orgo1_review_exam_key - A Nomenclature Total = 12 points...

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Unformatted text preview: A. Nomenclature: Total = 12 points Please provide a proper IUPAC name for each of the following compounds. Include stereochemistry where appmpriate. 3— ((1.93) - \ 'ma'h3\«1'pmpyry\> phenok [he-0.91 f ‘3' (lgflpyW‘) W;}LEL 3‘. 93:1!" \ 3* (My L— wry. 2' pox-g1“? U PNnni (ZFI3E>UZ'befflDOL¥-3-€h ~‘i-yn- 4 -o\ wary ocean-+6 3r:.~3—env4—g_: \Ier‘tewpaa‘._ ‘ _ 7 4‘ NOTE. MEL WEE;9‘19;?fiif§i‘?l....fl.__w,,.,_7 “em” W dzoxg M 7: WONG may r? U Keep Us 93(- - \ pem«t\»§£- 3 0 [45' fl «den—.7. \‘Jne _ 10cm,- l fi'difihfl-klhe K0“ {Ode S ’ g‘M‘r-U' B. Facts: Total Points = 22 3. Rank the following carbanions in order of increasing stability. (1=least stable, {=most stable) (3 pts.) 0 H e e e e CHgCl'b—C—O CHa—N—CH3 CH3CH2CH20 CH3 4?. Rank the following carbocations in order of increasing stability. (1 =least stable, 3=most stable) (3 pts.) H 065.. \09: / 0H 2° 6) ® HZC—C—CHZCHa CHz—C—CHZCHs HOCHz—C—CHZCHa | o l 1 CH3 l CH3 CH3 3. Rank the following molecules in order of decreasing boiling point. (3 = lowest. 1 = highest) (3 pts.) CchHz—O—CHZCH3 CH3CH20H20H2CH3 CH30H20H20H20H E 1:. Rank the following molecules in order of increasing rate of reaction with the E1 process. (1 = lowest. 3 = ighest) (3 pts.) 6,; 5 3. 7 2 7 Cl “M M w/ 25 {<22 pes of protons does the compound below have? b) What are the theoretically predicted multiplicities . Place the answers to the following questions in the appropriately labeled boxes. a) How many distinct splitting patterns) of the signals for the protons labeled a,b,c,d? (10 pts.) CS3 H H O a) types of protons I 3 I paacHz-CH—cnzchc—ig b) multiplicity of Ha n e) a ' © @562), H d multiplicityobe (n+i)(i+l)—-(3‘ziz) Q. multiplicity of Ho Lee) multiplicity of Hd ['44 i X33612 -t 13 = (Tiff-1&3): 3b . Reactions: Total = 36 points, 6 points each lease provide the major product in the answer box. Be sure your drawing indicates stereochemistry if pplicable. Partial credit is awarded only when intermediate products are shown below the reaction. 1, Brz I hv 2. t—but-O 3. MCPBA CH30H20H3 ————-— H2CH3 \(D 5. H30+ 6. NaZCr207! '42504!r CH599~043 BI\ \ ® CHFLH'CHB ) E» as; @ 1. Kl lAcetone 4‘ _.‘~ 2‘ MCPBA H CHZCH3 /\a.| \ I l L i \ /\ / . t L r L ® a k m i f .\ (9 H 0W3 .5 "‘ ‘6( @L “ ’ eaf 1.NaNH2!150°C 1 2. H30+ ‘ W 1%ng ,THF /\/\ /0\-\ 4. H202IOH' \l I‘ LfH 5. Jones Ox 0 @‘5—9\ /‘\/\(H X 1‘ 03 *1' 5. 2‘ H20 CH CH _C=C_CH CH 3 2 ( 2 3 3. LiAlethen H30+ X®® 4. FCC] CHgClz c.“ r ' (Erow @ “33‘7" _,__.__-=,» ; J Jr O CH Eu; .JHZOH V mach—L {3er 1. SiazBH H CH3 2, H20210H‘ (I: 3 (PH FL CH (EH Ci- C’H 3——" CHaCHCH2_CH 3 , ‘ O—MQBI' jaw 4. H3O*IH20 m} t CH Mr H. —<,H — 3 w 2' \ W3 9 jug p? CHscHLHl—t—H :234 he reaction presented below produces several products. Provide clear mechanisms to explain the ' ' ' ". Remember to show onl 9 co 3 o :1 :n o E CH3 firlj (EH3 9‘43 ll 025’ a /1‘ 4 ml H Q (H <//\ 4_ Vl‘\y/ qzumu3 ‘/‘Q=cucrl3 CH3 CH3 6M H CH3 ,” / " fl—nggrl 1 {OH « 0H L—‘CHCH3 {f ‘4 / / __,_3, CH3 ' \ ‘31 “ri CHM; l CH) CH; all;li ll \ _5k CH3 9 "“ Ol ‘ Q + CH3 ")\ . 0"}; 3 ¥5\/\ CHzUr—b . Synthesis: (10 points) ynthesize the molecule beiow using any of the following reagents: cyclohexane, alkanes, or alkenes of no ore than W5, any inorganic reagents, any peroxy acids, anEI any oxidizing or reducing agents. enacazcri2 W H2SO4/h or“ C‘richJCi-ifflz \/ A. " *x/ 7 JF’Nm H3063 3 ‘ ‘ LHBLHZCHI—C-U + (‘V Nggf (26w) \/ feed; '\ N‘gfeiim O /x CH3CHZQHF 8 13H \_ ,L gr \ C”2»H;caz—t—H W \K/ $30184 1 Hal/0H9 NuNHL/ 150%, EX CHgflHl' BY 4' ICEL'H 45"“ L Hit I Cl/Ha. T (12:? Aw PX CH3; CH3 8(1/ Cc \4 HQZCH; (a). Spectroscopy (10 points) arefully examine the five infrared spectra and the compounds below. Place the letter of the compound in he box beside its spectrum. CH3(CH c—OH CH3(CH2)XC\=C'H_1 CH30H20H20H20H CH3(CHflfii=N‘ x c A er CH3(CH2)3CEC(CH2)30H3 CH30HZCHZCH2PL© CH3(CH2),‘6;I =59? CH3(CH2)7C“H Wm‘mk QZL’H , £1” it. ‘ -‘ ‘ ‘. > . .. 7‘ ‘ ‘ ‘ . . r I El , ‘ . Au .. I‘ ‘ ..'_. : 47¢?! - ', !‘ :fi ,7' A r ' ‘ L'!-- - _ '__1.._‘__:__L‘_..__‘-J__L__.L_JWA_, ;._._L___1 JC'CJU 3500 5000 200!) 1800 1500 1490 120!) 1003 800 (30“ wzl-enumbcr (cm— ‘1 $00 I wavenumhcr (cm' I _\ “ZN above 2000“ wavenusnheru'cm“ I 'L .—l zkmhm 0H Shack mm *0 be LQh’TUCd 0 30mm . \{W 4 Ore 9mm sure Hey: how: a emboch w. W K WOW 63mm 1):: ‘ 6,371," - _i_5_' ..‘A.._JV:‘5.‘ ‘ ,, $5130 1—2000 m ' '2st ‘7‘ .1500 146$ “go-o. “5 non wavcnumbm‘ (JR 0 OH Eflgeci \0 CW4 \3 g: TD BOCOLm" F(b). Spectroscopy BONUS: 10 Points A compound with the formula C5H100 exhibits the IR and 1H NMR shown beiow. Please identify this compound and draw the structure in the box provided below. IDD I'IIE£%I‘IH"H'B’(EEI2t an o UN: 5’P9\+\= S-S+1: rflwggmgjuw“ £“”' _ C%-Q'Cw‘ ...
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orgo1_review_exam_key - A Nomenclature Total = 12 points...

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