ࡱ> hx%` bjbj"x"x .$@@"<<<8t,$B$($h`B YaW'<0B09XB << 1. For each molecule, place an asterisk (*) next to each asymmetric center. There may be more than one stereogenic center in some molecules. (Notice that the terms stereogenic and asymmetric center are synonyms.)  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  2. Apply the symmetry plane test and indicate which of the following molecules are chiral. (Circle your choices.)  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  3. Assign absolute configuration to each molecule.  EMBED ChemDraw.Document.5.0  4. Shown below are Newman projections of the four stereoisomers for 2-chloro-3-methylpentane: (R,R)-, (S,S)-, (R,S)-, and (S,R)-2- chloro-3-methylpentane.  EMBED ChemDraw.Document.6.0  a. Assign R,S configuration to each Newman structure.  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  b. Which isomers, if any, are meso? 5. Is it possible for a molecule to have one or more stereogenic centers and yet be achiral? 6. Is it possible for a molecule to be optically active if it is achiral? 7. What is the maximum number of possible stereoisomers for each of the following compounds? (It may be helpful to place an asterisk next to each asymmetric center.)  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[W' [W'Ole CompObj*,~     ,1 !"#$%&'()*+-./0DH3456789:;<=>?@ABEFG[ZJKLMNOPQRSTUVWXYq\]^_rabcdefghijklmnopwstuvz{|}~VjCD0100ChemDraw 8.0G>GrX/   @@' :;<   `  cf%N "p_x# $$$$2Arialx,, 8 ` g(,, 8 `dd'`$$w7M>Gr{a[G `7GZS aa` c01! GZ Em e7-n` g+7]Gq7]]k7]rl#`NH2%a{ i7#PT k+7RDQw7MDQ3RV# `O b 8s|( x  d 8s|( x   f 8s|( x ! h 8s|( x " j $ l#&wJfo'5_[ m(W n7)5_ڡ p*WD r+k t+7^n#^h#o#6#`Cl2M v+7yPwJ3PD# `O4@j@ x+7lwwg3m# `O6@^@ z+7`ww[3a#`OH8Y |+7y\<wVf3\<#`HO- o 8s|( x(' . q 8s|( x)( / s 8s|( x*) 0 u 8s|( x)+ 3 w*25 y'47 {*6 9 }'8 =wKn coE>_ ~?X>% @_1 B؏l 1 +7qIo /Oi / co 4# `ODk  +7m 7h Fm D# `OFZ +79]|WnES]|#`HOQN@% +79Q"wK"3SQ-#`OHSW@= +79Z:wT:3SZE#`OHG  8s|( x?> H  8s|( x@? J  8s|( x@BL >DN >F R ?Q T @S W3H|^ɭkXdW[p Y^| ZdW [J +7UMԆ3HԆMT# `O\ZL@p +7OmIm-Os# `O]\f +7_ ?.bD ]D-d#`OCH3`  8s|( xYX a  8s|( xZY b  8s|( xZ[c X\d X] e Y^ f Z_ hGhnX/it"U!@ jt"a! k Y\A 7l<_ m <`BrZ~u~#: 8,9; 9su= ;`Bryqz#< :,;u s v t7uw u& x v7w@ > A ? B @}C A@AD BABE C@BF D~&P N `H Zy&͂&G E@FH FQ O`CH33+I G@HJ HO M`CH3M~0+K IAJL JN L`CH331+M KALR PS QsT RU SV TW UX VRSY WSTZ XTU[ YUV\ ZVW] [RW^ \ڗ f d`BrZ #_ ]T^` ^Z}d b`CH3ځy+a _V`b `sͽe c`CH3+c aVbg ezPq o`C(CH3)3&MvNy+++ h fZP01mioki gghj hsCr p `IfBCD5k ihjl j͞\m khln lsdp n `Haaho mhns q͞ot rlsObjInfo/1CONTENTS _11585824204!mA. [W' [W'Ole $ArialTimes New Romanx,, 8 ` g(,, 8 `dd'`W$$(̌rN''ګr 97)Q :+ګŵ <-9׼ >7/ګ @71; B+7g_k_K'_K#`qCl3fƣ D+72]̌]n23]>#`qCH3* ;)' , =+) . ?-+ 0 A/- 2 C)1 4 E+3 5̌'K6ګ; F7Xګ+E<ګ; .>; / ? 0><:\#`qMe7 G8ګ#8 I9Un K7Yu %6*A%6* 1B%; 2D%; 3 E 4DBF 5AB!4wK#`qEt;; M+7g k'#`qCl<fƣ3 O7ZfƣBHfƣ3 6If3 7 J 8IH2V̌VH# #`qMe= H76 > J87 ? L98 A N7; B P8< QTS@P@ R7R S7S TPR HX5PX5ղ؛ Q5This label has conflicting or unassignable charges.$2-chloro-3-methylpentane VjCD0100ChemDraw 8.0P[}>Qpy  @@' :;<  EPRINT35d ObjInfo6CONTENTS_11585824312A9!mA. [W' [W'lPU EMFd     TV KRp8"Arial|8v?oJJxxDxxJJxxqJxhx HTJx8wJw|Jxf4Pt XonJoJwxw:w||dv%   % % Rp"Arial"j ~D Hw2w`wj ~sDw/X(DDw/P\4P  XobH&?lwxw:w||dv%  TT*F4U@"5@LPMsE C TT5F;U@"5@CLPei, % &%  6  % &% (  C % ( '% % %  % ( % %  TTHP#@"5@LPHW8 % &% A6 % &% (   % ( '% % (%  % ( % (% ( TT#@"5@(LPE\8 _ TT#@"5@_LPtm % &% 6 % &% (  _ % ( '%  % ( % % % *wK% % &% % *wK% % ( % :% :% : TT*2@"5@:LPCP8 8: TT35@"5@8:LPlo % &% 6L % &% (  8: % ( '% % u%  % ( % u% u TTG2OA@"5@uLPH\8 % &% 6< % &% (  u % ( '% %  u%  % ( %  u%  u TT2 A@"5@ uLPMWE Nu TT2A@"5@NuLPe0, % &% D6 % &% (  Nu % ( '% FCDIFVjCD0100ChemDraw 8.0P[}>Qpy  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$d'`M$$P[}>Qpy4i4BQpy Q` ,7NQ@[d=Q` !?Q` " @ #?=[?ŏ[Qfi#`Me!Jz` -2This atom is very close to another atom or bond."FmZu /+7qZ=r4iZ=rqpy# `H#Fm@J 17O.KUE[|izB|iz $CmV` %EOU` & F 'ECG (BCqK4i4ByqK#`Et$ .! % 0!"  & 2#!  P[}>xxl6_@_ 4+7c[P[[}gcfe#`Cltlx@_ 52This atom is very close to another atom or bond.xZu 7+7Z}qfZ}qx# `HxI 97PxDDԧLNIxI )JxI * K +JIdLf}>xdL#`Me 6 &% 8 %$ : &$lflvy` 3  FdVDMHCGRTS*!  x (XP`5. " }3pq4 hq5 d %7 d9 , - 4/168:.02ClH MeMeH Et `` )") ``    m ``     ``  - ;- C `` G | `` G,ArialTimes New RomanF@2MDLSKXY Ariald 0 !Me!% pD壸D! pD#D ' "4Me6=  pD壸D<!% pD\ D!H% JD^D!Et!% D&*D!% W pD(jD! T pDOGD '  ' "4Et6=  9D^D< '  '  '  !Cl% nDnD!% nDD!H% ZDVID!Me!% 7DVID! 7DVD ' "4Me6=  7DVID< '  '  '  VT*( % ( %  `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$dd'`M$$P[}>Qpy4i4BQpy Q` !7NQ@[d=Q` ?Q`  @ ?=[?ŏ[Qfi#`Me!Jz` "2This atom is very close to another atom or bond."FmZu $+7qZ=r4iZ=rqpy# `H#Fm@J &7O.KUE[|izB|iz  CmV`  EOU`  F ECG BCqK4i4ByqK#`Et$ #! % %!"  & '#!  P[}>xxl6_@_ )+7c[P[[}gcfe#`Cltlx@_ *2This atom is very close to another atom or bond.xZu ,+7Z}qfZ}qx# `HxI .7PxDDԧLNIxI JxI  K JIdLf}>xdL#`Me + &% - $% / &$lflvy` (   VjCD0100ChemDraw 8.0Q[@  @@' :;<   `  3xx# $$$$2$ArialTimOle EPRINT8:2 ObjInfo;CONTENTSlTU  EMF   * XV KRp8"Arial|8v?oJJxxDxxJJxxqJxhx HTJx8wJw|Jxf4Pt XonJoJwxw:w||dv%   % % Rp"Arial"j ~D Hw2w`wj ~sDw/X(DDw/P\4P  XobH&?lwxw:w||dv%  TT'F/Ux@"5@LPEs9  TT0F3Ux@"5@LPti % &% 6 % &% (   % ( '% % %  % ( % %  TTCM#x@"5@LPMWE  TTNT#x@"5@LPe0, % &% 6 % &% (   % ( '% % (%  % ( % (% ( TT #x@"5@(LPHm9 % &% t6 % &% (  ( % ( '%  % ( % % % *RL% % &% % *RL% % ( % :% :% : TT%/x@"5@:LPMPE : TT06x@"5@:LPeo, % &% 6K % &% (  : % ( '% % u%  % ( % u% u TTC2KAx@"5@uLPH\9 % &% 6< % &% (  u % ( '% % u%  % ( % u% u TT2 Ax@"5@uLPCW9 7u TT 2Ax@"5@7uLPl0 % &% \E6 % &% (  7u % ( '% FCDIFVjCD0100ChemDraw 8.0Q[@  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$d'`L$$Q[@Ii(@J “ .7M^ُe=ُe #>ـj $Abj % B &A>? '=>sЏ@3o#`EtPz /2This atom is very close to another atom or bond.QmZU 17NmZν&"DmZU (EZU ) F *EDhqZ1iZ1q#`MeRm 3+7hq(i(hq3[# `HY 0PJ gfZ 2PQ fe[ 4RP ge\Q[ED0])B_ 67O)B_̌H)B_ +I)B} , J -IH(cQ[)Bcf#`Me^0xx 72This atom is very close to another atom or bond._4Z 9+7Z""Z0# `H`4 ;+7,ED#`Cle 8^] [Zf :^_ ZYg <`^ [YVZm*WըVZm*Wըh,Á@,y 5  FdVDMHCGRTS3*D  x (XP`5. #I ~5q6 i7 eg9 e; . /v138:<024MeH ClEtMe H `` `"`v ``     ``   Y  ``  { <{ 8 `` #G#9 `` GWArialTimes New RomanFdWMDLSKXY Ariald 0 !Et!% EϳD!% ED! EwD '  ' "4Et6=  ED<!% E/D!Me!% XEBmD! XEBD ' "4Me6=  XEBmD<!H% DBmD '  '  '  !Me!% Ef%nD! ED ' "4Me6=  Ef%nD<!% E?@ABCDEFGHIJKLMNOPQRSTUVWXYZ[\]^_`defghiklmnpes New RomanxXX$dg(XX$dd'`L$$Q[@Ii(@J “ #7M^ُe=ُe >ـj Abj  B A>?  =>sЏ@3o#`EtPz $2This atom is very close to another atom or bond.QmZU &7NmZν&"DmZU  EZU  F EDhqZ1iZ1q#`MeRm (+7hq(i(hq3[# `HY %PJ gfZ 'PQ fe[ )RP ge\Q[ED0])B_ +7O)B_̌H)B_ I)B}  J IH(cQ[)Bcf#`Me^0xx ,2This atom is very close to another atom or bond._4Z .+7Z""Z0# `H`4 0+7,ED#`Cle -^] [Zf /^_ ZYg 1`^ [YVZm*WըVZm*Wըh,Á@,y *   _1158582444>!mA. [W' [W'Ole EPRINT=?I ObjInfo@lPU EMF     TV K KRp8"Arial|8v?oJJxxDxxJJxxqJxhx HTJx8wJw|Jxf4Pt XonJoJwxw:w||dv%   % V % V Rp"Arial"j ~D Hw2w`wj ~sDw/X(DDw/P\4P  XobH&?lwxw:w||dv% V  TT+F3U@"5@V LPEs8   TT4F7U@"5@ LPti % &% s 6s  % &% (    % ( '% %  %  % ( %  %   TTHP#@"5@ LPHW8 % &%  6  % &% (    % ( '% % b %  % ( % b % b  TT#@"5@b LPM\E   TT#@"5@ LPem, % &%  6L  % &% (    % ( '%  % ( % % % *  K% % &% % *  K% % ( % O :% O :% O : TT*2@"5@O :LPCP8  : TT35@"5@ :LPlo % &% m 6m L % &% (   : % ( '% %  u%  % ( %  u%  u TTG2OA@"5@ uLPH\8 % &% m 6 < % &% (   u % ( '% % \ u%  % ( % \ u% \ u TT2 A@"5@\ uLPMWE  u TT2A@"5@ uLPe0, % &%  D6m  % &% (   u % ( '% FCDIFVjCD0100ChemDraw 8.0lV[=>ꯗ0y  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$d'`D$$8lV[=>ꯗ0yi>ꯗ0y_ -7E1^e1ԏ1ԏ %1Ԁj &1bj '  ( )<\ˏ<\ꯗ3e#`Etz_ .2This atom is very close to another atom or bond.mZu 0+7qZqiZqq0y# `HmJ 27Fm@ExNmJ *J +  ,qLi>qL#`Me /  1  3 =Sm*SkӼf|y_ 4  lV[=> px<__ 5+79#ch[lV[h[mcfd#`Clrx_ 62This atom is very close to another atom or bond. Zt 8+7DZ=qZ=qDpx# `H @I :7G Dڧ N? @I "A @I # B $A?D$L=> $L#`Me 7  9  ; FdVDMHCGRTSX*h  x (XP`5. " }{4pl5 hl6 e 8 e: {- {./0279;/13ClH MeEtH Me `` $"$ ``    h ``     ``  4 ;4  `` Gw `` GArialTimes New RomanFPAMDLSKXY Ariald 0 !Et!% rE=ɳD!% bE= D! bEzwD '  ' "4Et6=  [E嫸D<!% [E\(D!H% X}iEfD!Me!% @NEfD! @NED ' "4Me6=  @NEfD< '  '  '   R S()  !Cl% `[EnD!% `[ED!H% XiEVQD!Me!% MEVQD! MEVD ' "4Me6=  MEVQD< '  '  ' % ( % CONTENTS_1158582459<.C!mA. [W' [W'Ole ;EPRINTBD` VjCD0100ChemDraw 8.0lV[=>ꯗ0y  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$dd'`D$$8lV[=>ꯗ0yi>ꯗ0y_ *7E1^e1ԏ1ԏ "1Ԁj #1bj $  % &<\ˏ<\ꯗ3e#`Etz_ +2This atom is very close to another atom or bond.mZu -+7qZqiZqq0y# `HmJ /7Fm@ExNmJ 'J (  )qLi>qL#`Me ,  .  0 =Sm*SkӼf|y_ 1  lV[=> px<__ 2+79#ch[lV[h[mcfd#`Clrx_ 32This atom is very close to another atom or bond. Zt 5+7DZ=qZ=qDpx# `H @I 77G Dڧ N? @I A @I  B A?D$L=> $L#`Me 4  6  8  VjCD0100ChemDraw 8.0Q[}@  @@' :;<   `  3lQU EMF    UV  KRp8"Arial|8v?oJJxxDxxJJxxqJxhx HTJx8wJw|Jxf4Pt XonJoJwxw:w||dv%   % % Rp"Arial"j ~D Hw2w`wj ~sDw/X(DDw/P\4P  XobH&?lwxw:w||dv%  TT*F2U@"5@LPEs9 = TT3F6U@"5@=LPti % &% #6# % &% (  = % ( '% % %  % ( % %  TTGO#@"5@LPHW9 % &% D6 % &% (   % ( '% % %  % ( % %  TT#@"5@LPM\E X TT#@"5@XLPem, % &% 6 % &% (  X % ( '%  % ( % % % *zL% % &% % *zL% % ( % :% :% : TT)1@"5@:LPHP9 % &% 6K % &% (  : % ( '% % u%  % ( % u% u TTF2NA@"5@uLPCC9 u TTO2QA@"5@uLPl\ % &% 6? % &% (  u % ( '% %  u%  % ( %  u%  u TT2 A@"5@ uLPMWE Qu TT2A@"5@QuLPe0, % &% D6 % &% (  Qu % ( '% FCDIFVjCD0100ChemDraw 8.0Q[}@  @@' :;<   `  3xx# $$$$2$ArialTimes New RomanxXX$dg(XX$d'`D$$Q[}@i=@p “ .7E^*ُُ &ـ 'b (  ) *s|Џ|@3#`Etz /2This atom is very close to another atom or bond.mZ 1+7hqZ=iZ=hqp# `Hm@ 37Fmν m@ +@ ,  -hq$i=q$#`Me 0  2  4 Q[}ED)B_@ 6+7(cQ[(c3# `H0xx@ 72This atom is very close to another atom or bond.4Z 9+7Z},Z}ED#`Cl4 ;7G4L?4 #A4 $ B %A?d""}4d#`Me 8  :  < VZm*(VZm*(,Á,y 5  FdVDMHCGRTSw*  x (XP`5. #$ ~$T5q$E6 i$E7 e%9 e"; $T. $T/&1"38:<024HCl MeEtH Me `` #"#$ ``  % % &m ``  " ! 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