118BSpr10MT2Key Livens

118BSpr10MT2Key Livens - 1. Reactions: (32 pts). Draw the...

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Unformatted text preview: 1. Reactions: (32 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemisny. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. $03H A) sos,sto4 EEG) CN © Cz) NC," B) J heat \@C” I NC Y ’//cN + CH 7 /. mcemfc /. Cl (1 eq) ‘ c) __f_. \ Heat db/ Cl C\/\\)¢ 2,9,3 G) C\ D) M _N..____.Bs’hv W + w A Br Z hv \ E) p ’0 “l MnOZ F) H0 / Howfi/ OCH3 a CH q 1) Clz (3 eq), AICI3 G O ) E: 2) HI ]\ @ Cl J\/Cl AlCIa \ wk ‘1‘ 'r’” 2f 2. Reactions: (5 pts). Circle the compounds that are likely products of this reaction. Of these label which would be the major product under thermodynamic conditions and which would be the major product under kinetic conditions. HBr (1 eq) //L\e/l§§/’§§/’§§ Br Br . 3' Khalil, _ 3. Vocabulary: (14 pts) Fill in the blanks with the approprlate vocabulary word. If two bold words are given circle the correct one. A) A —NH2 / -OCH3 / -Cl is a mild activator by induction. B) An ortho/para director is always @I never and activating group. C) True KFalseh Diels Alder reaction works by a stepwise mechanism with intermediate ions. D) True ight can close a triene to a cyclohexadiene and does so in a disrotory manner. E) A —CF3 l -N02 -C / -COR is the most deactivating, all these functional groups are directors F) Conjugated systems are @/ less stable than unconjugated systems and are also or / less reactive than unconjugated system. G) Aromatic systems must be CYCIIC , COfildfiH , glaw and have 51 a t 2 pi electrons. H) Natural rubber is a polymer of isoprene that is elastic due to 1) True Benzene undergoes reactions similar to other alkenes. 4. Mechanism: (12 pts.). Show detailed reaction mechanisms for the following reaction. Include all relevant resonance structures and the structure of the expected products. HN03, H2504» C) ‘\ PKG“) // Q) ” ' - G: a o 4- N Pkg—“6:96? M/o N\06 €— Hfl n H’Hsoq HSOq Q) C: 6) (D ] £6.) Q) N \ ” / \ f\\0 e— )l\ L: éa l) ‘ 669 ‘ .~ 0 \ O A ‘/\H 0234/ H 0&4 '4 9“ \l/ \ \ ’ Q) a © 0 6M HQ 7- 9— 0) H5011 5 . Synthesis: (14 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. N H 0 I l P H l @ View @ lysof /l\ O 0% \ ZVaCH7\ ‘ _ \ \ “25"”! N01 © 6. Identification: (6 pts) Label each compound as aromatic, non-aromatic, or anti W 6 Mai he") flL__ Mfié anbaromqbi. Q 0 N/ Micfl_ 7. Nomenclature: (8pts.) Provide the systematic names or structure of each of the following compounds include E/Z Where relevant. o V . “. ‘i’k l-Z- eh l-b-ox he innai 2 +Q’Wl’ A>1fittHse~I MY 0? P4?” 0 MaSOrew 3- ckioro— 5 - {Sopropyl phenol q a B) °' . ’ .l-benzenol . Micro-5 'SOP'W‘I' Cl 3 z | OH évZWoro- 5' (l'meh‘lleh‘qnpunai 0 Br 3-b¢omo-\-P\nenq\-\-Pcni'¢w¢me C) M91. D) m-butyl-nitrobenzene E \ W 8. Reactivity: (4 pts) Circle the carbon(s) on each molecule that is/are most likely to be substituted in an electrophilic aromatic substitution. 1 Pt each fiCOOH S OCH3 0CH3 §> 9. Spectroscopy: (20 pts.) The unknown compound A (C16H2402) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. at“ M 2“! 2H IR: 3036, 2955, 1690, 1210, 810, and fingerprint cm=1. o h (101M249, - : 2 ~5 j 2 ¥ o\ @P ——7 G: 9h {L / ‘ zP’r . 3 *5 ‘ - cm. *4 0'65" P I © 0 ,c‘ 10? CH5 @ 2%,. 932a»; sash} ICH3 *5 no ’ Cx ‘ “’3 3" look {3” Nov—18‘! ...
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This note was uploaded on 02/21/2012 for the course CHE 118B 118b taught by Professor Many during the Spring '12 term at UC Davis.

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118BSpr10MT2Key Livens - 1. Reactions: (32 pts). Draw the...

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