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Chem 112B-Spring 2006-Midterm 1

Chem 112B-Spring 2006-Midterm 1 - NAME SID GSI CHEM 112B...

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Unformatted text preview: NAME SID GSI CHEM 112B Midterm 1 February 22, 2006 Question Points Points obtained 1 (20) $32 2 (15) fl’ 3 (10) lo 4 (15) I 5 (20) [h 6 (20) 3: Score: 6 i/IOO {A 1) Fill in the missing starting materials, reagents 01‘ products: a) b) NA'S ZI SnBu3 Pd(PPh3)4 ____.> K2003 H20 H H d) N/ up“ AME}: in“ u I . SOQPh M,‘,?/cm<\~m%'v ;; resumm ADV-ml [ai‘ SnCI4 MeO MeO 2) The following questions deal with numbers. Encircle the correct value: a)_,The empirlcal resonance energy of benzene 1s: 10 kcal-mol“ 36 kcaI-mol" Wheel-meld- W . M‘. g :._ m ‘ a: b) The pKa of phenol is: I c) The bond dissociation energy (BDE) of an allylz'c CH bond is: , (lifié-EiAlrcaI-mol" W 36 kcaI-mol‘1 55 kcaI-mol" d) The chemical shift of benzene in an 1H—NMR spectrum is: —3.0 ppm " 7.3 ppm 5 2.1 ppm 9.2 ppm 5.6 ppm 9) The number of possible isomers of dibrorno nitrobenzene (C6H3Br2NOz) is: z» [(7 ,8/ ,5' & none of these 25 1.8 ppm 5) Aniline reacts with either nitric acid and nitrous acid in very different ways. Show the detailed mechanism of the following reactions: a) NH2 [Ag NH2 HNO3 I MCJ'L‘? H2304 N02 / a 1‘: “Edi Ora ., O -1 ‘9 U \‘L FM eriéN uo—N' 4 Maw ”ALMLé—NSJ ——> 0:N=° \D U o \ \ L "”1 (”wk-:3, mix (”K wk i ozflté z" m: fl; “is; . @ai, .4 flash ‘ h “51»; l Viv; we M3114 "ck-QT: ““1 5| M 5"? J‘remq at“? b) AWN“ ll ””2 NED Ole C1 We E: HCI, H20 \ J (a 3‘ 4/” \w ($3 9" - c0? _ \Lu 5_“5D 4-3! 'N’ Vin}: N3 90 —N=0 “37’ H “WM“ A “1' E. "1“ 5F" ' Nficl" I ' "”1 A, (if O‘Néj \H .K-l: 331‘ {1.4.4 8'“ =§EH if! . “:0; 0‘ N “.6 a" e «e -» e “-3 '4 41”" l ’0“\ vfi‘ 1;! MON» \ r: ,2 :5 if wry Mug-\d ...
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