118BWin08MT2key

118BWin08MT2key - 1. Reactions: (24 pts). Draw the...

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Unformatted text preview: 1. Reactions: (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state “No Reaction’. O A) MCI + (“\H 1% Pd(OAC)2 Mo PPh3 /\‘/\/ H B) HNO3 / \ NH2 7H2804 Kr NH1 N01 CN NE C) + E heat I of CN 6» m ’ /]\/CI § D ) AICt3 (cat) ® @ H9(OAC)2, H30+ H20 (2; E)+< O OH ‘3” F) H20, H2804(Cat) ' / SO3H 100° C 2. Reactions: (12 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemishy. Assume all reagents 11 are present in excess unless otherwise noted. If no reaction occurs, state ‘No “l V‘ 5 each Reaction’ . I heat G) I H) H' (19“) ix/‘Y )Y 40° c G) @ 0.. i W on I) 1) (H30)3C CI \‘< \ \ AICI3 (1.2 eq) 0 CI H30+ C\ OK 3. Vocabulary: (7 pts) Fill in the blanks With the appropriate vocabulary wor two bold words are given circle the correct one. ‘i’ e A) Addition of a nitro group makes a benzene@/ electron rich speedsé slows reaction. B) A reaction that is under l Qrmfl ¥ng m {C control will give the most stable product. C) A NHZ, OH, or Cl substituant donate electrons by r e§0flqn c e. and accept electrons by in c . D) The alternation of double and single bonds in a molecule so at least 3 adjacent atoms are sp2 hybridized gives a or“ 0 system. B) A £0 Mg compounds such as benzene are particularly stable because of delocalization of pi electrons around a ring. 4. Mechanism: (12 pts.). Show detailed reaction mechanisms for the following reaction. Include all relevant resonance structures and the structure of the expected products. © Br2, FeBr3 n (D 3‘, 0) Br Q? B © : “Br ' FCBg £1? / H :6 \ +Ee9 g, (/C‘LG v (3) x L- “ Fag“! 3" \ ® ______9 I \ + H Bf i' F2313 \ ® intermediate products formed in each step. (CS ‘7 G) (D b CHSCé£-q 2) H 1., ’ $3” ’ 58) (B ': ) FeclaorAgCls CK \ _ Q’ZQ) *0 Cl 6. Identification: (5 pts). Circle all the aromatic compounds. ‘7 \Pleank Q? 7. Nomenclature: (6 pts.) Provide the systematic names or structure of each of the following compounds include E/Z where relevant. ea"; OH 115544;)” 5+ 3.‘l.§"l7~y‘cNoto‘p\~¢ha\ r l . * S A) 3315-: modem benzenol "W ° ’ ’m Cl Cl 3H5 —‘}~rxclalnm -l—k1€ir6X\/loenzfu Cl ' Br m - brow: — mire benzene. B) vbromo v3, VIM bent-ere N02 // C) ortho-(t ,1 -dImethylethyI)-(1 -propynyl)benzene - 8. Reactivity: (6 pts) Order the following substituted benzenes in order of their relative speed of electrophilic substitution reaction Cl N02 CH3 H CH ON A B C D E F Wt eack E > C.) D > A 7 bar Space =wmhé, Most reactive Least reactive 9. (20 pts.) The unknown compound A (C13H1802) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. m 2 2H 23 m m mm H 1H 2H 2H 5 1H 10 9 8 7 6 5 4 3 2 1 o 3 3H H\ \ 200 150 100 50 0 IR: 3400 (broad), 3030, 2950, 2750, 1730, 750, afid fingerprint cm". DBE=5Q§9 c’f’H @ cc=o bdonc=2§© @(H r O E) LS us’f benzcmSPk) \i o“ \ 207A: 0'" 0 r o H + C) CH; CH; "\ H ...
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This note was uploaded on 07/01/2008 for the course CHE 118B taught by Professor Nasiri during the Winter '08 term at UC Davis.

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118BWin08MT2key - 1. Reactions: (24 pts). Draw the...

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