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Test_III_3331_E - I NOMENCLATURE[12 p13 3 pie each Give an...

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Unformatted text preview: I. NOMENCLATURE [12 p13; 3 pie each) Give an acceptable 1U PAC name for each of ‘he following compounds. Be sure to Indicate the stereochemical designations where appropriate. 2) HO\ 1 / ’4‘. ‘V'J R. —~D ‘6 1': 3 63' _' I / r' K, ‘ J ' lg . [If /’f\ _. - ‘L i L. 41 A h J/ '- A J m- . :I \\—"___,__I ff}; \< {195 .2, Cl— ll. FACTS: Total z ‘15 points 1. Place the following compounds in order of increasing frequency of the carbon — oxygen bond stretching vibration. (1 = lowest frequency. 3 = highest frequency) (3 pts.) Actfi’l‘e ‘0 conjugate? OF doublf o / Sight 7 0 / CH3 CH3 CH3 + l + + | I CHa-CfH-fiH-CHe CHa—CIIHEJ-CHa CHE—CIL—dlj-CHg " CH3 OH CH3 OH CH3 F95 onal’lCF |_'—l 7%Flace the following anions in order of increasing bachity. (“I : weakest, 3 : strongest base) (3 pts.) H N” ' s o n n n CHn—CM _ OHS—CE _ CHa—CH O O 0 more bfnble,‘ diabel the oair of molecules as identical, enantiomers, diastereomers, 01 SU'UCIUJL. .aUIHUlb G H H ______.__ l . f a ”re \_.. W _________ e,- we 5. Place Ihe following halide jest reactive). (3 pts.) “.Hchon=cr~r2 5 in order of their increasing reactivity in the Sxfl process (1:Ieast reactive, 53’ I?” Cchch =CH, CHRCHCH=CH9 6 Circle the alcoholls} that could be cleaved by periodic acid {l-llO4). (2 pts.) 7./Draw the most stable conformation 01 1he compound below in the box provided. (2 pts.) HECVNI : \CHa Ill. REACTIONS (40 pts; 4 pts each) For each of the following multiple step reactions. draw the Fine! Major Organic product. or necessary reagents, or starting material In the box provided. Be sure to indicate the Stereochemistry where this is pertinent. You may place intermediate products bel0w the reaction for partial cerdit. - ‘ 1) PBra 1) 2'} Mgrether OH --—-—————-—h-— 3) O:< 4] H2504. heat 1} NBS.iighl ._._._..—,._ 2) CH30H 2} 4} 1} KMnOJHGI/warm 2) NaBHy’CHaoH ’? fl 0 ” HHEG Nae 6) \A -——-- -‘ / 23 Hgsowgsowzo .a—«—-.-_...._..._.—_..._.._._._...._._._ 1) BHyTHF 2) HgozmaOI-Jmao 7 8) W 3) Cr03'pyridl'ne'HCr _________* IV. Mechanism: 10points For the following reaction propose a detailed step by step mechanism to explain the formation of the product. Show all intermediates and formal charges and use curved arrows to indicate electron flow / 0:0H2 “W (3H3 —__——-——._...——_._.-..-—-————-u——-——_H.._._._.— V. Synthesis: 10 Points From aikanes, aikenes, or alcohois of two carbons or iess, any oxidizing or reducing agents, and any inorganic reagents. synthesize the compound below. Ellr OH i CHSCHz—CHuc—CHS CH3 4‘ GROUP RAN . A. Alkyl C—I-I (matching) ‘ 2353 —2962 Isopmpyl. —-CH{CH3]3 1380—- 1385 .. and 13654370 {err-Eutyl. —C(CH3), 13354395 .L and ~1365 B. Aikenyl CHE-I [stretching] 3010—3095 C=C (stretching) 1620 21680 R—CH=CH3 93541000 and 905 — 920 RZC=CH2 (out-of-piane 830—900 cis-RCH=CHR Cfi‘H mamas) 675430 :mm-RCH=CHR 9604175 (3- Alkynyl ECHH (stretching) ~ 3300 CEC (stretching) 2100—2263 D. Aromatic Ar—H (stretching) ~3030 Aromatic subau‘ tution type (C '— H out-of-plane buildings) Monosubsfimted 690 4'10 and 730 —770 -0 Disubstirutcd T354170 m Disubstituccd 680—725 and ‘ 7'50— 8 I O p Disubstituted 300—860 E. Alcohols, Phenols, and Carboxync' Add; 0 -- H (snatching) Alcohols. phcnols (dilute solutions) 3590—3650 Alcohols, phenols (hydrogen bonded) 320073550 Carboxylic acids (hydrogen boudcd) 2500—3000 F. Aldehyd es, K000 Des, Esters, and Carboxylic Acids ' C=O (stretching) 1030—1780 Aldehydes I 1690—1740 Kctonca 1680“ 175-0 Fmrs 1735—1750 Carbcxyliu 0,0003 IUD—HEB Amidcs 1630—1690 G. Amm’ as I NfiH 330003500 H. Nitrilea CE N 2220 —2260 mmNSL'l—Y' {in—5) (a) (5) (H1) (5) (m) (V) (S) (S) (5) (SJ (5) (S) (V) (V) (vary 5) (vary 5) (S) (9-) (vary 3) (my 0 (Sharp, 0) (broad. s) (broad. v} (S) {s} (In) On) " Abbreviations: s = strong, :0 fi mcdiurn. w = week, v = vex-50010, ~ - app-mximatciy. Vi. Spectroscopy: 10 points Carefully examine me five infrared spectra and the seven compounds below. Piece the letter of the compound m the box besrde Its spectrum. CH2 {I3H3 0 I! HO—CHQCHCHQCHS CH3(CH2]3C— OH :_ CH3(CH2)4(SEN A B o C CH3 0 01-12:er2 CHacHQCHgCE o— H 0/ E CHtCH312 G F Micrometers IL": F‘ 9‘: Ta '36: . § 3-3- .._I E 10 -' : E 33 33 1-5 1"} :. p} . .- LJ .. n _- _ r pooh-WV - . -. WU 34500 3200 230:; was: won moo moo :40) no.) [000 Micromcrcrs ’f'ratnsrnituuntc \Vuu'unurnhr: farm“) 9 :5 H's. pen-cm transmittancc wavtlcngth (pm) i r I . a_‘ 2500 200-3 I800 16 wan-enumber (cm' ‘} GEN 61"er Wavcnumbcr [cm-'1 Mitre-meters ' ' - ' . . I f""\\ . - . M/‘T' “"5; i ‘5. 4'11 -_ I' ' :___ _ l __‘ - . l _ _ _ _ '| ' I l _, l:__ L ._| ......_L :1". :5: 35:10 ,1ch .891 240-; um In 1cm 5m :1: t J .30": m rm Wavcnumbc: {urn-1) ...
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