CHEM24 1. ClassiS'the reactin type fr each f the fllwing rganic reactins: H (Ea{aqa.f.'rfl''n t.--? : -.^-A (eqrferflge''rgutt. # /V T". m'y'lahm"l # ^2H-?' Lirrfi,na{t /.;A.. -^:.A 'rsr" w f' >'v"'tl! w H-cl 2. eak the indicated bnds in bth a hmlytic and heterlyic fashin. Use curved arrws t illustrate electrn mvement and draw the expected prducts. Fr heterly'tic bnd breaking, there are tw directins the bnd can break. Draw bth ptins and circle which is mre likely. hrn"t u -/ ry, t " ( ",,".f 6'6 fhr: rc) heltqlf,,c -, Bll"""u Y,#3.,&i -,r Xu-r *" Qh/ "cl 3. Circle all Electrphilic sites in the fllwing cmpunds. @r (e1fic{1cl A@ ef' -^--&' z-,--{&, C 9Yft,r.ACL Circle all Nuclephilic sites in the fllwing cmpunds. 6.4) ^,' ) fhacl --) ftt,, ( b f e?n11,nc - {,- yty'r-i1t?h/s u t ", l-'.j humiltc- il[e",&-,6 -E1- --,ft q. '- ryb ---@ ) q',.*rn"- "YJJ,il
CHEM24 5. Rank each series frm mst reactive (1) t least reactive Electrphiles: (a) Fa Ana' v, - i A ^A 3 L L @-H ( f,rrr r:cte$) '^=A- 'a' (G-5rv*tc< r'lr"vj*d) (b) B'0 7m Rank each series frm mst reactive (1) t least reactive Nuclephiles: (a) / 1 5 L 3 6 L /'/ qb'l ----fl-". -^-1., --' "., 'H Z:fl'z T L,^>" Z,Aa i l l? q..pf c-j 1a trtkr tt./i-'v (f,r nt,,) (b) A*, 4*r, F) 6 j 1 dentify all electrphilic sites in cmpund A and all nuclephilic sites in cmpund B. Predict a prduct if A and B react with each ther! "'l.l A 4^"" L tl A' - ficqe rrnc; rltr/ rdtiil(.. cmpund A cmpund B n'luihqbu {afi'vb (*tlr,-$. n{{t r) ryt H5 v^e>* t1d g ai
CHE}i.24 Fr each f the fllwing reactins there are three/fur pssible pathways fr a reactin between a Nuclephile and an Electrphile. Draw all three pathways including curved arrws and structures f prducts. Then, rank the liklihd f each f the three pathways. (a) nr- H 4 pathways cl (b)..*'.-y' H 3 pathways 3 pathways (f) 4i-, 3n #r -, /---- 75[5-?rr l->!* rfc A*, Ī 1 nly cnsider these nuc's np ch"r;r ule*i*/, lt V7,,nJ cd9rl i*i, 'f,,/-,, afi- T, rl A/-?y-J;l; *4ry r lart Z'7 7a^u- * crildrl.ulj i. ( g ^-----1., rt.il '-l (t r>, 6.fr r s.,l t rlt t rj.,'/ -ll_-).n ^l -j/ ; 7N!7 1 L btrl tt-r1,trtlx Vryl tc) { " t n tl--r 1-[1!t]L, Z f=r n,.t tv)u( L*?..t i / A 't1! )l t -v1 1 (-. r*b!,ra; tp-*/ L gerr zn>r...{ '? t-(d-d ' R.,- Ctt, ' 5 Q, f>dr G) /N? _ >zny 3 1 1 ul(>t ).?rt,,l chul S(. g f,:r/;crt / t)j tcr./lu,et{ us,t.{9t r frt c,,c-ttt, t P?p,1,afi:P rt"b,lrzrl tw* rttt tfw fl-{aae tli le-t g. Fr the fllwing reactin between a Lewis acid and base, yu can draw the curved arrws in ne f tw ways, starting frm a lne pair r the pi bnd. Draw bth methds, why des it nt matter hw yu draw it (why are they bth crrect)? 2 2 (r, J r),v -l'-> ^, l{itr -.r* x H * b* rt ll -tl, Thr*f cn'e 1** '(eraqayltt- (c*tfr {- -tt{- Z* (cv'7t{urvn"l
CHEM 24 10. Fr the fllwing reactin between a Lewis acid and base, tw prducts can be frmed. Draw the tw prducts and illustrate with curved affws hw each is frmed. Which prduct d yu think is favred? Explain. t) rl 1,,i,/ - / t(' /t t L Cflr'-tl l / r',j'y rci z) tk Ls/ -ck{r /..z/ cl.' ll*rj t y;dry -h,-h b /rl;rt F^".1r.1. C-C rb il<"tyf tsqn"{ Ba,rl C" t ffiav'n {ra$tf L h<flec (c=e l> hr-*h/ Th*yr C =C ) 11. Predict the prducts frm the fllwing curved arrws: xi*,<- f,.---- -ll { /Vt R -------------> AA.-(?.,At).b cl z,nt F C-H -A./--",-----J P*. Arcr q"_ru 4/t^ --l( > A,
CHEM24 C=L d^ $r 6llF},,r,r;l lllfilncl??r&?rnul ALY " 57 Fllrnal - At - 12. Estimate AG fr the fllwing reactins. What type f reactin is ccurring in each step? ((u' H ----------:) H----------->l t l (, -, Ce.-.r K Ftrn Frr"c *L 1s; z' C' $r z-t L{ i'c - 111bt ltd l?r,'ru/ -/ #re"k c-6e 274 Z" C 'art T'b A&c; *tulyti*al = Ai-f 13. Draw a free energy diagram fr cnverting cyclhexene int cyclhexanl as illustrated by the tw reactins in questrn 72 (yu knw hw the first reactin ccurs! assume the secnd reactin is a ne step prcess). Assume that the secnd reactin is much faster than the ftrst reactin. Label all transitin states and draw all the intermediates. Als illustrate the activatin energy fr each step and the verall energy change. q"e '"', - z;l fi"a i t l t l t-j,^t : (tryrh,} 2tr( F;,"'-=/n J Ab#n - il1 Filnnl
14. Label the fllwing reactins as additin, eliminatin, substitutin, r rearrangement. a. CH 3 CH 3 SNa H 3 C S CH 3 Na substitutin b. Heat rearrangement c. substitutin Na Na d. 2 H 2 additin H H e. 2 additin 15. Fr the fllwing transfrmatins, fill in mechanistic arrws t shw the mechanism. SH SH
H H H 2 16. Based n the mechanistic arrws and the starting materials shwn, shw the expected prducts fr the fllwing transfrmatins. CN CN