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C8 key - rates of reaction with base One reacts 1.200 times...

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Chemistry 351 Fall2008 Chapter 8 Problem Set l. Draw all products for the following reaction. Circle the major product(s). Explain your choice. Is the reaction stereoselective? Regioselective? sfwcose\ea\iK --J€S tqp gr"d*.* tl *rr,e- - 1e5 <-,"ry*6UU .ta,'e bvored (cHr)3oK > (ro /) .- L/ + (cH3)3oH \'-----'- t , j.'. t l"tt,t^S {hnn ---'-/ . {to^s r,ore slaHr. than c.\ 2. Identify each reaction as El or I:2. reactions.l-\ A '= f')'---- \-'j + Draw electron oushins mechanisms for the followine EL ,)<' \ cH.rcH2oH ._-------------- I Az €\ c A,F"_* A vz 3. Draw all elimination products. Hzo _ acetone A. d,6-
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B. d-'' *'o-\ o rs{he yhq€ sJ""f}*U o\Lre ts fr'^d *\ggc beca-rre {t^" U is t"+ c^n\i gerig\a,'a'y Ct" +k \.*l^g O,-'f) Cq fr. $". 4. Two stereoisomeric bromides showvery different
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Unformatted text preview: rates of reaction with base. One reacts 1.200 times f-aster. Draw 3D chair depictions of both isomers. Identify the slow isomer and the fast reacting isomer. Show the mechanism of the reaction with base and explain why there is such a large rate diffbrence. What kind of reaction is this? (Hint: Only draw the chair fbr the rins where the chemistry is taking place.) Br H N+ei {his .r^$"-'\o" lorge, g,-'^g) "i9 luorn { \sov]etr ]\ rr.c+ al-H< *"""T* S-_ ,.AS -,') nry r\ in a*\ ey.o"f".'al p. .rl-l$."^ cA3 nY I ff"", (-\2nu l-br tn"r \sol{etr vJhe., J' i-" Eosifior t.^"\u'^ E. is ^*il, if x o^\i Sxtilhrar F -\&"ens. ["' {l* 9-'$"'^\ ,'Pt i "F "^h Pengta^ar, o*l fL f'"*Jt dp*. (^+;t F --bL)'...
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