Practice_exam_2_Fall_2004

Practice_exam_2_Fall_2004 - sfimjwr’ fies...

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Unformatted text preview: sfimjwr’ fies: 5>2>3>y>sf ) 1. Arrange in order of decreasing basicity ( \, Take accountéfiresonance structures!) . ‘ CQHSON ‘ CH3Li O—OH (CH3)2NK A CZHENH2 2. Order of decreasing Brensted acidity: ‘ ' __ a. 0:445 H202 HfF NH33 CH3CH=CH2 02);?) 7/) 6 ‘ b. CH3000H3 (CHSCO)3CH Hac—fii-CHECH=CH2 7 f , o 3 CH300CHZCOCH3 H3C-ifi-CH20H2—fi—CH3 . ‘1‘ TM ,2 O O 3. Circle and name the functional groups. A! - ,4)? Mo aw (Cf/74711;; W int-’3: ' ‘ 0: (197496 . OH O ' O=O . CHSCO2Ll , OCH3 - 0] 0x me @ahanjaé-z m O=NOH ‘ Q—cHCN , Q—CH=O, \ OH aye/we O— OH O: NCH3 a (c 04 of amcme 4. Write acceptable structures of: ’kl a) 2-methyl-3-pentano e - i/\ we b) 2-buten .. .— I .— . , .0 c) 3-methyi—2,4-pentane dione d) acetone CH2 ,C CH5 W e)§-penten-§one? .é 4. Write the resonarice structures of/(Z;>= C- CHZCH=CH2 "t CHzZCHdHZ 5. é+ 1/ Hue. 'n o . 'r' / ‘ H —5H —CH 'f- CH CH: 'CH ~ 9- + £5 +- 3qui {ii 3 (b 3 (J -3 \. , [Waco] CH2 gay 0 o iQH ‘ t H , i K -- i . t- w W“ + 3%; 0” sigh—:15 >3:ch <er /e mechanisms including all In diates formal charges cu Jig—£52 QECHs-Efi HOCH2CH20Hwfiy-j QAEE I - I ”’23) 11% 3 CH0 =0 .+ CHJC-QCH3_+ OH; ,‘Qmfi _CH§CH3 QéflfiCHg CCH5. _ Iii/HO _ , CH: Cgcifj @i’éffijgafl‘S/f C. H‘fi‘h /CH3 1/ .— Q H= o + haP=<C —>~ cn=c\ 4- 0% +0# fl; Pa 3\G>15H*-CC”3J20H3 I, P—o “3 Cc 3330—? 193%»pr- *‘ P a ’" . CM; Cé‘j _ Chg? 671" CAL? f}! CW cw CW: —"’—-—.;# 'L \ ,wf Jfib "" if M 5y i A! a‘ PA Err: 7 Writes the structures of the predomInant Hproduc\/ oar; U‘ a. @044) + ECHSOH >- <E>T¢HwCrf3 M m J CHQOH \ , (PM H " cw C1! 0- . CgHgH2CH3flOH/Br2 (3 “(1:19 Ba. 2 3 (S) . - CR} +69] . I ' '- d. 0:0 + HENNHCONH2—L <,>: N N NC" NH; 0- H20) ' H‘ ,Cfis La 31 e. PhaP + CHSCHBrCHs-w—b- *EIL. +3113 ’19—... C, NC. #3 +— + , I. (01+ -“—-» <1 6/ DC‘IV5 N CH ‘ 3 medium h. chskné + CH3CH=CH—([iCH3 aqua“, 5:2 H3 NH leFZHzl: CH5 0 .. cfla Ale] HNNH . ‘ > ,, _ - —- v i. CH3COC1+ —3> .—2——2> CHéCH2fl< CD ‘ (<19ch 5%b _‘ OH”,highT —-* j. Q—cri fl; H2NOIL /_\ -—CH= NO H 1 M / th I x ' k. (CH3)3CBr ) g 6 er @1531363 COgH 2) co2 3)H3O+ S #3 H + ‘ = x I. CHSCECNa +CHacOCH3———§- .. 3O _ CH3 C._C glib?»- m. ‘ __ 1 I I ‘ qélj ‘ H ‘ n. I ' + __ . O—CH=O + HZNNHCONHB ~14» /__\ -- C H - N “HCONV‘I’L - 0. v - . I -, ... A P- , OH' _c:+; Ci! 3 , waHQ—Q {A 2 5 b a - I A ‘_ + / i q AiCl C 02~Oo© was 0-2 ~ 0 04; H5 uetf‘ 3 ;_ 5'...__ try—fills “*7 Na CHEHCH: 0 I a Synthesize CHscH 20H: CCHQOH starting with alcohols of 3 carbons \U/ til—3H3 or lesos as the only carbon source and any other needed reagent. CW3 CHZCH :. Haf- OHéP / *555 =5?» . * {F Wu: ”j’M/Nd/ kw ‘ CH3 'le a r Synthesize 2 using any acyclic starting product L, 5' and any other needed reagent. m5 b. 0- Synthesize CH3- from any suitable reagents using the Wittig reaction. Synthesize HEN- (‘g —CH2—C CH3 from alcohols of 3 carbons H3 or less refit/he only carbon source and any other needed reagent. +' +13 - + CH3 ' (.1443 0 +8471 “CH-3 CH3 CH9 I OH :L‘CIIJ --F—-C4{3 H7Hij ”CH; + C443 Cg 7V3 ' \U/ ‘ H2020 a 0/3, Cece CH3 <25? 72 cit/3, co Cat/3 ...
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