OLD FINAL EXAMS

NAME Chemistry 350-Final Exam May 3,2006 5pts I Wr~te a reasonal.;c rneihan~sm using tho curved arrow convention far the follow~ns reaction [Caution: all electron movement must be ind~catedlj: 5cts. 2. Dravd ttne Structure GI the expected S,J producl Idrmcd when iodldc 1511 reacts ~iith (S)- 2-brornopentane. ~YGL may use Fisct~ur '~ojections ar wcdges!dnshes to show approprlatc: stereochernrst~.] fi~ ., + C; ;;,i ,.i ,,+.! ~Ly~ddfl ~a@::[::@ (S)-2-bromopentane -. - 7 !.A - 1 - of- 5 pt, 3 Idcnt~Iy wh~ch of the fotlow~ng compounds wou[d t;? the most rcacl~he ~rl a %? react~on (1.c. LLOU~~ generate the least amount ~f E2 product ) 5pts. 4. ldcnt~fy whch product (D or E) wril form 111 the follow~ng E2 rcaction. ';tl,CH, -. I:,> ' OCH3 CH~ ,- ,Girl CKJC tiZ ./ Cti, - + L-- C or CH~CH; / A\ CH2CHJ En3 CH,CH:, CH,CHj t) / 1 5pts 5 Consider the conversion of F to G shawn below. Oelerm~ne ~f the rc;lztrr;n is an o..tidation, redu~t~on or neither. (H~nt: use oxida:ion number cornpar~sons.] OH I 7 i CH jCH2CCH3 ~i: ,' j /U,L 0 -- I I C Ci c ' 2 ii' -1 - I c, Ic. Total: -I 4 6. Which bromohydr~n (11 cr I) can be used to form epoxide J? Br~cfly exp!a~n your answer. Spts. 7. Wr~te a reasonable structure for unknown conlpound K which has the formula C:.HB. K reacts w~th two equivaients of hydrogen in the prcsence of Pt to generate a colripound with a formula CsHl:. The proton NMR of K is presented below: sp?5 8. Compound L has the formula C5lIl40 and redcts wth Ill to generate an alsohot as cne of t.~o products. The protor! NhlR of L IS presented below. Wr~te a reasor~able structure for L [Not?. thal the spl~tt~ng represents a septuplet and a doublet] 32 pis. 9 Supply Ihe rniss~ng starti~g material, reager\t(s), or mdjcr product(s) in each cf thc foliowing reactions. [In some cases, nlort! ttlan one reagent will he required11 Stu!eochemis:ry c.an bi. importan!, 5 p!s 10. Assume you were given two bottles each conta~ning a pure liquid. One bottle conta~necA compound M and the other contained compound N Explain what exper~rncnt you could carry ~lut that would aiv,v YOU to ~ilenl~fy the contepts of each bclttle [Hint: tnere are many ways to do il uslng chem~cal reactions or NMR - you need to chocse only one.] CH:, \, /' CH3CH,C- CCHzCH3 CH; 24 F:S. 11, Show how the products (on right) could bc prepared from the starting materials shown (on left). You may use any reagents/rcactants that you wish, [Hint: more than one reaction or set of reagents will bc required ] ,'%. (?I (b) ( -- - ', ' CH2CH2 <..-, ,' jiiar "-1 t+ J. 0 mcdaniel