Chemistry 3B - Fall 2002 - Practice Midterm 1

Chemistry 3B - Fall 2002 - Practice Midterm 1 - ._ Mt? PW}...

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Unformatted text preview: ._ Mt? PW} EB; --\. l'rr:_-; nu: flutter m t ,_ I r I :52 ‘7' I" ChemlS’fW 313, PI'E‘lCtICE Mldterm 1 - r“ VLU I! October 1; ZilliE Student Harm Student 5igm .... .. Write TA’H name nr Lecture Only: ——————_ . I’leaee write ynur anewere in the SPEICL’H provided. Write clearly; illegible nr ambiguous answers will be enneit‘leretl inmrreet. 4. Only writing implemente are allowuti [NI] Calculaturs}. GOOD LUCK! '1. If} pnints 2. 3i] points 3. 55 pnintfi 4. 3L} point}; 5. 35 ptiin t5 {1. 2H ptiintfi Tulal 180 point}; MINI‘FERIDDIC TABLE I. Prm'idc alructurca for thc following chcmica] namcs HE} points} o-aminohanzoic acid 2-phenylethanal N-bromosuccinimida {NBS} 2. Ariana-cc Il1c following qucations. lit-cry wrong aIIchr cailccla a corrcci ansu'cr [3f] points {ma} 1. {a}. |L'irclc Elm: a ayatcms that haw l'n'c molccular orbitals m pointsl. F“ rm ‘3' II 1.2-“ A i.- r; foal M {flaw LI lb]. Circle lhc compounds lliat arc aromatic [a points]. I film L'l II _' H H 'I-Ir "'t’l TX? fol HR ’ I” m i "i i r l l i l it: i. Circle the compounds that are anti—aromatic [6 points]. II I' [a H H I. KN fax N f j I a I I I I "M. RN _ ..__. _ H I planar _ planar Planar {d}. Rank the compounds according to those that would react most rapidly with Big. Fefir; to those that WL‘tLllt‘l react the least rapidly [1 = n1nstt’apid.5 = least rapidl to points}. ’. C1 N02 Hill/k0 IIEt | i“ ' ““ f . _i.. l ltd-3r." lt‘l. Rank the following cations from most stable to least stable |] '— most stable. 5 ; least stable] to points}. “Ff/Ah“- Wa‘ a r'. - _ II [4' 3. For each of the following reactions sapph- the missing reagents or major organic product in the space provided. Jt‘no reaction is expected indicate by HR. [ill points totalt. l | Me at Half? | Me - I I . . I'HcI an 3*- {ai W] ' - ff La»! 2.H2O,s"i “I ill ——.-' Fl" I I q . Kh/ in} “f I M {Cl} {9) GHEEHZDH —_—1-- [under therm odyna mic, control. Le, high temp} CHgCHZOH [under kinetic cantrni, 1.3.. low temp} {'1 .';,..r Ii... " 1.- Ill- 1' 1‘: |:‘.'-.' _— If”, 1.: .I | -r ' that -,-H.s» r.. :ll .. fly | u.-. -| ql I L 1 J In] Il‘ill - H fill! II .'Il F __. r :- '-.. E J: | “Lu. r _.-—.' ."' l- .u I _ .. L_ I J 1- A .HEPp... {J} 2. Huang. H3804 I w H t-I':" 4- it (kt arty; l-- I. (“ll -' . . up .:| 1', .. ..I1.-«-I.._.:.-I .I'.‘ h'. -- t_ p""-- i'r- LE" 3. EUpatntstata]. w .~|,- .} I : ~ ' H t ' ‘ . _ . -' . {at Shm't' an energy.r lut'ei diagram fur the nmleuuiar urbttals DI the eycivpmpeny! antflrt drawn helt‘nt' {1 t} paints}. E} {ht Place the electrons in the appropriate maleeutar arbitats. Utter. the eleetmn ptaeement establish that the mateeule as ammatie pr antiaramatie. Briefly explain your answer {5 points}. 51' :Iv'i' 1' ' '- :l.l;'~"- r’fi-III': rri'i—‘I - 'I". fir-.t.aa.-Nv“tz. " * ’"' -"'*' “I LL“ |_, IA. 1'_ I'u“ [nit-rm- ._.5e~ {c} Show the energy lava] diagram I'm the ITICIJCCLEIEIF orbitals for ally] aninn [ 1U paints}. CI 9-"..er k...» II- ;: .Ifil 1M . 2‘31 _ | . ,- | r. | l ' ' ' -' F'fl—JF—‘I =EI:'——-—.-—.T_ _ E = H "I id? Flam: the ulcumm in IIH: appmpriah: 11mluuulur {ll’hitflli Is any] anion mure Htuhic m‘ lurss Mable lhun cyclnpmpuny] union? Briefly; explain your Hunter [5 points). T'J -‘ "- I'EI -' ‘ ' ~’~— ‘- ' J'--"- - '. LI"; L- '-._i I-"J-—.." fla'nJ _}'-'.-.I f. L--.{.,-: Fri-.1,” I H. *.-..4:-.a— r' I : _ " ' _ I" - III -' J! + Ira—'1 :' I-_..- .-_'-|'_-.___.. ,____‘._, luau g: _. :_._ .riu'f IQ," .- _.!.: ,. L.-- r:. -_|; Li: I L '6’; K/p' "' ' fl -" IL I "-\_| 4. Provide a detailed mechanism for the toliimring transformations {3-3 points). {a} Provide all of the monobromination prod uets for this transformation. F Note: Because NEE is solely used to generate Iow concentrations of 131‘: you may simply use Br; in your reaction mechanism {21] points). / >4“ Hes. Iw. one ———p- [h] {15 paints}. x ‘.~.'~ - __.-‘ - “F -- r’ an 1 1|. - I/"T'; — rxfiri‘: ' (J| ,5 x .J-l/ H300 ‘ “a H30 , fl. f .“1 .. I; 1;. D r l . L F “in HF“? i.| - 4 a _____ ._.:'_' x 1/ XII 34v -L' - .3" *I' III -J 503H HECG 5. Provide the mml‘ efficier-t fiynfhefiis. You may employ any reagent-5 of your Chaim {EU {mints}. D frflm Q Cl “ml aluJJI' I l i v” * ——- w 1»! mlme a f | I J 'l a;- x ' _ _ “F LN " “— 4. r_’T—" r N*1f/H-- I. 5 5—_ f, __— —V W H '|~.n,."11.,_ 1"be "f - ,H ““ x FF--"v 1 1I HI. ' .J L 51:11 . I. ...
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Chemistry 3B - Fall 2002 - Practice Midterm 1 - ._ Mt? PW}...

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