118BSpr10FinalKey

118BSpr10FinalKey - 1. Reactions: (24 pts). Draw the...

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Unformatted text preview: 1. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correctstereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. CH2N2, hV 6K1 . ’u c (anemic) “m cm“ Lindlar's Cat. M {:wmsL z (1an " H2 A) El B) K % heat /V Only): 2. C) D) O O E) f1 'l' m ‘5ngle (gourd? “77 K 1) HNO3, sto4 / nitro'z I ——————————————————> \ \ amine = 2. 2) Zn(Hg), HCI, heat 3) CH3CHZCOCI Imtnc=z NHZNHZ, NaOH, heat \Q 0 [2 (XS), NaOH (xs) />(\O kalogflhahhgz‘ Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. (CH3)3COK ‘ an“: 2 G) W (CH3)3COH Br 1)LDA H) /\ W“ 2) CH3CHZC| 3) Br2 (xs), CCI4 CN ') heat ‘ch r _. a, M, CN W’chu A} 6 (racemic) J) 1) 303, H2804 1 \. Br miSsplacd ——> / P5 5.. 2) Br2 (1eq), FeBr3 WV 503‘“! OH HIGH K) 1) P00 Mam-*- 2 2) NHZOH O ———-——> 2) CH3CH2I 3. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. If the product is racemic write both isomers or write racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’ . thflal’lw: at 2. M) X? 1) H9804, H20, NaOH (mama) / ——————-—> 2) NaBH4, CH3CHZOH o H OH eP‘WAFZ N) \ 1) mCPBA syndm’ :2 2) H3O“ 2H mum HCl (1 ) ‘ q \ eq 0) ——» _ \c’ L 40° C P) H2804 (cat) 0 O H 0 0H 0 1) LiAIH4 Q) \b —’ fi\ 2) H3O+ \) o o H o, NaOH, heat 2 339» R) )Y 2 q? Mam/Ac Br 8 r B‘hydmky 4. Mechanisms: (30 pts). Show the detailed reaction mechanism for each of the following reactions. Include the structure of the expected products and all relevant resonance structures. A) A/lkH :aOH eat > G W o of (D G) (fie 4 H10 a H <"2 [ i1 (’7 M\H u H @ 66mg) 09 “flag?” 0H o® O o O a I) fl ‘1 \ 1k e- “H NW” 2 #7 u £160“ :53 O, 4of® COMP/é)” B) VK/ 012, H20 ‘l' 6310 Cl) @ * W , G) V are” \/\V :2 35/ ’ h/EDV’; Cl “713 C10 ma ® 5. Synthesis: (21 pts). Show how you would carry out the following synthesis. Include the reagents you would need for each step and the intermediate products formed in each step. OH My —> ’1... O\ OH @ l Home” 0a,) 0 HLSOL; 0mg TPCCG) H / 99kg / Q) A @ xk \‘ T I) CllgM‘ygr‘ O/‘xb ® 13“” @ y / “301’ O H vvg ____, g a, Q) /l\ 13, *4 m D (O 043' O H 2.3 :n/Cmms -9 D)??? " Pf; 2 3° 6” l o “by 01,, ~12 Y a”); 6. Vocabulary: (23 pts.) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) At high temperatures we usually get the most stable €061 OCl’ formed this is called mrmgdy mimic, control B) Conjugated alkenes are / less reactive an mor / less stable than non- conjugated alkenes. C) The Saytzev elimination uses an UV) ndZ {GA base to give the@ / least substituted alkene. D) Generally the oc-carbon of a carbonyl acts as a good éucleophile Delectrophile while the carbon in the carbonyl itself acts as a good nucleoph’ile/ - ectrophile. E) Acetals can be formed from carbonyls using base acid both / neither as a catalyst, they are always / sometimes< never)difficult to isolate as pure ’t compounds. 0k {.00. F) Formation of a diol with 0504 and alkene will give anti addition of the new atoms, G) Which of the following is a meta director. Circle all that apply. a. @ -Br @ -0H —CH3 -CF -NH2 H) In the electrocyclic opening of 5,6-dimethyl-l,3-cyclohexadiene with heat, the reaction proceeds in a &i$ min {'1 direction. a 1) Which of the following is an activator. Circle all that apply. a. —CN -Br -COR €59 -CF3 (-NHZ) J) True False. lntramolecular aldol reactions prefer to make 5 and 6 carbon rings. K) / False In 0c,B-unsaturated ketones the alkene generally reacts like an alkene and the carbonyl reacts like a carbonyl. L) /r‘ue False. Ketones make good nucleophiles, but poor electrophiles in aldol reactions. M) Alcohols / .ldehyde / ketones / alkenes have priority in nomenclature under the IUPAC system. N) In 1H NMR of alkenes M‘ couplings occur between H on the same carbon and generally ar 0-3 4-10 / 6-14 / 10-18 Hz. 7. Identification: (4 pts) Label each of the given molecules as E or Z. Cl CHZSH CH3 H CH CH CH BrHZCHZC)\(C 3 HOHchE/ 2 2 3 HJ\(CH3 O \ CH0 CHO CH<CH3)2 N H / \ COOH E— _§_ * L 8. Identification: (6 pts). Label each of the given molecules as aromatic, nonaromatic, or antiaromatic. ¢ ‘ 1' 3H s- ‘ ® " O "I ‘ 1 1 ‘4 8 5/ w B U f c; ram non non 9. Identification: (8 pts). Match each of these with their pKa given below. pKa’s = 4.75, 15.7, 20, 25, 35, 40, 44, and 50 H O /\/ YNW W /“\OH 1—; 3: H40 m 0 H H MOH 2V JV AV 5;; g; 20 H 451 10. Nomenclature: (15 pts.). Give the proper (IUPAC) chemical name or draw the structure of each of the following compounds. A) B) C) D) E) g 0 a ‘2' 3 WH O O H T OH 240mg $1"?! 33,70 OH 0r : /Br yawn-mum benzenwl No2 Cl C 3 9 ‘ . 1%, EW: Q'GHOrav-Ll-ISopropyl '7’m0hwl-i 59.78 aim»- 7mm 44. (WM/M) . dad-5,9511%- ' gmdkyi ‘ ‘1 1m:- hexamfl. Z-2—methyl-3-bromodec—3-en-6-yn-2—ol / “0 Par \ ~ dt‘ HO / /\//\/ Br 11. Spectroscopy: (34 pts.) The unknown compound A (CHHlst) gives the following proton and carbon NMR spectra Significant IR peaks were also observed. Compound B forms afier reacting compound A with an excess of CrOg, H2804, and H20. “flunzneconqxnnkbzsandl?? "kfisggflv 50 200 150 100 IR: v 3327 (broad), 3105 2950, 2750 1715, 1620, 1209, cm'l. HA=1HJ=18Hz(d),3Hz(d) HB=1HJ=16Hz(d),15Hz(d),3Hz(d),2Hz(t) Hc=1HJ=16Hz(d),6Hz{t),11—1201) A HOWV/\ HD=1HJ=18Hz(d),15Hz{d),1Hz(d) : *3 HE=2HJ=7Hz(t),6I—Iz(d),2Hz(d), v DBE=3 =7 gigs, ‘ O O B: 27‘“ pm )VW \QH {/ a M —-7 W\4\@ leach 3 61%)); W zfiCHfO """ >47 CMJ'OH S'pt 11* OH 12 65% _ ééé “3:. ‘ b , CHlCHlCHl‘ R 3 3&5 * sh» ‘L am A: wee; gyfiwof i? “5 W+.9raJ-L ii labeled Ioffices' ,) a\coho\ +0 acid =1 29)“ Rm Qx/eh w/o SW. 10 ...
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This note was uploaded on 01/21/2012 for the course ECON 2a taught by Professor Xi during the Spring '11 term at Cornell College.

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118BSpr10FinalKey - 1. Reactions: (24 pts). Draw the...

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