ࡱ> "$! ,bjbj .0 8M4,(l(AAAu'w'w'w'w'w'w'$)Z,^'-'AA'|AAu'u'%h!'AY( M&a''0(]&,4, !',!'@''(, : 1. Explain why a substitution reaction (SN1 or SN2) will not occur on this substrate.  EMBED ChemDraw.Document.6.0  3. Consider only elimination pathways for this problem (E1 or E2). Two isomeric alkenes may be possible for some of these substrates. Draw both products if that is the case. Hint for 1,2-elimination: locate the beta hydrogen atoms in the substrate. OMs = mesylate MeSO3- OTs = tosylate CH3-Ph-SO3- AcO- = acetate CH3CO2- 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  3. Since all nucleophiles can behave as a base, competition between substitution and elimination is expected. Consider the following effects: strength of the base, structure of the substrate, temperature, and steric hindrance of the base, then write which mechanism is most likely. Draw the structure of the product formed based on your choice of mechanism. The first problem is completed as an example. 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  4. Which compound will undergo SN2 reaction more rapidly? Circle your choice.  EMBED ChemDraw.Document.6.0  5. Which compound will undergo solvolysis in aqueous methanol more rapidly?  EMBED ChemDraw.Document.6.0  6. Which is the better nucleophile? a. iodide ion or chloride ion d. acetate ion or hydroxide ion b. NaSH or NaOH e. CH3-Li or NH3 c. NH3 or NaOH f. KCN or CH3-S-CH3 7. Which is the better leaving group? a. iodide ion or chloride ion c. water molecule or hydroxide ion b. chloride ion or hydroxide ion d. alkoxide or iodide ion 8. Write an organic reaction to show how each compound could be synthesized by substitution.  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  9. Using arrow pushing, write the complete mechanism for SN2 reaction of (R)-2-bromobutane and potassium cyanide. Show the structure of the transition state enclosed in brackets (with double dagger) and show stereochemistry in both substrate and product. 10. Using arrow pushing, write the complete mechanism for methanolysis of (S)-3-bromo-3-methylhexane. Enclose the intermediate in brackets and show the stereochemistry of substrate and products. 11. Draw the the chair transition state illustrating the anti conformation for E2 elimination of cis-2-chloro-1-methylcyclohexane to give the Zaitzef isomer. 12. Draw the reaction corrdinate diagram for E1 reaction of t-butyl chloride. Label the following on your diagram: a. substrate; b. transition state leading to the intermediate; c. intermediate; d. product; e. the enthalpy for the overall reaction (DHRxn) and f. energy of activation for the second step. 13. Draw the mechansim showing a hydride shift for this rearrangement via SN1 reaction.  EMBED ChemDraw.Document.*+12XYwxz4    øyjh/2CJUaJj"h/2Uj"E h/2UVh/2CJaJh/2CJH*\]aJh/2CJH*\]aJh/2CJ\]aJh/256aJ h/2>*aJ h/2aJ h/25\h:j E h/2UVjh/2U h/2H*h/2+X{|}~4  $ % & ' ( R S T dh^^dh ! " # , . / M N O P Q [ \ z { | }  D I J h i j k ̹Т̋zztiajAh/2Uj^oG h/2UV h/2CJ h/2>*hA)j6h/2Uj[oG h/2UVj*h/2CJUaJj "E h/2CJUVaJjh/2Uj-[oG h/2UVjh/2Uh/2h/2CJaJjh/2CJUaJj h/2CJUaJj "E h/2CJUVaJ&T U ~  D E l m ' ( ) * X Y Z [ k v w   # $ % & 5 6 T U V W [ | } º͉ͯ͜|qijh/2UjgoG h/2UV h/2H*jgh/2UjqҬE h/2UVj"uh/2UjaoG h/2UVjkh/2Uj`coG h/2UVjp]h/2Uj;F h/2UVh/2jh/2UjQh/2CJUjό"E h/2CJUVjh/2CJU h/2CJ)[ @f,u9:;^_`ddh^^dh<=>?5678;<Z[\]`aļjAh/2UjyroG h/2UVjh/2UjuoG h/2UVjh/2UjtoG h/2UVjbh/2UjUroG h/2UV h/2H*hA)jdhA)U%jH hA)CJOJQJUVaJh/2jh/2U2  AK&*>B,,,,, , , , ,,,,žŶűűũŧŔɄhd8,jhd8,UjQh@U%jH h@CJOJQJUVaJUjh@U h@H*h@OJQJ h@6]h@ h@5\ h?w5\ h?wH*h?wh/2jh/2Ujh/2UjroG h/2UV2ABCDEFGHIJK>gd@gd?w>   , , ,,,,,,,G,,,,,,,  !`'gd@6.0      Chem 231 PS 6.2  DATE \@ "M/d/yyyy" 8/18/2009 Substitution and Elimination Reactions page  PAGE 1 NAME _________________________________ due date _______________ ,,,,,&,',;,<,E,F,t,u,{,|,},~,,,,,,,,뾴럛 h@5\hc hcCJh?D0JCJ^JmHnHuhc0JCJ^Jjhc0JCJU^Jh?DCJ^JmHnHujhcCJU^J hc^JhcCJ^Jhd8,jhd8,U,1h/ =!8"8#$% "Dd 0  # A22u2J$M9"qQ=zD`!r2u2J$M9"qQ=b e"ع_ @xXol3;>o8 q8' >HZ !AiӴi-FBUJJ !P)-pIPR TP$D^ݮ}E|@>k{o{3dEMD9"YR9^_9=Z%ݥv7c6׹ßW>&C@aNQI#U$>^=)3)v(t8D]c$Uڬ-,KבOt'|fS18byfq$Ӳd7 9JH^UK v;-ӷ|z&^Z{5VjM[\qыdrO+Ŗw:&)gā}3bb%xb'ɫWw1jnm`u<~6؛kv\0X{xlxL{CbyCby.3K4VyÅt,uF#) ?.y'3D3!~y3C.z͂׻f+̼8%qxӽ'>?房*%E޿ⱹ9߰.ڲϾJ™+#F.)ڤ(ƽܼG֧L!պՓG54>)鞋ڋr4ΥӂrѵMRG*0%ө<ٞ?% G/k)Z_ш&#Ti ^;oC mV_M+NufX#XQ})Ԯޞ\P~s'm^.N1mG4 p@Z+,+_:Q{45uBaYE9W٧Tt0Y+c ;N3gABJr{^8,|ngԜp.A}1`e"܄EOuKp]ܼ'I];{8c%=YWS>#61.%+sr_3)l9=~ \g٫~.N]gh;mQvgɒ'O]YU8_Nk aS="wm8,]8j?UBL$q~pq GqF,v?6;6g8'CV dM HC6Ɛ> Đ4dS Y-2Ɛ~ Ő4ds Y1cEE;C36MC7c@B=H)$@9M *OHPF9MqZXw0Pr@YZaHey~&&w]\ V⚓o.*>. p=.bAA@H3_;rvr01rathWp; -u< :P-:k#W,n^>]6(Oh?;t tv2E6gۤk?ľ$_K$Z--6T&XZ履|?빔̉(Uɉ/]EHfQhNILhcEmKSTP(xF/w#L󿨠8 `£XK 7Xd1lWX ]*6Zi֎ cmwTG+Z2֬M[w6 /fm~c-WoҕŢ+ V[ >2j!jBr7PT!!-5쐯2췱ᝰcwgʣۖ>v`PJPĘVPтI%F1B1!D$h4FK4!(M h9wfvgKAC{=s | OIļ 3U_>nq0V⬤Ksh!l|Q!$qlx&755fL`gW >^݅zZ!,L%,d41°6xVܹiؗp.䶴5'->3ymѴ'/e93u5<6mͧ}nJ)uӔI=ΘU`* hTcXHÒ&}TJNi>7X߯ y2}P梴y3޶Ng%%Π~8+)qN/Mj 럊{ i`bKJwROw< M9Σz8=ې3g:|?<= "$`"!YgoYT_y+çgХH }b^%wAwU`>ѡҵٰ<&ǩ#2:]0˦wX"h >6)mn.߈HG! ^Ob΍ #;S(ϳc\F.Zn[+# N\k`Qpl̕ә}|uU4T)dT,,YQ`/}{RPJr. Nqh2Wpʓ",=#,E`W8ؖ XP'rALgA@U,9clZFh}1DyhBi L ;Y[Ź2*M L:Ule6[1MSsAVe _+HɳjAJ,H R,H $lAВR %.)ENH !΍YNHtLBD1vTr~ ݀99hϯd-]]©U(\˨RRŽ*FP&M0GJ!%SSu,UQ&I̗TYkʐC#OMŦ^)2?w'6m#?S\)ƫ`@U4ې9[lzD-xR3CQn,;cD/vń DZE0biR- `z$GAU5;VZY1+a! c G/a#w+ {h$U{hT8Ҕi$<|iix(iY)[EZ2" ȵ`HrUX7i!%# bHKH_!yҨzT輵_La0^k99~#&ebM1l{0af<֮B)h(y8k tS4f$UGf!GV%ތx"?kK872_MϘֹXגaDl8?@ABIEFGHKgsLMNOPQhSTUVWXYZ[\]^_`abcdeflijkmrnopqtzuvwxy{|}~Root EntryX F( %Data WordDocumentW.0ObjectPoolZq( ( _1159204230!mA. 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