Exam_2_CHEM_39_2007_Answers - Name fly 5414/2255 CHEM 39...

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Unformatted text preview: Name: fly 5414/2255 CHEM 39 Exam 2: Epoxides, Aldehydes and Ketones—wThis exam is comprised of 9 problems on 8 pages worth a total of 100 points. Please check to make sure that you have all the pages. Please show your work as clearly as possible. 1. (12 points,3 points each) Please give the complete IUPAC name the following compoundZ. b. H QC H /J 2" Eflt’xfcycfiéd-za’zz. C 0 CH3 3 ,1. CI ’7’" dA/ord “Z 'meflf/aycéé¢xGfl¢fl d. H c? 9d 32 32: 3 \07/‘\C( s‘\Gs/ \CHs H2 H2 ll 1 O a (7/41/6253 4 *049/75’ 2. (9 points, 3 points each) Please draw the structure for the following compoundsz. a. 2-bromo~3—cyclohexenec3rbaldehyde 7r (1er a B? / “3 / b. ethoxyacetaldehyde 67% AL 0 // 4/3/44’4 " 4/7.”: "04/ c9 1/ (argyle/«€4,643 2 ‘99;ch c. 3-phenylcyclopentanone O “f 2- 3/ \I 3. ( 8 points) Please Show the mechanism for the following Wittig reaction. Show all curved arrows and charges Remember Ph- is the same as @— H H \ / +_ O C (Ph)3P-CH2 + A ____________ H C I OH + (ph)3p=o 3 3 5’? 4/ /\wa-§ ,_:> (14?; 0 g Lg —/3 ”5 éfi Q— t ’45 1 \‘Q’ 6H2 PM; ¢5 ls 1. (30 points, 2 points each) Please write the structures for the organic product/products for cat f the following reactions. The question continues on the next 2 pages. When mixtures are ossible, draw only the expected major product. 3 I a CH3-CH2-CH2 /O\ H {xi/K / fix \ / HI 2 . /C—C\ " \G‘P‘V/z H30 H erg.” ! if." H O \ / H NaOH, H20 5,1; /C\ ‘ K ”C - H30 CH3 H 403’, M1 EL x9 H H ,O \C—C/C 3 H30 0 \H flHéflffi/Qé H30\ / _ \ —. / yr /CH H 445,744 H3C a"? 0:4 . o r g\ NaCN, HCN r” fixcg H C E (9 hi (9 C I! Q: *0 A920, NH30H. EtOH / \ /‘1“-£9/*/ 9 /-~¢/ CH3 3 h H O I \ ‘1. _ WHQC—CHz m CHz—MgBr —.. ‘ “Ema/7’2 M 2. H30+ i. H2 «gay/WY? O H30‘N’C-CH3 l I —>“ (3 pH 4.5. —H20 J (1/ & CH3 9 #5 // C-CI (CH3-CH2)2CuLi \ dwflé —. 1 / k. :9 <>CH2-CH2—OH PCC /\__%é _ // , —>. v CHZCIZ <4 CM —> 4é7f"% Q9 g; fif/vég/ {74/9 lé P/‘W’e Mr??? Feéfifflc m. H El) 1. DIBAH, toluene 0 2 2. H O+ H C/C\C/C\O/CH3 _.___._§__._.____> % H, 3 H2 fir ”/6 ’5 n. + BuLi m. /-/—- (Ph)3P—CH2-CH3 g 4? g? 0% Br ' {gar/f4? *vmg 3 0. CH3 é ; 33 H o+ . n, 3 “" —.. “"0 #- K‘L «2: 5. (15 points) Please show the mechanism for the following equilibrium reaction for the acid catalyzed formation of the acetal of acetone and methanol. Be sure to include all curved arrows and charges on the intermediate compounds a. Also, please circle evidence in the mechanism for acid catalysis. b. Also, please tell how you can push the equilibrium to the right. 1' o: g H3C/ \ maéiéwm’ I: rafzflcmfiea’ ”1 74/74: /¢5/ 5,4,0) Marx/4,? 7%,: ac/b/ l5" ”@7‘ az'aaggmcg ,fl 7% #5145794»? éfla/ xv: a dc; k/fiéxfil é) %a :4?” flag/f 74?: ejg,/5nz{/w K3 fie. r/gé/ 45/ 5/5/ka M fli’xc‘m a)" z/zfifl/J flit/D A7 fame 17,77; $4? 7429/" ##c remyéaa (,2? z: agave-:7”: A. 4:115 42% excess ads/£444?) szd/Ja fogs-516%? )4: 62/537wa #21? an??? ”MAM“ Ag, a/é'ansj 6. (5 points)Unlike the preceding acid catalyzed reaction for the formation of the acetal, the reaction to prepare imines (shown below) must be carried out at pH of 4.5 and does NOT work in either strongly acid or basic medium. From What you know about the initial step of the mechanism for the formation of imines please describe briefly Why the reaction would not go in the presence of strong acid. ,c:H3 pH 4.5 fhl M C\ + H20 H30/ CH3 fie ll)! fe/ SAW #1!" m 1’13“"! NM ”er/able: flat/ngafll/e 47 45A 41/ ;%q. 4dréan7/ cdfiréa». _Z_,', ”’97 4424/ . 7;" / . [Jr/:31: 7%,62 4/77”}? wow/4 ’5'“ Fffiyéaflw‘uu/ awmr gym «MW '/'./1d ”0/ 46;: (say eke-76045 3‘0” fléc/s’ofl/WVC 4' 6A 4' Mar, (“gee/xv” wag/’d/flaf/Q/‘earé’eJ re H ag—af—“ima * __... 6? 2&9 5 \A/ 5790'” fi/é/ fax/V07— ”fit/facflj,//g Ff, R70 (’(m-F/w 7. (5 points) Students taking CHEM. 36 will be preparing triphenylmethanol from the following reaction. Please Show the mechanism for the reaction. 8. (8 points) Starting with cyclohexanone and any other reagents necessary please write a multistep synthesis for 6—0xo—6-phenylhexanal (A) o 0 H H H D ' 2 02 H multl Ie ate 3 C C\ —p__';_ \c/ C” Y H2 H2 0 k H / ,4" ”x i 5.. -~—'—"-—> 1-\ or , \J 2) ZWW (gaze paid'é ,flf’w’“ / ‘f/ 9. (8 points) Starting with benzaldehyde write a multistep synthesis for phenylacetaldehyde (B). You may use any reagents fig your synthesis. multiple steps E2 ,O 241% "-. I 0.1 GHH 3 Mike M” *9 Z 2 i #343,, + B (34¢ (\l/ \l/C-j/z 0/4 P59 :j/Cfilz IG/dl‘zq? —Kr‘ /éf’§”’"’m/ @ f efli ’7 p561 find/15 6’” I) My: 9 ...
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