPc, x TTMT~@@xLPo2 x TTU[~@@xLPn@, Kx TT]c~@@KxLPc, xx TTdg~@@xxLP. x TThk~@@xLP  x TTlw~@@xLPKK x TTx~@@xLPMX Kx TT~@@KxLPn, }x TT~@@}xLPOK % % %  TT~@@LP4& % % x% x TT~@@xLP  % % %  TT$~@@LPHE % % %  TT%*~@@LP3& % % %  TT+6~@@LPOK % % \% \ TT7=~@@\LP+, % % % % V0Q1^; W 5S ?  % % Q 6+% % V,7UdV "1*Q % %  % %  \ % '%  % ( % % % V0mu l   s l% %  6 &% % V,>p  * " % %  % %  \ % '%  % ( % % % V0 h *r h  % % p 6d % % V,Wr c c r % %  % %  \ % '% % $ %  % ( % $ % $  TT~@@$ LPHE % % l7% l7 TT ~@@l7LP2& % % % $% $ TT#~@@$LPP8 \ TT #~@@\LPd2  TT #~@@LP/   TT#~@@LPCE % % c % c % c  TT.(8:~@@c LPCE   TT8(::~@@ LPl % %  0%  0 TT=/B=~@@ 0LP2& % % %  3%  3%  3 TTgUtg~@@ 3LPMX  3 TTuUg~@@ 3LPCE c 3 TTUg~@@c 3LPP8  3 TTUg~@@ 3LPB?  3 TTUg~@@ 3LPAE % % % ] l% ] l% ] l TT~@@] lLP12  l TT~@@ lLP.  l TT~@@ lLP  % %  l%  l TT~@@ lLPOK  l TT~@@ lLPs& 0 l TT~@@0 lLPOK % % x % x  TT~@@x LP4& % % % ] % ]  TT~@@] LP22   TT~@@ LP.   TT~@@ LP    TT~@@ LPNK   TT~@@ LPa, 6  TT~@@6 LPHE ~  TT~@@~ LPS8   TT~@@ LPOK % %  %   TT~@@ LP3& % % # % #  TT~@@# LP, <  TT~@@< LP  U  TT~@@U LPHE % %  %   TT~@@ LP2& % %  %   TT~@@ LPOK % % % V0S_  AEY  % % F6t% % V,\Bsx G% %  % %    % '%  % ( % % % V0 a v x  % % t 6zL% % V,t xIMx % %  % %    % '%  % ( % % % V0(\ J ^ t \ % % ^ 6iz% % V,Z fynyb % %  % %    % '%  % ( % % % V0=H P K 7  % %  I 6% % V,B  N  I % %  % %    % '%  % ( % % % V0    n % %  6, % % V,M ) -  % %  % %    % '% % % %  % ( % %  TT ~@@LP12 H TT ~@@HLP. a TT~@@aLP  % % z% z TT~@@zLPHE  TT$~@@LPg,  TT&*~@@LP(  TT,7~@@LPOK ^ TT7A~@@^LPAE  TTCI~@@LPc,  TTJN~@@LP) % % %  TTOT~@@LP2& % % %  TTUX~@@LP, 2 TTY\~@@2LP  K TT]e~@@KLPE8  TTgj~@@LPt  TTlw~@@LPOK  TTw~@@LPHE % % i% i TT ~@@iLP22 Hi TT ~@@HiLP. ai TT~@@aiLP  zi TT~@@ziLPNK i TT$~@@iLPa, i TT%.~@@iLPB? 2i TT0:~@@2iLPHE % % z% z TT<A~@@zLP4& % % % m % m % m  TT~@@m LPHE   TT~@@ LPI % %  %  %   TT~@@ LPB?   TT~@@ LPr % %  %   TT ~@@ LP2& % % $ % $  TT~@@$ LP, =  TT~@@= LP  V  TT ~@@V LPHE % %  %   TT ~@@ LP2& % %  %   TT~@@ LPOK % % %  %  %   TTCJ~@@ LP12   TTKN~@@ LP. 1  TTOR~@@1 LP  % % J % J  TTS^~@@J LPOK % %  %   TT^c~@@ LP3& % % %  2 %  2  TTCJ ~@@ 2 LP22  2  TTKN ~@@ 2 LP. 1 2  TTOR ~@@1 2 LP  J 2  TTSW ~@@J 2 LP( l 2  TTXb ~@@l 2 LPCE  2  TTcm ~@@ 2 LPHE % %  I %  I  TTns ~@@ I LP3& % %  2 %  2  TTtx ~@@ 2 LP) % % = I % = I  TTy~ ~@@= I LP2& % % c 2 % c 2  TT ~@@c 2 LPS8 % %  %  %   TTpz~@@ LPCE B  TTz~@@B LPHE   TT~@@ LPB?   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NaBH4A@%3`L( Q&ChemDraw can't interpret this label.`Br2, H2OB 03 0Hld R&ChemDraw can't interpret this label.&`1. O3 2. (CH3)2SCQ3Q  S&ChemDraw can't interpret this label.`CHBr3, KOH v <   mp<A =    iSk >   !^ ?   (y`D` C   )oW'- D   *  ? 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