Chemistry_2220_-_Maguire_-_Summer_2006_-_Exam_1

Chemistry_2220_-_Maguire_-_Summer_2006_-_Exam_1 - 1C Chem...

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Unformatted text preview: 1C Chem 2220 Examl 7 100pts Name Kgfiafl gym (3p!) Circie your TA 1' Quiz section ' SpringSummer 2006 1 M 915 STAT 111 Asare—Okai 14 R“ 199.19..” ETAL 131 Asare—Okai 2 M 915 STAT 114 Bittencourt 5 M 915 STAT 219 Rijal 3 "i" 1030 STAT 131 Rijal 5 T 1030 STAT 219 Bittencourt 1. (IOpt‘) Name the following molecules: ”0 QC” H3C—C ‘c: \O~CH2CHQCH2CH3 Z7“ 'jéfzgfim #19wa ‘ [943/72qu 6 I") 14;?” 1‘04”; V Cl CH /fi\ 6 GO 3 .9? CH3 COOH W‘Gjiflwaylaflnmg 2 _ Me @1244 (9y? )9 - rip/7 57:31? a? LI/WZW‘L d6 1%: D/ V V“ - 2. (812:) Write a complete mechanism that describes the nitration of benzene to form nitrobenzene by an eiectrophilic aromatic substitution mechanism. Include steps that Show the generation of the electrophiie. Naz 3. (8px) Rank the following molecules in order of decreasing reactivity towards electrophilic aromatic substitution reactions. SO3H , ,4 Mixing? .. ,_ QS§ O i ‘ \3 N S A D E at 3 I Q 2 (40054 >55; 1/) 4. (6pt) Imidazole contains a pyrrole like nitrogen, and a pyridine like nitrogen. Explain the difference in the basicities between the two types of nitrogen. 33 fl axiom/xxx W im n W 6.x mm m [9011+ ‘71 5/6”?! Ag” 7%}??? g'fy/ 401/ as fan/71 07C V541! Manse}; \ \5519’3’“ eff/ix rim VMD/éy? ,} (M if" préVlofiofilh’l $0 72‘ MY? imam it” fit rgrroé m6 milfaW laws in fit Miami" ”If ”drew 72; (4% far ’5' Far]! ”0% MMWJ“ '5ng (“’4' banal) 7/14/57,? I715 /55 £9).ij M£;(®a{( Lit/Aim [fir/5 yfgivnwfiaé 754‘- Wamég {NE m rm; girafff 5. (6p:) Show $1. the possible isomers formed by this reaction. H038 SOSH 505}! ”035 NaNH2 m M 5 - 7 NH3“) / N H; Br )3 . ’24? f?! + V305 :HZSOEH 4. (15m) Draw resonance structures that describe the electron deloealization in: a) pyrrole ’ “”9 f“ 37% Q? L “a. \ H . JA/ b) benzoic acid my 7. (1819:) Predict the outcome in these multistep reactions ox 0\\ / \ /C'CH3 / \ so! CE’CCH3’6H3 CI (75”.? ‘6 S AIC!3 5 P403 3 {3f \ Brz l \ CH3Li N/ 300°C N/ A HCCHS)? c Q05 CH(CH3)2 N: NH2 NaN02,HCI H+ 0°C - warm C(CH3)3 6(5ng 600 H 9.06121) Devise a synthetic; strategy for the following: a) (3 steps) K0 © cm 2%Gw 4&1; “5”: 6”: b) (4 steps) - 0H3 \ OQC/OH \ if of 1’5 3 \ \ 0 C ———— KM 4f) [/flifl; ) /—-——?A€:€3 1/6 M7|/-”-§‘l\ N L’ [email protected] . I N V N/ I w ('39 09 e) (3 steps) \0 #365 00 CW ...
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