ࡱ> Z bjbj ."   8E$i$ i.(777$9-77#77<7v(  pT90i\,4vi : Dehydration of Alcohols and Rearrangements Practice drawing mechanisms Your goal is to determine the structure of all possible dehydration products. Adopt a step-by-step procedure to answer these types of questions. Here are the steps: Protonate the alcohol to give the oxonium ion Lose water to generate carbocation Identify b-hydrogen atoms and draw each alkene produced from loss of HA, HB, etc. Return to original carbocation and consider all of the possible rearranged carbocations Identify b-hydrogen atoms in the rearranged carbocation and draw corresponding alkenes  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Draw the mechanism is code for push arrows to show the formation of all intermediates and products. Practice drawing the mechanism for the following reactions. The groups that can migrate include hydride, methanide (alkanide), phenyl groups and other bonding pairs such as the sigma bonds of a ring. 1. Draw the mechanism to show formation of all possible intermediates and all possible alkenes.  EMBED ChemDraw.Document.6.0  2. Draw the mechanism to show formation of all possible intermediates and all possible olefins.  EMBED ChemDraw.Document.6.0  3. Here is another way to say the same thing: Draw a mechanism to account for all intermediates and products.  EMBED ChemDraw.Document.6.0  4. Draw a complete mechanism for this dehydration.  EMBED ChemDraw.Document.6.0  5. Draw a complete mechanism to show how this ring expansion occurs.  EMBED ChemDraw.Document.6.0  6. 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     Chem 231 PS 7.1  DATE \@ "M/d/yyyy" 8/18/2009 Alkenes page  PAGE 3 NAME _________________________________ due date _______________ +  z | V X      < = > ? & 5 V i q r WXYwwkhCJOJQJ^JjWhUj/E hUVhWFCJOJQJ^JhyCJOJQJ^Jj:hUjt/E hUVj/E hUVhjhUhCJH*OJQJ^JhCJOJQJ^JhCJOJQJ^Jh5CJOJQJ\^J&+ > D  @ q r X{|}~$a$ & FdhwxyzPQopqry16 3ථࣛtggthCJH*OJQJ^Jh6CJOJQJ]^JhCJOJQJ^JhCJOJQJ^Jj-hUjJ/E hUVjlzhUj/E hUVjbqhUj/E hUVhCJOJQJ^JhjhUjbhUjQ/E hUV(Pstuvwxydh>?@ACDFGIJLM  !`'34:;>@ABDEGHJKMVW^_st}~ùééÆxeYS hCJhCJOJQJ^J%h"0JCJOJQJ^JmHnHuh0JCJOJQJ^J#jh0JCJOJQJU^J!h"CJOJQJ^JmHnHujhCJOJQJU^JhOJQJ^JhCJOJQJ^JhjhU h5\hhCJOJQJ^JhCJH*OJQJ^J  !`' h5\hh,1h/ =!8"8#T$% :Dd %0  # A2:fV5Vt9Dn`!9fV5Vt>'p2]X.9x]|ݽ۽\Ir H'H/R R DADDA`@Rԟ EAD" "HAZf&"O2}{3)ȉ½U@v?6+ dǥ[ܩ샫q%BD~ WjFg!v~]ScoT:a4T_WN+h"RS)`cH[\UzuQЮ\ݩ4W۵& NVh:.ȠJ-֢MV%nߘ R&F/ΐYXMVIӁg`i`aQ'µ{%~^1NZtĦwnS f/]3&&NA'd+ן&?CW V.Tx脀n.Cnڼu:5F@7b,:)ߖrx̂}pUhXw!+hI!%$4s, F"/n+& |xps˷3%v%`m^,01i_4%hF Rjp5 _S]zTE ڱvuHA@(tuIl#Y]N"K,])YJ>M&St/Y ; f/.VH R{i&)%<`Z6fH<@:.&LtLߺκܺIM!7٦LqX<lyc:y1tq+˺(VϬaYqԢH ExMTOFe[E?2F[+Ĩxe{6iZ&MMQ6E!kZvqb q$6d\uEY>;Ey'$C2ĭ ft@} ᯠUY>Y< &S^+hWwvttf]U`GfToj2f7]O=|\/?`x'4Ly&Mx\I.2 ߔ9V{^wko,B ȝy2;)**ƈ,xf[B+ȹSLDVeBU5zb˴PYF.x{M#w|3]şWefUWRٷҫmvRM1hO+6([ϳ5g N74oN+!0 3U>>hӱ[,˴5㭰4ǽ:*<}iNm`YrOi/L !jIgIo gy<}jri;[d;WkD9+Z&Hþ .{#E< ^-v75]%=yd<^t0: rzz\~9VC)`ګŶgJ47j픽ҖփL D+; hf-^"Z/E&/rf_**#,/iR:]60ZEr4ݕ EUWP z-(zEnDsh8l˚y/S3: m=٢c㭷4-pS;6̂k#x`1ʢ&cM| 7oޫ\M|S)od) a\M&cWF-Rz[{ hf^[,W)'\H";9ƟYP/zJ8AiPФ9 YFD@;KYX x̯ɔ%հRCdJd":扵KƤ*=F|XIz+rcǓbspsҿBoEgce~IY-#?)-?)YۿuFSuL6󟒎닅.=/hd̞891: R8QAGx[8pmp3D_GhDE cAd F b8bt@ Э*VLzO.z4dz]RF72473xA@)폶Sn~x~lh$bgbETF/BG<^2: xq" BOY耨Y13: VyxsFi"1: xyYFD'//,Z"fy}:KEr+/ǾRۯ" ,3OڶV\9PE HxADG8Ɉ/$ި3: 6~+A: Zxmh1Wm{UEm٣"xQ耨dR~lQ,IA73;Md(Kֽԝco`t@~F [<H= !"#$%&'()*+,-./0123456789:;@>?AGBCDEFIPJKLMNOQURSTVWXY\]^_`abcdefghijklmnopqrstuvwxyz{|}~Root Entry! 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P^( P^( Ole ObjInfoCONTENTS8 #$%&'()*+,-./0123456789:;<=>?@ABCDEFGHIJKOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~VjCD0100ChemDraw 8.0̌I 3s gfgf @@' :;<   `  xx# $$$$2VjCD0100ChemDraw 8.0O"R6 gfgf @@' :;<   `  >Sxx# $$$$20ArialTimes New RomanSymbolx,, 8 ` g(,, 8 `dd'`$$2sA'yFfL;T: 7^] 72&lf 7i*$ "[&  wt. +7w,&>q,y(:#`CH3Sx3 "[s@ +7dO^=W=B`FfL#`CH3̬Dx3 +7G02sA0H<#`OH                  SjX^Dt1W;\ 7+;CA:"t6~W;\ +ZDY_TDY/[ݒ^# `S,p;\ +sfCY|mfCY"tfC_# `O>;\ +AfCY+;fCYN8tON&` 7P%mYχ 7Q?f 7R}dQ SyUt Yoa +7Er*3k*8tԳ#`CH3[GN  ]yU  +7EXߊRZ#`CH2bpMA +7D## `He}e +7̩hfCb`3j\/An atom in this label has an invalid valence.#` HBg7vEpG 7qJG~Fj o+!Jzq{-Bz1qJG~#`@H-Fv p3AJG~{CG>qJG~ `AJ5OA5HL#$ @-HA+/jQvp =+7tjQv/An atom in this label has an invalid valence.#$ @-HB+7Aje/?} ?7 @7* A7gm BB'm¤ C{Z I+7bGAG#`CH3 KB'x M+7Tu:#`CH298 P+7ݷ@v:@# `Hx R+7 サ.}U/An atom in this label has an invalid valence.#` HB̅* U72L8w0)̅* 3A22Lv2 `Ax*   g* +!ᓷ~1{~K>#`@H-g6 3AᓷK>{-KK># `AG9ᓮ9Hz#$ @-HA+XNRONҙ%P 7%NOXNRONҙ&ChemDraw can't interpret this label.#P*trisubstituted (same as above)7Q 77&ChemDraw can't interpret this label.#P#tetrasubstituted alkene#ȊL6,'ċ 7]*Ȋ#ȊL6&ChemDraw can't interpret this label.#E?initially formed 2 carbocationO"R6̌, 7̌, 7̌ 7 7        @;33;Yt &ChemDraw can't interpret this label. 'Q  rearranged 3 carbocation (more stable)L|<   " <}?1   " <2;aPs;apY    $=N}N >  " <q=y}=y T  " <N N    x Nx    @    @@    O        2    $  +  %  /   7  7 8   7 9  C' ,OPQRSY[]beg( @+ + ' 0( @+ + _1160756596 !mA. P^( P^( Ole ObjInfo CONTENTS0ArialTimes New RomanSymbolx,, 8 ` g(,, 8 `dd'`o$$ǎI ̬` J,  7b   7ď, 7f J, 7c `b e bd g df k f` ^Y@LQvז3s  &ChemDraw can't interpret this label.UI>9+h./013 Once you look at all of the possible products, it is easy to apply the Zaitzef Rule. Notice that the same product is produced from the initial 2 carbocation and the rearranged 3 carbocation, i.e., the trisubstituted alkene. In this example, the trisubstituted olefin most likely arises via the 3 carbocation since there is a strong driving force for the 2 cation to rearrange to a more stable intermediate. It would be difficult to prove whether the trisubstituted alkene came from the 2 or 3 intermediate; however, an intramolecular rearrangement (2 3) would be expected to occur faster than a higher-energy, bimolecular process (loss of HA from the 2 cation)._1160754575!mA. P^( P^( Ole  ObjInfo !CONTENTS"B VjCD0100ChemDraw 8.0 JW޵`rM; gfgf @@' :;<   `  Upu3xx# $$$$2$ArialTimes New Romanx,, 8 ` g(,, 8 `dd'`$$% JW޵`r,&]l +77h`aYW޵ba#`CH3'] +7h`B,YBс`B,#`CH(|M +7LPB, JB Suo#`CH3)k]a !+u`JYY `J#`CH*8(] #+7с`&Y&b,#`CH3+Wna %+7Fr-E|k-`r-#`OH, &' -  '( . "') / $)* 0 &)+ =MOFYF3>RF (7oA5F pFw?RF +MUF4OFV# `S8F + <oA5%<D# `OlF +o'i pD# `ORz6 +MUF24OF2VFw?#`OHR( +MUF?4OFVF?#`OH    ,VFMOFYF3#/  H2SO4Rl`noajn.Sc( )7xgl`noajn.5This label has conflicting or unassignable charges.#% - H2ONC\8C\ '     % N = RVjCD0100ChemDraw 8.0jX? gfgf @@' :;<  _1160754769!mA. P^( P^( Ole LObjInfoMCONTENTSN^ `  Upu3xx# $$$$2$ArialTimes New Romanx,, 8 ` g(,, 8 `dd'`$$jXs ފ ? @_ Bׄ Dv FE H+7Y?/tts #`CH3lL J+785,8-8#`OH L7\ M7f1 N7\ O7 P7y6~ W7J~ X7ׄ Y7J Z7y6 [7b%E b7 PE c7  d7 P/ e7 b%/ f7  A  C  E  G  I  K  Q  R  S  T  U  V  \  ]  ^  _  `  a  g $    h  ! i    "" j   # k   "$$ l  dNJ_J_8eJ  w7oAI JCgJ  m+NJA4J## `ShJ  n+ oAD%## `OiJ  o+'D ## `Oj~: p+NJw74J77JC#`OHk q+NI 4II #`OHl rghm sgin tgjo ugk,J_NJ_J_8#/  H2SO4plpa2q x7x.lpa25This label has conflicting or unassignable charges.#% - H2OrDR=DC v      r d p_1160755201!mA. P^( P^( Ole ObjInfoCONTENTSXVjCD0100ChemDraw 8.0_WiM gfgf @@' :;<   `  Upu3xx# $$$$2$ArialTimes New Romanx,, 8 ` g(,, 8 `dd'`$$_Wi?@qi 7i*x 7@q.t iF @q] 7Z̬ +7,^P_WPeF^P#`OHfff +7fƃ2o|2ö#`CH3             ]H_h{%cH "+!7fH_]H_h{#@H+lonoaynr( #7xvlonoayn5This label has conflicting or unassignable charges.#% - H2OCkCkî !        VjCD0100ChemDraw 8.0_Wi.M gfgf @@' :;<  _1160755172!mA. 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