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test_3 - R 10 numb ’1 fl IS I £5 E V lash l‘é AME Be...

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Unformatted text preview: R 10 numb ’1' fl IS I £5 E V lash l‘é AME Be sure to read each question carefully. Partial credit will be assigned where appropriam To receive full .L‘redit you must answer the: question completely. Only answers written CHEMISTRY 2212 EXAM 3 November 7. 200’? in pet: and in the pruvided answer spaces or boxes will be graded. L {20 paints.) Write the major product for each oflbe following. . I. T3Clr"pyr cmcacagcmou ——-—> l 2. Qt) CH; /CH; _ CIiRCIiECII~CT\ r CH30H .lL—a. \ CH; 0 Clio / r _ CH3CH2CHWC\ + CHEUH Flt—9.... CH3 0 CH3CH2CHEC‘HZOH CH3CH3CH3CHEGH (I31! cmmcnzmg HB'r l H‘ .ll m: 0“ H2304 heat SOC}: 173"" ll PERTH‘ {303 H‘ -——.__........__* H30 l. T51?! 2‘ gyr 2. NuCN 3. H3O“ ‘ heat {CHqCHgCHolgCuli $7”: M3LL§1 (”l-I - C‘r—LH; (DH 015143 .0": a til-l5 {:ng?¥4 —' (IL-“CH; OCH} OH {macfimgcuzoa Plzwztflzffi _._,_____—_} MIC—“LC”.- Cl‘lzq l D ' ll l {7% C C’fis 4...; ll» TO‘E'AL . {10 paints) W rite u detailed. stepwise mechanism for the follouing iransfarmation using the cuflcd~mm~ formaiism Show a“ intermediates o . -. , W CHZCHECH-fir i F’ 3 E : : _ . '._ ‘ __- A ~7 ”‘5" ”N 9—4qu CHZC'HACHAEF CHfiCJ-éLHLHqQHKCHéE‘r i 1/ I o QWhOw‘; E *T‘ = ‘ i , (10 paints]- Write a stepwise synthesis that will produce the given product from cchnhexanQi and an}; carbon compcund (if your choosing containing no mare than Two carbon atoms‘ You must include all necessary rcagcnts and intermediatts. Your smthcsis must be accompiished in 5 ships or ftwcr‘ Credit win mt be awarded for a lengthy synihcsis wiih unnecessary steps. 5 steps or fewer OH —~——-——————~> CHgCHgGH < W W13 3,. i439( Qffl 13r— \ 9"~ *\ 2;. 9%} EOE-h (Q3 cm , la 1 a 1 < rumw. DH é-m Gama)»; y {Ci-\s 1 J 4. (' I f.) points 1 Give IUPAC names for the folimving structures, "—— A ,3\_ ? . f T K tut—137‘s; cmmfigwm gout-£5 \ 2‘ I a“, i [>—'O“§THCH3 Iao‘F-mermxy e: cheFranME m. CH; QCI-Ig CH3CCH3 I 5. {m points) Wrétc a saepwise synthesis to Show haw the ibllowing diol can be prepared from the smrting ester 0 (1733 ll a CH3CZHCH3COCH3 —--——————» cmcncngccrls I I OH 01: OH T F: m u. a s - ' 5'— ‘ l ? Li—égaHCflz-élcowl ___#._§ *CHleHCHKEOCH'; l " CrHac-anN I 0H ‘ OTMS gammy ‘ Gigs.” Eng ' (H; H + r 3 914 P __, ; a I 3 CHSC‘VHJIC; CH2 3; CHECHLHKC'GIL r A 0H 0H f E ‘(mk mm CH3 4 6. (20 points) Complete the following reactions by writin necessary magmas). or the. major product g the starting Compeuud. me {:2 u Hw cuscmzcu + CHEC H301; M—n- EXCESS 0 H .4 Q—Ccmcug + NEZNH2 A“. El LAPAAI—Iar * cocnfin3 My. @cam 1, mm [ICN (13H w; £314 ' CH3CHZ$CH3NH2 CHECH3 H 3 Q + (I? Q‘ESNCHKPE Mi— Q—Cmgmg HMO , “LA fl-«O 5 l 10 points} Thiols can be pregarficl from the warden of thiourea with an alkyl halide. followed by hydmxid: ion—promoted hydrolysis. Write- 21 detailsct stepwise mechanism for this Imnsz'brmatinm using the curved-arrow lbnnalism. ’l 3. 5: Q i Q L‘ 1. CH;C'H2}'3I 4 .- ~ HaN/ K‘NH; -~—-—--——-— HEN N113 ' GLUE)“ - 1 7 V , lhiuurca “' HO ‘HZO uraa Clhanefilio! :c'. If “a“. l “um/“NH «— CH — .~—> ,. E;='5—¢H<.H ‘ r L. 5 (:ng ngr 3+ 1 J Y: I ’ H:::' L ”W: gut-+1 £1259. — szchE'" «fine KN“fi-B%"CHACH_3 H13” ( ( Hf mat—’9‘- w H-g—H 1 S i CH$CHK§H (16} points) Write Ilia simcture for the product Ufthc following reactian. D it ll CH Rccmw 3CC] (CH; )ZCuLi .’ ether ———"r 0 l I D I l CF43 LCHRCHACCHE How many signals would the product Show in is [HNMR spectrum? How many signals would the product Show in its ”CNMR spectrum? ...
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