Fall 2001 KEY - l. NOMENCLATURE (12 pts; 3 pts each) Give...

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Unformatted text preview: l. NOMENCLATURE (12 pts; 3 pts each) Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemlcal designatlons where appropriate. 1) (3RHZ) ‘ 3~bromo~5-C\/C|ohexyl4H" ochdiene- 7—yne. ‘7 2) 3 V - a) HEZH' (arms; 3-mefiylquenfinevast-are! HO 2 CH3 ‘ f R95 Zfifchcr—iz - ‘7 5 4) .1 (12., ‘15, 65)“ 6 '53fyI-L! ~Chloro cycloackng ll. FACTS: Total = 18 points /1. Place the following compounds inborder of increasing frequency of the carbon - oxygen bond stretching ' .vibration. (1 = loWest frequency, 3 = highesttrequency) (3 pts.) - 510er “0 __7 Cohjufic‘w? 0.“ dock-M5 Gsmgic 2 3 . 1 2. Place the following carbocations in order of increasing stability (1 =least stable, 3=most stable). (3 pts.) 1/ CH3 CH3 ' CH3 1 + + r l + CHa—(§_9H—CH2 CHa—o—«c-CHQ crane-mews OH CH3 OH CH3 OH CH3 resonance r‘”_1 I 3 9‘ l filace the following anions in order of increasing @5331. (t = weakest, 3 = strongest base) (3 pts.) IH . N S O CH {[1, CH 8 CH g} 3 K0— 3 R()- 3 ‘0" More stable? . 5 ~ 1 :L AILabel the pair of molecules as identical, enantiomers, diastereomers, 01 SIFUCIUIL. .someis OH H R “Jr—“8 V” 90*” E’r will enanhc: ()1 er: ‘5. Place the following halides‘in order oflheir increasing reaciivity in the 8N1 process (l=least reactive, faucet reactive). (3 pts.) : . Br Br 1 l “H20H20H= CH2 CHgCHQC =CH9 CHQCHCH= CH9 2 :l. 3 a Circle the alcoholls) that could be cleaved by periodic acid (‘r-llO4). (2 pts.) & all N. a" l 0,. ‘\ yaw the most stable conformation of the compound below in the box provided. (2 pts.) CH3 H3c\““‘ :L/ ~'CHE X m5 lil. REACTIONS (40 pts: 4 pts each) For each at the following multiple step reactions, draw the Final Major Organic product, or necessary reagents, or starting material In the box provided. Be sure to indicate the Stereochemtstry where this _ is pertinent. You may ptace intermediate products below the reaction for partial cerdit. - ‘ 1) PBra 1) 2"} Mg/ether OH ————~—w————- 3) 0% \E/ 4) H2504, heat CH3 OCH 3 ‘ (2.) 2) 1) NBS, light ____________) r—--—-—3- 2) CH30H 1) KMnOJHCb’warm 0H 2) NaEPHJCHSOH OH 0 1) BHSITHF 2) HQOQINaOHIHEO o H 3) Croa'pyridine'HCl 9} O/OH ‘) [4480, OH #1,.“ HO O i x) 03 1o: 13 (($331; i . 4" 3)")53r-CH3 basket.) ‘0 H30~f CH fa) Hao" ‘3 ' M /0 0 m3 EFL/'13.? (ix/v x7 9)(cu3)q S W. Mechanism: 10 points fl For the following reaction, propose a detaiied, step by step mechanism to exptain the formation of the product. Show all intermediates andvtormal charges, and use curved arrows to indicate eiectron flow. 1 OH 7 O (I ‘ 0:on ——-—-> CH3 ,1 heat kl 0‘90“! ‘ I V. Synthesis: 10 Points From aikanes, aikenes, or alcohols of two carbons or less, any oxidizing or reducing agents. and any inorganic reagents. synthesize the compound below. % 9H CHSCHg—Cng—CHS CH3 T sz/Hio CHQCHQ' CH .1: IC,..CH.3 EH; In" HRSO‘i/b Fm CH3 cu;2 CHa — c; “CH3 2,.) mm “301” CH on c q 3 '1 H‘-%Br 1- ‘Cdcfi t 7 a: 3 C65 "‘13 /eulq- N Tones of FCC Q5542 ‘5’ Pg 914 f '3‘ , “as 6’6 ('4 F"! CH3 7 Q Cit; WWII H301“ C’fac 8 If f “736” r a (Hi/)Wr + “JCT”? I ‘71 T C 99% W ‘1 mJ/rfic, ‘(m @Cfi. TF’CC / '2 9r to”: P C” (W ’émx fll’f I ’5 CH7 VI. Spectroocopy: 10 points Carefully examine the five infyaregd spectra and me seven compounds below. Place the letter of the compound in the box beSIde zts spectrum. ‘ H 9H3 o C 2 ll HO —CH20HCH20H3 CH3[CH2)BC-— OH 3, CH3(CH2)4CE N A B " D C CH3 0 CHgNHg CHECHQCHQCEC— H E CH(GH3)2 G Micrometcrs § . 3 B 5883' 'I‘mng:1nnnnc:'c{%) S » 4000 3500 am 2300 24m 2000 woo woo mo um 10W 300 59° 4°” F , ‘ Micromcters 1: ‘3 4 5 6 1 - B 9 l0 H L1 13 :4 [5 m 100‘ _ ‘ ‘ ‘ _ _..|_‘_._JJ_ Tmnsminmme (7n) L. o «to seen no: mo 2 :50 no 13: :o moo mm W +0 1030 s; n too :0 Wavenumbdr (:m‘J) oh“ ' ‘ Em“ am alg‘ie‘no wavelength (gm) I416 10 Hll 9 B 5 5.5 4.5 uunu:_.Emcu: EuEun {Junumbcr (cm ' ‘3 Ca: 600 [400 i200 130A”! ancnumber (cm—J) I600 lHl'A’} DUI) 1 3'200 2 600 240-71 lr’fll’) " '30 Micromerers SS uu—Ezasmzfir 600 800 [HOD I600 I400 [inc 1000 Iii-IX) 2400 2300 Wavanumber (Carl) 0 I ...
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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 2001 KEY - l. NOMENCLATURE (12 pts; 3 pts each) Give...

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