PS Session 1 Key 08.26.10

PS Session 1 Key 08.26.10 - Problem-Solving Session...

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Unformatted text preview: Problem-Solving Session Worksheet Chemistry 262, Fall 2010 Session 1: 26 August 2010 Part 1: Review of Chemistr 261 1. Illustrate the maior organic product of each reaction. Circle the mechanism. - 5qu E1 E2 817.1323” Br 9 3N1 @ 21 E2 + 13:12:19ch 03—2“) 21° 00” N u" )0: + H2304 8N1 5N2 E1 52 “a? Cg am at Cal? ['1 2! ”L +- Hz ‘13 “)x —» £9 mmmeaww 2. Johnny B. Chiral, a chemist at PU, treated (28,3 -2- bromo- 3- -methylpentane with an alkoxide base and obtained a product whose H NMR spectrum contained the following resonances: 51.06 (3H), 1 71 (3H) 1. 72 (3H) 2.00 (2H), 5.20 (1H). What is the product? Suggest an alkoxide base that Johnny might have used. “I 2;} “(calm/t" : It”) ( u-l- nut) 32/ 1+ 5.2.0) :37 (I ah) (1|?) 6) ( 2.13) riflgm ' 11‘ finds?“ a 1‘! I This \9 ’h.» 'Pvuclur/l’ LU’ 21:63,; perwgnahm 09 23419“ dwm’m'w viii—2.77, fififfl'm eats R063 base was “Bi-“Z”. ”53 non 'bwnfj . 6.3, CHsoé) Na® (75) @9111) 3. Provide the missing stuff below. Illustrate the stereochemistry of the reaction where appropriate. For instance, if a chiral product is formed as a racemate, write the word “racemic” under your product. ; rag-*6”. O :3?ng H m f ’t. / ad“??— d‘m X-e a CH use. 2 0F [14/ racemlc 3 $.4de .- CenWS . O/‘V Loo/gigging) M'slmbnj 5H Mair/mt 7“”: ’f 1. Na° liquid NH .3511 flag/d! hm . 2. H26 to adjust tso pH? 0 O + 2 q H HJLH T. fi'fl'f .B‘t 1° ,3. 5' Bra. hv 4. Provide mechanisms. ”@4450“? OH ”aw?“ 0., I 1 $9 H2504 (i mullI'pl_e biggie; 6. 2/7) { I H20 slareousomers ——-——- 9% “1'0”,“ pa “2. H .9 :BI': 8):” g —-——~> H J I. /\/\>< Q/ <—-’ (Jr H1; 3‘“ IL‘3. \" 3° 0‘“- L? N “MM H33 Br 9 OM"W ' Part 2: Chemistry 262 Material 1. Provide a synthesis of racemic—2-butanol from propene, methane, and anything else you choose. 41“,” 15 many ‘h'um mun/a3 95 do 7511‘s. 17'} fassfl’Q/ID “9;, An 0.667313% Naualgs‘o, , ol+ 3”- 0 Br 0 )v :7 [05 + cusuflBr CW? 17* “5 23A \W {3/ H CthJBr Cflgar QC I'l’ RSCOOOH o ———» /</ r A 2. Predict the products. 1. 2L'0,d' thl th Br 2. 023) Ie ye er 1/ ‘r L‘ OD L; J:— A/ Drrobut'evium s 2H U @059 ‘D -® my” /I\/ *' L\ #31) KM . bgg/ ;. Mg(0), duethyl ether cl MAW” “:3,an (W L333 a ”V + R?» We wenlar \) ...
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