2010 Exam#3 KEY - First Three Letters of Last Name NAME...

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Unformatted text preview: First Three Letters of Last Name NAME Section CHEMISTRY 236 SPRING 2010 EXAM III APRIL 2, 2010 Note: The last page of this exam is a periodic table. (24) (10) (18) (10) (23) (15) 100 GUI-RMNH CHEM 236 —- Spring 2010 2 Exam III 1. [24 points] Fill in the blanks with the correct product(s), demonstrating correct stereochemical outcomes. (3 points per blank) H C C O ) H30HzC 1)0504 % i5 0“ H|O4 A a \_— ———u _ a. Nat-1803 H20 4 H CHcha 2’ HO CH CH; chHzC‘ CIS aJclithH (:le ED 0? W‘mefii’ ameS CLLCJW‘JJE 0 leaves to b) H3CHZC\:\ M... A ECLbe?‘ le CHZCHS LA. 1-13CH2C 0H amt? vi‘orouf reaobw will not 55010 a/t'alvcoi. O H H202 VIS’V (2 equivalents) —0— C) \/S\/ gr 5N’ “We HB ' flacb‘cm d) fié—h -|- SCFM 19185 2 4 S-bc re 3:! I 1.55 E ()9 ’6! 146:,” (1+ H1 tarmac}; Bait) OHfl. ”nu Swa‘tjpfi Sulashlumx a} \J/7T4 W Mme; SWWW -2 1) L” —€U~CN Busc't’ombml/{ae’ Clay/bk Li+ —< 0H 5F- 0/ amombéuéés’l "' f) O subsbi-ubvm wt m 2)dilute H2804/H20 {we 14”“th 552er JP e/pOWEE—e . CHEM 236 — Spring 2010 3 Exam In 2. [10 points] Over each arrow, declare whether the transformation shoWn is an oxidation, a reduction, or neither. (2 points per arrow) H0 CHQCHs CH2CH3 HO CH20H3 N (:1 THe—R H30H2£f CH3 02$ l 9"“ Tie-N H3CH2C 9H3 REPUCTION 0 o (3:4on3 HO CH20H3 H3CHZC CH20H3 CHEM 236 — Spring 2010 4 Exam III 3. [18 points] Consider the following pair of reactions: HO fool-+3 2) Dilute HZSO4/CH30H OJ; Haco. OH 6] Dilute H2304JCH30H 6 (mu-J a w 2. ‘WAC'fim E a) Explain the difference in reactivity between the two ether groups in compound A. (6 points) Angle 617th of ‘Uflmemme/MEMJ I’ll/13 fluke/s (The (3'0 bone} cam ot/ZUbe/(j W (bl/101mm 17% Six *me/Wr CumbmmeeJ) ion/‘9, b) Explain the different regiochemical outcomes of these two reactions. Illustrate your explanations with correct mechanisms. (12 points) A .443 (least: WJ‘JMJ A ——7 5, (ac J chJ-st) . H+ to “yd-OCH} SWMW’WG 01F loan/471211,; at W SWLSEI-kka O '0‘”; (4f W Under least? 555103 ComoW'iJ‘nn/i 3/ \/ OHNo-rg— : MWXtflK 61627.; mmjméol: skmue, N M at m (mt HO tor—0"“: . o v smzatljfl 20 b fimd'caotabdzec} rm FIJI/©6688"; first I m CFO being“ a? tin“. Elma-(fit 3:"); fiset:néwanoi wanker Thug 1:; 11:19:55 6 Mud/1 mam? pmmmcea Mm H; {2875315 . (16:440ch became 3/3 We” . tn 5% J}I?.C— bl": Warn/End [00$ka 01494565141» dry/350?; “flailing 171%; more gwlosblmkc} 5— Jam Mamas mm demam W Mad aJt’JS W Mow: S’Nafi5hom. [Nor AN 0PM CAR BOC'A'T/d/U) CHEM 236 — Spring 2010 Exam III 4. [10190171119] Provide mechanisms for the following transformations (5 points each): 0 0 a) E Brz I SH SH N30” s~s 0 c) \ Ox/ -——9 I 3 PW S-‘H H5 '5: Br’Br H—S «5—73r’ U 1 l ' Kr k; H 6 J L? 5 53 2° Oct/EOCLLW :1?” 6M slammed 0c loam-J 3" H-mmbme) breaks {can We WW“ 2’23 ‘22?" MHz/W1 m5 Strata of CHEM 236 — Spring 2010 6 Exam III 5. [23 points] Consider the following series of reactions: 0 mCPBA dil. H2804 HIO4 H w B + C H20 D + E H20 + A F a) What are the structures of B and C? What is the stereochemical relationship between them? (7 points) .9 .3 o ”Jab $1 (18 Mame/S B C b) What is the mechanism of the reaction of A with mCPBA? (5 points) C3 0/“% I \W ‘9 o + How gal ct on c) What are the structures of D and E? (6 points) d) Explain the different reactivites of D and E with 1-1104. (5 points) , OH ® OH @ 5“) hflgmfll aw! ‘L‘Do $0” tar apart-,1 mmmé 7K/ I T " 'Qrm W Cadiz H10 J/Hrdvron f ' CH ad&“d7 W’h Hid?- rnfl—I/ng "Zisiiffivmm TMflCa/(J ”0 Maw“ CHEM 236 — Spring 2010 ‘i' Exam III 6. [15 points] Propose a complete synthesis of the target molecule within the given constraints: OWOH OH (5 0 from E: and any reagents containing 2 or fewer carbon atoms. ...
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