ORGANIC CHEMISTRY CHEM 237
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This 12 page Class Notes was uploaded by Carmela Kilback on Wednesday September 9, 2015. The Class Notes belongs to CHEM 237 at University of Washington taught by Staff in Fall. Since its upload, it has received 12 views. For similar materials see /class/192579/chem-237-university-of-washington in Chemistry at University of Washington.
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Date Created: 09/09/15
Chapter 8 Problem Session 121201 1 Give the structure of the principal organic products produced from 3ethy12pentene under each of the following reaction conditions HZPdC HZOBr2 C12 in CCl4 at 0 C cold dilute KMnO4 i 03 ii Zn dust CH3COOH HBr peroxides HBr free radical inhibitors Brz dilute solution of CHSOH CHC13 tBuOK CHZIZ Zn HZSOA H20 CI I a b C J 0 Br 0 Br e LH ll f AC 9 Ab OH k Ab Q EVCEU U383 B r H 3in d Ab Br CH3 h KE i X J PC 2 Show how one may accomplish the following transformations in a rational manner C2H 50KC2 H5OH A HBrperoxides Br 1 03 O gt 2 Zn HOAC O EtOK JV CH2I3 7A ElOH Zn OH 1 03 f EtOK gt gt EtOH 2 NaBH4 6H 1 a a Hamp gab 6474 JW 0 I 0 0 I 1 H quclb or qd quotJ WW 4 quot v 390 a m a aurapr SW Mquot u cu up Hal U u S l 5 U 1quot mi YaLab db gtQV 3 0 a 0 lt a so quot 0 AI Cquot e Inquot 4 H quot quot50v 3 H H WIN A y 7 CC39 2 CL I I I M71110 raw N13331 HSUI 9 a W 39 s M 16 R0 E 9 dfti pigI lW acme 39W 9 1 Ila Hm X J 1D 0 Law s mo cedeW C Ii 13H Ho M 05 a I 4 39 lccl 0 1 0 Aewm a El Mmm WM W Wane G 6 Aydfa h W39km my M k T 0quot LLCZ39WHI CI fn m39pd Can Jam 1 go a a39 u nA o up gamma 0 ll l 6M eM39l Mm koH MOIlint Hg M13L U WM EMF3 OZJJI fa lm Htrpwxw 39 AM th bv MCI 711 I WWW ll 060 Hallg M5 mwampuhmm P222ng H Ray MK auuw1 Jain rawquot m g m M ItoTF4 lt 0H 393 P WP W 6quot 939 K 0 ma malb39vlb w p om m 1r c g c I 4 WNW or 3 66 H KJ N c r I w W MD gt2 Ar 4 V6 75 a n gt53 of i Log 54141 Mu 5m4um 541 mar al Syn any 39IYAquotamp quot CU Wm M rm 0 1 ch apbduv LH Ina de g H szquot anquot SW 001 zs Matn MH 7T Complex Kbwl Sfmnf my ao39d2 okw lj rm I o 4 J J59 Seclir6 I 3 am a aquot 6m Chapter 4 Page 6 of 9 Carbocation Structure and Stability sources of stability inductive effect 7 hyperconjugation Thinking back to the ROH reactivity ranking fastest III gtII gtI gtMeOH slowest Reaction of Primary and Methyl Alcohols with HX Example Step 1 protonation of ROH this step is the same as in the SNl Chapter 4 Page 7 of 9 Step 2 nucleophilic attack of the ROH by X39 Reaction Rate depends on the slowest step of this reaction in this case the substitution by the Nu Other reagents for converting ROH to RX 0 SOClz thionyl chloride 0 PBr3 phosphorus tribromide Synthesis of RX from alkanes RH X2 gt RX HX reactivity of halogens F2gtClzgtBrzgtIz Chapter 4 Page 8 of 9 Methane Chlorination initiation step Step 1 Formation of the 2 chlorine atoms propagation steps Step 2 Hydrogen atom abstraction from methane by a chlorine atom Step 3 Reaction of methyl radical with C12 Structure and Stability of Free Radicals Example nitrogen monoxide Heterolytic bond cleavage Homolytic bond cleavage Chapter 4 Page 9 of 9 Carbon Radicals Evidence for the stability of carbon radicals bond dissociation energy BDE Halogenation of Higher Alkanes I 7252058 I ca M g 6 quot I I or ML PM M10 397 lll 6 SydJle M B qc knob Mohme quot I cladM MMquot know 5amper J rowmzwy quot quot3 A 4 d 0 C13 C11 d gv 9 39l Lg rjwjf l 461er W iy Cons Vqliuaa imw quot4 039 a 39I A All Mobd 46 4M 0 50A we u o m39h 0quot H a quotSYAUWIHH quot an 39 quot WWW l ykogawhm 00 H A L I L o fopbc w m AL I Salemm 002 8 High C W Oz C46 a OZ Ian L H T x v 5quot M wuva om Mx IL Shite 39 me zfm hL LA 7 m 39My 1 3h quot 0m 15 m SLIM 0F 1 AM 50L OF Lag H u c Ou vclt H u H I l u u a u l I I a I 39 7 w m m M Pf f4 9 f quot69quot 9 3039 l 54 Y 4 9 J H i 39Cc 66m 60 1395 4n inkMAM roamamt we p ng i Esme Pew 6m V39h red 1 Sh me m I WM La 3 16 6390 15 an Cf q I I NP VIlbquot Wings 1 m2 WW7 oz mu Q C 8 C 1 inkMm M 03 110 day 0 W YMM m 0F swad
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