Chem 308C_Summer 2011_Exam III Key

Chem 308C_Summer 2011_Exam III Key - Chemistry 308 C1/C2...

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Unformatted text preview: Chemistry 308 C1/C2 Exam 3 July 13, 2011 Student Name (PRINT CLEARLY): é; Student Signature: SEAT NUMBER: Instructions Please fill out ALL of the information requested at the top of this sheet. Use a pen, not a pencil. This exam consists of 8 multiple—choice questions and 12 questions requiring written responses. To answer a multiple—choice question, circle the letter corresponding to your ansWer. Questions requiring a written response should be answered clearly and legibly and only in the space provided. Please answer all questions within this exam booklet only. At the end of the exam, you must hand in this complete exam booklet. Do not separate any of the sheets in this booklet or remove the staple. Do not hand answers in on extra sheets. The length of the exam, including time allowed to fill in all responses, is 70 min. Exam Form Number. 1 \ . Which one of the compounds shown could be used as the initial reactant in this synthesis (2 points)? 0 1. one equivalent CH3MgBr, THF 7 MW.» 2. dilute HCl, H20 w ~h ' 0 V ' 0 /\/\Br MNHZ NH /\/C” ' /\/u\0. A B . [C Q E f“ r organic product expected from the reaction shown below (2 points)? A . Which is the majo OH -' O HZNNHZ, KOH, H20, A W ‘7 O' OH OH E I l H CU A B C O O OH Total points this page (max 4) = z. . Give the reagents and conditions to show how you'would use an enamine to perform the synthetic transformation below (3 points). ‘ gr Sikh“ £§> ) l€\d\\U-\ 0 (2“ OxYY‘M‘Cl . O O M o' /“\ _‘ f W034ng adj-\Ex ganic compounds needed to synthesize the compound shown below in Draw the structures of the two or (3 points). good yield using a crossed Claisen condensation reaction it. ® . . Q \\ 0 Qt \\ o o l/ \\ + WW:- V (349 ' 9 1. NaOEt, EtOH OEt . 2. Dilute aqueous acid (L a O O‘ , .r’“ NR. > - \ (/‘l + Ero)\0@\ \. \/ Draw the structure of the major organic product expected from the reaction below (3 points). ’5 . c 1 ' NaOH, 0 O O rififiigon, A W 7 \ /\ 3 Total points this page (max 9) 2-. Q . Write the IUPAC name of the compound below (2 points). :l' . Draw the three most important resonance structures of the intermediate in the reaction below (2 points). Cl OH \N ‘ (a l \N ‘ (5L1 \ ’ ' o A >/\ UL 0-“ 9H \l\ é—‘D [I \\ > ‘\ l 29 J N H . \ ~ to / ED Cg . ‘Write a detailed reaction mechanism for the transformation below. Use curved arrows to describe all ll formal charges clearly (3 points). electron movements and indicate a \A ' a,- ‘, . \%g\v\ % H2804, H20 V O” l ' ~ l /K H ' ® . CM is . M a ,b/H V'l H Total points this page (max 7) = W C\ . Which is the major organic product expected from the reaction sequence below (2 points)? - 1. NaOEt, EtOH ' __._..___.—_——-———-> '2 2. H20, HCI o M03 O O O O 0 . . o , woe: _ OEt B c @ E W . Which amine CANNOT be synthesized by a reductive amidation (2' points)? HN/x ‘ / ' . . Ly © s A B D t E s\ . Which compound will decompose in base by a retro—aldol mechanism (2 points)? 0 OH O O 0 OH M OEt H <9 B c ‘ o \ 0 M E D E Total points this page (max 6) : W l7, . Give the reagents and conditions necessary to perform the synthetic transformation below. More than one step is required (3 points). i;<3Q&1)Q (ng‘t‘xlib O . . \ . I)“ Lfigcafilwgfa’} 2 :l—prk‘i‘nai /\\/\ i . N /\ OH . H g i 1,; mm; ) ml: 4: mo \3 . Draw the structure of the organic compound that would give the product shown belOw in an aldol addition reaction (3 points). catalytic NaOH, 0 . H O, CH OH \._).\\\1\ ,___:___3____.... H thetic transformation shown below. Use curved arrows to show \47 . .‘ Write a detailed mechanism for the syn ints). all electron movements, and indicate all formal charges clearly (3 po '6 0 Excess CH3MgBr, THF 4 O as ~ Bf' 3' /‘ Total points this page (max 9) :: \Sl . Rank the compounds shown below according to their rates of reaction with sodium methoxide in methanol (> means faster reaction than) (2 points). Cl 0 fl \N \N Cl ‘\N‘ Cl K L p M N ®N>M>K>L ' BM>N>K>L C-K>L>N>M DN>Mi>L>K EK>N>M>L FK>L>M>N . What is the major organic product expected from the sequence of reactions shown below (2 points)? ' No2 1. 13:2,133 2. H2, Pd~C I? O 3. NaNOZ,HC1, H20, 0 °c 4.C,uC1 ‘ , . » CI NH NHZ NH2 Br - 2 i ' Cl Br ' Cl N02 CI ‘ E :L m 8’ ' Br NO2 A ‘ B (C) D E r base strengths (> means stronger base than) (2 points). l} . Rank the ions shown below according to thei ('3 (-3 9 O ' O O N /\O/l\ MOA A09 \V L . K M N AN>K>L>M BK>L>N>M CM>K>L>N @N>K>M>L 'EK>N>M>L FN>L>K>M Total points this page (max 6) = \% . Draw the struCture of the rnaj or organic product in the reaction sequence below (3 points). 1. NaZCr207, H2804 ‘ ' M ? - OH 2. Excess CHgLi, THF 3. Dilute aqueous acid \q . Give the reagents and reaction conditions needed to perform the synthesis below. More than one reaction is required (3 points). 0 i ER}? 0 1C) . Write a detailed mechanism for the reaction shown below. Use curved arrows to describe all electron - movements, and indicate all formal charges clearly (3 points). 0 (i O O . O NaOEt, EtOH /u\ + t OEt OEt . O E Total points this page (max 9) : ...
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Chem 308C_Summer 2011_Exam III Key - Chemistry 308 C1/C2...

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