exam_key3a - Name: First Last E QQ 1m 2; CWlD: Seat Number:...

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Unformatted text preview: Name: First Last E QQ 1m 2; CWlD: Seat Number: Chemistry 3053 Exam 3, 100 points Thursday, October 27, 2011 GENERAL INSTRUCTIONS: Write name, CWID, and seat number on this page ) ) Check for 10 pages (including this one and the last page with the periodic table). ) Sign the attendance sheet when you turn in your exam. ) 1 2 3 4 Keep your exam flat on the desk in front of you. You may only have a writing utensil and your model kits. EVERYTHING ELSE MUST BE PUT AWAY. No cell phones No calculators No electronic devices of any kind. Show Your Work. Be Specific With Your Answers and Write Legibly (if we can't read it, we can’t grade it) GOOD LUCK When your exam is returned, your score will be on the last page. 1 Page Point Total 1) Mark the letter answer leginy (A, B, C, or D) for each question in the blank to the left. (14 points) 3 1) Identify which anion would be the least nucleophilic in aprotio solvents. A) F“ B) I” C) B!“ D) Cl' 8 2) Identify the most stable alkene. A) SN‘l B) 8N2 C) 8N1 and 8N2 D) E2 82 4) Identify the compound that would be the strongest nucleophile. A) H20 B) 'OH C) CH3002‘ D) CH30H E 5) identify the most stable carbocation. A 6) Identify which alkyl halide would react the slowest via an 8N2 mechanism. D) A) B) F C) ©/I )V M Br MCI 2 7) Identify the conditions that most favor an 8N1 mechanism. A) 'CN in DMSO B) MeOH at 25 °C C) EtO' in EtOH D) F" in acetone 2 Page Point Total 2) i) Designate the following compounds as either E or Z. (4 points) \ l I A B) ) EH0 H308 Et H30 F H300 NH2 _Z—_E_* ii) Designate the following compound as either 8 or R. (2 points) 3) Show how you would use a nucleophilic substitution on an alkyl halide to synthesize the following compounds. You may use any other reagents necessary (fill in the boxes). (12 points) ‘ A) ’2. S ’2. La M + f 0' ——> YOM B) O 0 'LG‘ N + \/\L O— ———>— \JLON C) 3 Page PointTotél k E 2 4) Predict the maior product for the following elimination reactions. (8 points) A) major product H30 CH3 t-BuO- Hal __c H H3O CH3 t- H30 Br CH3 M50' x MeOH 5) If going by an 8N2 mechanism, which reaction in each pair would take place faster (indicate by circling). (8 points) A) /\/ + “4480’ —-~——’- + BI” Nl + MGOH flaw—b Nome + HI 4 Page Point Total I 6) An example of a competition experiment is one where there are two potentially reactive sites on a substrate and the two reactive sites compete for a single reagent. A) For the following substrate and reagent, predict the major product of the following experiment. (4 points) major product H o B) BRIEFLY explain the reasoning behind your choice. (5 points) l -——» ' W3 0% Uqloncit. l ‘93:? gmafi gul 7) Briefly explain the following statement: (4 points) The following reaction: ——“‘—> M Br + 'OTs + N34” t ' \l€ buci’ Obi“ DWO 00m SBQVQE/ Pbg'h cope WW? 3 Calb ..,, er B ' (D niSr‘r 358erde OD met,“ up D‘MS r 8'0 mac/)6 «COSVQ/ proceeds 100 times faster in DMSO than in EtOH. 5 Page Point Toté’ll 2 8) Give the expected major product and the mechanism by which it is formed (SN‘I, 8N2, E1 or E2) for the following reactions. (15 points) 5 PD‘FH’S 2. P’QIu’fi'S Product Mechanism A) MeO' /\Ci/\ MSOHI 50 CC . a B) Br 3: ? l' _ /\/\(\ ——>DMSO W 2.. C) +1 )(OW’ El 9) State whether or not the following nucleophilic substitution reactions will occur. (Yes or No). (6 points) A) Yes or No /\/CQ OCHS QCH3 \ —'———n— 7 —CN DMSO M + B) B OTf ~———+'Br J + ~OTf /\/’\ DMSO M S 6 Page Point Total g 10) Given the sawhorse structures for the 4 possible stereoisomers of the following compound. 9H CH QH OH OH OH OH OH i ii iii iv a) Identify if there are any meso compounds. (2 points) or No (Circle the correct answer) 1 + l \ we at b) Are there enantiomers present? if so, designate any pairs of enantiomers. (4 points) 00 l'h Ca and . =enamiomers - and - zenanfiomers o) Are there diastereomers present? if so, designate any pairs of diastereomers. (4 points) it! i d) Do meso compounds rotate plane~poiarized light? (2 points) Yes or (Circle the correct answer) 7 Page Point Totél 11) Fill in an appropriate starting material for the following reactions. (6 points) A) (starting material) "substrate" EtO' —> \ /\[/\ EtOH, 65 00 M Br 5,. LG: B) (starting material) "substrate" get 0 \Lo '5 /\/ ' O ——> i EtOH. 25 DC 8 Page Point Total Extra Credit: Organic Halides like CH30I and Cchlg are slowly decomposed in the environment by reaction with H20. It takes over a year for half of the CH30| to convert to CH30H by nucleophilic substitution. 3) Give a plausible explanation as to why this reaction is so slow. (4 points) Scratch Paper Only — Nothing written on this page wi I be graded. i‘nmmum ‘7 warms (Imwflmfiy; ell-magenta Human Amide Nuuhc: 53mm“ Atmnir. - Weight 3 6 7 S 9 10 11 1‘2 r1‘. 2 4 . - «m u mm wlmium mmmu mnmmw mm m" Inwi Tm: T " ?II '22 23 24 15 25 2? B 29 35 mo! um:- _ a w sma- 9m: 54 ‘1 «we c5254 wm H t i "'31" In ’5 ctr i'i‘ 5 WI VHF!!! IU NED-UN 3m? «Emu?! 39 4:) £1 a: 4: 4-1 as 49 4? 43. Hit E “'33.! r W ' A -' ‘ . ' :\ I 71 Si m- _ , IEiIIJII mama Liflllum' .32 .3 a I M 34 Ge As 8e E I n- m alum w ,m V . 49 i so at 52 in Sn Te 1 ‘ mgg‘igg‘m < 13%; V mm: A. an. maul mean Mush-n mn- m'zvknn .Imr me E am: ; i nflfllua' ‘ 32 73 74 75 75 ‘77 79 M g ‘32. E Si 54 55 Ta W Re Ga ir‘ Au 7! i Pb Bl Po At was mum 123:” urn Wm___§m7._ n. 7 1 . m.- mmm- . mm A . 4; . m = . mm; a. 335 “37 109' 13 “3 E 5g Eh H3 Mt Um: LIqu 1 . .. .. V‘ l! , '3'" .nmkfifiimm Tms‘d ion Metals Oak, t Mam Smimmtl'm. Rmhmmélrbkme Rust) Shamans E Liquid; «Emil; .m- Le Var! Iran “an: imam: alrlnmts synltwtic shamans 10 Page Point Total ...
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This note was uploaded on 12/22/2011 for the course CHEM 3053 taught by Professor Laurashirtcliff during the Fall '11 term at Oklahoma State.

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exam_key3a - Name: First Last E QQ 1m 2; CWlD: Seat Number:...

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