Fall 2007 KEY - Finei Exam Name (PRINT) Km ms was: Last,...

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Unformatted text preview: Finei Exam Name (PRINT) Km ms was: Last, First Chemistry 3331 Signature Deeember 5, 200'? ID# Please circle class time. Dr. Bean’s 10:00 AM Dr. Bean’s 1:00 PM Dr. Bean’s 4:00 PM TOTAL Note: Present yeur student in when yen return the exam beeklet . Nomenclature: (12 paints) ive an aeeeptable IUPAC name for each ef the fullewing communes. Be sure te indicate the teleeehemietry where appmpriete. (Q 1 E- “ HZCHZCHE, I6 T @ 1 (I: I CH3 4'3 513- 4r'bTfi'i‘fla ngflTfi'f‘he 4 E r fil’htbma H /=. m- ‘1{Mei—firEmilfigcbhamem" 1 H 4;: CKKLDHWE Nu. Qhfli'fiul if“ Emmi“ flaw-Ln Eflfimre‘i , Facts: (22 points) . Place the fcllcwing carbonaticns in crder at increasing stability. (1=ieast stable, 3=mcst stable) (3 pts.) attach Owl-efl tr when {Mg 1. thiicii {sitter it we . Determine the hybridization cf each indicated stem. (3 pts) m fimi "l Ei-El’rl’liLQi {it Hi whether: H3c-—CH=c=i~i :9 all (E; E CHEE%§C:N1‘" —i H it i? ii .- "a: CHS' L “' L: M ii. ii a '- i Ii:- ‘1‘ . Place the follcwing ecmpcunds in crder at increasing acidity. (1 =Ieast acidic. 3érncst acidic) (3 pts.) 0 l 5; Lil —-‘ l, FHCH2CHz—"0H {Q OCH lg I. '6 fl CH3CH2-OH F " CHEL‘H'I“ a :‘I 3 (- 0 II R \lfi‘iu‘ EN stabilize» GU”; (-3 child 6 . Answer the fallcwing questicns fer the rlgclecule shown helm and place the answers in the appropriate cites. (i) ch many different prctcn types are present in the mclecule? (ii) Wl'iat are the thecretically radiated multiplicities (splitting patterns) at the signals for the prctcns labeied a. b, c and d? (6 pts.) H $HEH3 (i) number cf distinct pnitcns H cgzcgiélizga (ii) multiplicity cf Ha (l : i) w LfH multiplicity cf Hi, (i +2.8)(l+ 4) H $=CmH multiplicity of Hg (1+1) "' 9:3 multiplicity of H.cl (l + O) E] l Place the fellewing alkerles in erder at increasing stability. (1=least stable, 3=mcst stable) (3 pts.) cii3 .. H Eudth Gambia a bowl abridge III Cfltbfi'i‘flj was; is at "it‘lifi‘N that 'l . Reactions: (36 paints, 4 pts. eaeh) lease provide the starting material, majer product or the reagents in the answer hex. Be sure yeur drawing ndicates stereechernistry if applicable- Partial credit is awarded only when intermediate products in a multi— tep reaction are shewn belew the reactien. mien-r3 1. (CH3) car as 2. 0304: +1202 r err refit-CI? V‘- ________, 1. PBra HO "‘WH 2. CH3+CH23“ K” __._ .... __ __ H 1. NaOH I heat 2. Br: 1“ H20 OH I CH3:34-1ch05001423H3 1. NaBH4 I EtOH I 2. H2804 .r Heat 1. HBriperm-tide 2. Mg I eflwer {D / —(‘+ \._____f ‘ I? Um: war @ . 1a 3“?- / CHZCHZCHZBr 1. NaOH 2. Na20r207 ; 14231:}4 : H20 (D \> /\ .3 _ - 39 Hfifi“ 1* “30+ _ 4|- I: _ D I! 2. CHgCl-IECHOH (XS). H+ D “30 09‘3- I.“ ___'| E " (HECH3 “H '. r n fl “a HF" I 1" e r . ® I... (M; "04-15 ' . Mechanisms: (1 0 points) rovide a clear mechanism to exolain the formation of the product shown in the reaction below. Use curved rrows to indicate “electron flow". R ember to sh w onl one ste at a time. Show all intermediates and ti formal charges. CH3 _ r H3C CH3 (lg—“CH3 :HEAiH . . Synthesis: (10 Points) nthesize the molecule belew using any {11‘ the follewing reagents: aleehela, alkanee, alkenea, andler lkynea of {we cal-bone er lees, cyclehexane, any inerganie reagents, any exidizing er reducing agents, nd any perexyaeide. yet-Rf 'Y pg; RBI“ I'— EEH 77H I \“fi'C/ Elf In Wt” aw__ ....... 9 Plan HEW m —— k>fifi3m + WEJ—N \J W m ’31“ H ~99 H Fluent H309 3 "\ H-C+H_ + ear-J Tm. 3 \"x . Spectroscepy: 10 Points erefully examine the five infrared spectra and the eempeunds belew. Place the letter ef the eempeund in e hex beside its spectrum. a? EH 5% CH3(CH2)3‘C‘*NH2 U H CH3(CH2)3CEC‘H CH3(CH2)4C"0H B C D _ 0 CH3(CH2)ZCEC _(CH2)3CH3 CH3(CH2)3NH2 CH3(CH2}405N E F G H33 A we 4M1} 35M 32M! Emil} 24m 10131} 1mm 1311"] 14W 12W WW 3W EHO ' - 7 5. 5031': See me: ' .‘ ._.E,_.4I;_NH_I_._: . i ' ' : : . : - Cz‘i‘m‘fied right I ; _ i 3 fire Prime-E llpee (i’d Waxy 9} I320 EDIE flfiflfi area 2WD 24M EDDIE “DD 16W 14E“ 11E"! 1mm EDI} BED :. _.:Nmmxe - a -' i i i . . 2 fl, _' Tomi “WWW sexfiggngmfimasomo 30005 ; .biij . 11" L n..|.' — _ 'L..|.' - '1; : -_ .-I- . 'e‘! i w q ..q. _ _ _ _ _ _ :m _ fi m :m: I I -I.I.-_-_I_I_I lflfl ifififl Ilflfl I I _ . a I I I I .__|_... _.___-, _ ___ . I _ I. . I _ I . . _ I —- -'\.nl-|. ..-....I._..._-.._.- ..__._. I _._'.._. _L _ _.E I --r ... - _.IIII1I . . u u . _ m I I I I J I. -I--I-\.a. o 1 -—l _I . ., _ m -- i a. - _--_..w-. _- _n .m w a _ H I EDD 1dflfl 1Eflfl . BONUS Spectroecepy: 1U Paints eempeund with the formula CQH120 exhibits the R and 1H NMR shewn below. Please identiw this mpnund and draw the structure in the hex provided belnw. [EIEI f— SD 2 '5 Ci" {0 ‘F i 5 Ar ‘5' W“. Khaki beneeee Dlflflfl BEBE Eflflfl liflfl iflflfl Eflfl HHVEHUHHEHIflI i \ _ $33 ‘5'.“ “ H 4., CM" 5H CT ® ! [Rf 0A3 .3 i9 H 1.1 W 3.11 15 m OH ...
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This note was uploaded on 01/05/2012 for the course CHEM 3321 taught by Professor Bean during the Spring '11 term at American Jewish University.

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Fall 2007 KEY - Finei Exam Name (PRINT) Km ms was: Last,...

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