Chemistry 3B - Fall 2002 - Ellman - Midterm 2

Chemistry 3B - Fall 2002 - Ellman - Midterm 2 - Chemistry...

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Unformatted text preview: Chemistry 33, Midterm 2 Wednesday. November 13. aooz Student name: Student signature: —-—I-—_ 1nitrite 'l'fit’a name or Leeture Only: 1. 1r’lease make sure that the exam has 9 pages includng this one. Please 1arrite your answers in the spaces provided. A. 1iWrite clearly; illegible or ambiguous answers will he considered incorrect. 4. Only 1Writing implements are allowed [No Calculators}. GUIDE! LICK! l. 313 points 2. {it} points 3. 211 points 4. it) points 5. 20 points a. in points T". lilpoints Total .181] points MINI-PERIUDIC TABLE V II VIII Ile i . AREA-ET the following questions. Every wrong answer cancels a eorreet answer {3t} points}. A - | - '_ . -_r (at. Circle the eat‘bosyiie aeid derivatives that upon heating with metltoxide in methanol provide the (hi. L'irele the compounds that would reaet with Li AJIM to give an aieol‘iol after work-up it: points}. or a..«"'o (.1? .x’ '0 “a iii/it. f sills. —CEN ,t' H” K et: t: on; " Ni—i2 \ OEt) -— . ~.. ..-* {e}. C irele the eompounds that are eoin'erted into a new compound upon treatment with aqueous sodium hydroxide and heat t a points]. u- ' set 0 Km... ;____~I: 2k {d}. Rank the following carbonyl eottipounds from most eleetrophilie to least eieetrophilie L] = most eleeti'ophilie. 5 -— least eleetrophilie] he points}. 0 D U Q H'JiHH XLLH “AK Affiliate *“JLHMe-z lei. Eaeh o t' these enantiomerieally pure eompuu ds is heated wit it}. II for an extended period of time. Cireie the L_'_{_}_]Ith]th'td{S:| that heeome raeemie {ti points}. f_..-r-" ' '\ o o K‘s its “‘4 “j {b} {d} 1. H20, H+. Hg2+ :)--IC."I'1 It: I >—CECH E-LDA .. .1; 3" .' - ‘F 3.Mel OH 1. MHOE K,L\ 2.;uggar E3”: 3. aq ueous workup LE * “hi-E 3.Me0H.H+ £3€EL* 1. 50m; 2. EtECuLi Jam-4 .é-tf 3. Fm each ui'the 1" ullmx-‘ing reactinnfi supply [he miming magents or mflj or organic product in [hit Hpace provided. If no reaction is Expected indicale by NR. {fill} paints total}. J 1.03 “‘3‘ E T 5 -. 2.Zn.AcDH x" __ '- 13.,er 3. CFECOSH ‘3' 1. m2. NaDH. H20 F". D .-~—._._..-"I"J-' J {i} i NH2 )1 in LR” 2- H' a“ .sieves 1. CHEN? :f; D 1'31 F "4 ! g m ,JLDH 2. LiA1H4 Elm m' 3. aqueous work—up 0 Jill’"' ’L'ULJI 1- I all if 3x .. {k} 40' :33 2. 30m? . 1IIIIII .:.I.‘_,f‘\'_,f\11_.-.:]f_l.. f, D d 1.NaCN l .f‘x H Ph Br 2' HAWCHECHECHflQ]: Fax/“m " _-..__ I .,-.l..l;"_\_ -J .__-, pain-“Haw .a. 1h}, flnllrmmg manic-1115 LxLensu-cl} used In the 33111116515 of [he nnpormnl class, nf'nmophure anubmtms. Prom-flu a meclmnimn {2U poinm. MeDH. H+ “f '-. 1 fl L l I x f a .afi-x. ,, H —-—|- HO 1., w. H a f, a by” D OMB 3 + " r” -.__-I If“: I r I‘M-x" '“' ——? - 1 ._ .F- |- “ ““fl ’5“ L ‘J’ I .-. -"'u""---»"".""“ It. I‘ -:—~ .2 ; _1.’ :l H. '1‘] PHI“:- ‘7— M Chill-a ” h} I ‘ l {in f L" *' r - w 2 i — h",:_‘_ , (“ME-f I ' a, I r . dL _ 1 “1..., ...-' "- .. .r' x « I r Ii l {It :f? L - _ ___F,e/' ' 1." O I” I: r " L»? I pm pm ..;- H} Ark—Uni .-\ ED—hgmfi - ""\ gi‘l -- a w ."-' H “a 4—H)"- 4. \ ,h-J “Ah 1 i:- L—r—"l- ‘ II rt". 5’ ‘14'; "a.-. __~* u ' '3' fl" ' R. .Hfi I.I E}; .“r a. 4. Draw the pruduuL of the below transfermatiun and sshnw the mechamism fur its fol-1112mm. Make sure tn provide a 111cchani5m for all sitar; n F deuterium incurpnratinn {20 points). 5. Prm-‘ide the must efficient symhesis. You may employ any reagents of ynur ehoiee {it} [mime]. O OH Cl C) Rajah ,th Nxxlh frem 3 equiv 0f "HEX-Jim T H DMe A, I/__ 4'“ ' :d '34" _ Ix menu 9 “2-” L'- ' " \Afiw ';._r._;__) “fiTw LIT Kan-A"'1]"J\" [ctr H : L'.p-.iaU-'*-‘«T'-.. ' 9 .. 1 + 9 "fa .v . H._..-' "':'[-‘ —-—-—-:-?I \_/J‘-..1;_ "if! ----- —-“' ‘---.-._.._:_ I. I _ 1 DH ‘ 6. Prm'idc the; most cffiuient S}'I‘IIhCSii;~i. You may employ any rcagenls ofyt'uu' chuic: {Eli} pnintsj. O O ' V I "NMeE from r J and anyr Omar reagents D R/ "- .i'H. .-l Flu-r; H. i _ _ L4») _ _’ 39' ."f- _._ _.-*~...r"'h""' -. A , . ' I I} I' , ac: _ "—3 “I “V” “’1‘51 g :24 k “'7‘ 22' fl 9.: ,Jl I _ 51gb 1wh€g --—-“" "-1i__rFV‘-‘NH_.H"N-\. “J '- 4 j < L I, 5; H .I/ I. {a} The molecules drawn heIoia. are key building hlocks in the synthesis of many psychoactiye drugs. Circle the compound that would has e the largest ch tor hydrate formation. Provide a brief explanation for your answer. [5 flojt‘ttsl. " o - . Ital ex '- \1 i i J O L» x! kin F'h V {h} Circle compound below that would have the largest Keg for hydrate Jorlnation. Provide a brief explanation for your answer. {5 points}. ...
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This note was uploaded on 05/17/2009 for the course CHEM 3b taught by Professor Pederson during the Spring '08 term at Berkeley.

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Chemistry 3B - Fall 2002 - Ellman - Midterm 2 - Chemistry...

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