Final%20Key_spring_2008

Final%20Key_spring_2008 - C\a Lll Versim I F'n L S/V?oo 6...

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C\a,- Lll F,'n{ + ?oo 6 Versim I Problem 1. Consider the reaction below. Predict the effect of the changes given on the rate of the reaction. Explain your reasoning! (20p) H3c^Br * @oa*r"11. -cHtcHto\- H3c-r'o-rrH3 + -9 "P ^P S/V L ,,E+rr,., A) Change the solvent from CHTCHzOH to DMF. 9r,, . Lt,r^ln{ l-k Jalae-"t {,.^ ^ p'a hf va}iv '-' ,\)O f" o- golon lgth. 'n''ll .'ihcrr''\' +t.e *lt lL l.tr rc--t>u, cr/e b +12 s; lu^f,>' Q'lAa'al' 4 DMF: ft:"i- bne Noo. Tta wwAnyhiit wltt bz uwo* Qffiox^t "T B) Change the starting material from CHgCHTBT to CHsBr. t ha ,t^'k t{ t\{ wo.ht- wlt( )v.,.iw. a't'( A'4 fr' \".\"^hw Sk^> t^ I ^ln *<^e- oe\ +k CK",. 9, r^"-Lh'*- ftD V,,fr-!L (CurcFrB, ) C) Change the nucleophile from CH3CHTO to (CHr)zCHO-. +tp uP;r o r< in-,c.t{r{ tt . 11. . &ss tt{ 4o-- a(qI- tte rdq wit( Jzc,**va dn* 't" 'r4^s r( b ',tL^, v,,,*<.la,rph, {t - TL. .-l i 5 , (r l* eL ra Q ,*l t( ,n'.^ct<a'!.e (;t "i*,yor l^-. { (" +1; fr*, ^) D) Introducing an additive, eg. AgNO3. Hint. .. Ag-Br forms a very strong bond. )*r l. I{" Slrr: a,, .(- ('rr.ul* ',"^tere-r' {'tt^^ 5.4''r<'e^ %- g' +I* 8f b(<ov,,.-sl arq I've^^- bdrl4L -4"""'3 '.rof Tl-e.,< f-*e F" 'rrk tl W ,<-^ohd 6'l( iwreor-' 1-* 11* fl L il-ff^;*;"'I s N L = ry = hf,',u,$rl[ u h & 1^^ h>^ evl r,r oh croofr .l'1^ .4r^.,,^-{Attf:n' + b O H^ RBr ^^o( p3'or1 c*u+*S ltu r--Q "t''il( '/ec'e'x' r. vnole 5 C\ Ul.Ar ^"( - L.\L{4L|};J= ffi fk .i' {.rJr^-'f'>^ 4 4. ]k Jr., L w it( 1.. ',-4.
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Version I Problem 2. What reagents are necessary in order to conduct the following transformations. (24p) rt: H3 81" JcHz ..-{T,r IYW"' o*" no\r,zrl I fK /n'' ?'! " P{ y Etl or HARz , fltr CHa d;-.
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Final%20Key_spring_2008 - C\a Lll Versim I F'n L S/V?oo 6...

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