Exam4_key4b - Name First Elf/j Last I géCflflj I I CWlD...

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Unformatted text preview: / Name: First Elf/j Last I? géCflflj I I CWlD: Seat Number: Chemistry 3053 Exam 4, 100 points Thursday, November 17, 2011 GENERAL INSTRUCTIONS: 1) Write name, CWlD, and seat number on this page 2) Check for 11 pages (including this one and the last page with the periodic table). 3) Sign the attendance sheet when you turn in your exam. 4) Keep your exam flat on the desk in front of you. \ You may only have a writing utensil. 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 Tot'eil 1) For the following alkene and indicated reagents give the expected product(s) in the boxes provided. Show the stereoisomers that are formed where applicable. (12 points) ??? ——————-——> Product(s) Br a) 0/ ——‘>2 H20 1 BH 2) H202, -OH 1) 03 c) ——> 2) Mezs B d) 0/ H r 2) Mark the letter answer leginy (A, B, C, or D) for each question in the blank to the left. (14 points) I D a) For a hydroboration/oxidation reaction on the starting alkene, identify the major product. A Ho B 0 CH3 ) ) CH3 ) H30 OH H30 Br OH (5 —» U E? ii 2 Page Point Total l g b) For the following acid catalyzed hydration reaction, identify the major product. f H+ A) OH B) HO C) D) Br ——_‘> HO>—< H20 76 7? 7? D c) Identify which conditions would afford the alkyne from the alkene. 1)??? _ 2) 7?? /— M.—> A) B) C) D) 1) Gig 1) H30+ 1) H-Br 1) Bra 2) NaOH (excess) 2) H_Br 2) NaOH (excess) 2) Nam-12 (excess) C d) Identify the conditions that would afford the product from the given alkene. Br AA ??? AA _—) Br A) B) C) D) cr2 H-Br Br2 1) BH3 2) H202/ -OH A e) For the following acid catalyzed dehydration reaction, identify the MAJOR product. /\(\0H Hgso4 heat D) A) B) C) W fir A? er t) For the following 2° carbocation, identify the most stable rearrangement product. 3 CH CH3 A) CH3 B) C) D) + + + CH3 + + GAG-13 “’9 CH2 3? 9) Identify which set of bases is in the appropriate order based upon base strength. A) B) _ ‘OH>‘CHZCH3 > 'NH2 > :5HCH2 ’OH < 'NH2 < :CH=CH2< H20 C) _ D) _ _ 'OH > ‘NH2 > :CH:CH2> H20 -OH < :CECH < -NH2 < :CHZCHS 3 Page Point Total 3) For the following alkyne and indicated reagents give the expected product(s) in the boxes provided. (12 points) ??? /——:'—_# —-————> Product(s) 2.0 equivalents ex 3‘“ Br2 a) : ——> / E W b) r——/: L———>i’ EtzNH MN/ E NH3 2.0 equivalents Cl 4.- Page Point Total 4) Show how the given product could be synthesized from the given starting material. More than one synthetic step is required. (Fill in the boxes) (18 points) A) 5 Page Point Total C) 5) Propose a plausible mechanism that accounts for the formation of the product from the given starting material under the conditions provided. (5 points) + v w *-—-—”> «<7 6 Page Point Total 6) Give the structures of the possible starting materials that would afford the given products under the reaction conditions provided. (12 points) B) Br Brz Bra“ ——-————-) sto4 \ D) 42., [/h/ 1) 5H3 \ \'\k\ H202, -OH 7 Page Point Total 7) Give the major product that would be formed when each of the following alcohols are subjected to acid-catalyzed dehydration. (6 points) A) M ———» M OH B) OH \ —~» (‘l 8) Given the following information, give the structures for unknown compounds A, B, and C. (9 points) t—BuO- A = C8H14 —————) B = CgH14CI2 CHCg 1) KMnO4, —OH, heat 2)H30+ HBr OH 0 W0 CH C = CBH15BI‘ 8 Page Point Total 9) Explain BRIEFLY, why Hydroboration/Oxidation affords the anti—Markovnikov product (mechanisms and structures are your friends) (5 points) 696' ‘Zflg ME‘KCUVN Ar 0t 10) a) Using 1,4-dimethyicyclohexene, demonstrate that addition of HBr is not a stereospecific reaction. Draw the structures of all the stereoisomers formed from addition of HBr to the alkene. (4 points) gage (Log "Ff/Wm 40x 9 Page Point Total b) Using 1 ,4—dimethylcyclohexene, demonstrate that addition of HBr is a regioselective reaction. (3 points) Extra Credit: (6 points) Why is compound X formed in the following reaction, instead of its constitutional isomer Y? (Use mechanism and structural reasoning) HCI 0' l W NOT 0 0 Cl 0 x Y 66.6, @{36 EMCMNQ 41$ 10 Page Point Total Scratch Paper Only — Nothing written on this page will be graded. periodic table of the elements )3 wants “0‘ m1 18 Almlins K} :m ,l (manningng 2 . [Edam — Emma: 7 ' "1am? fl”? — 3_ 1‘ mum. LI Ll _ Symbul L] Atoimc l; m Wa‘ght hmllln‘. 3 11 M) N a 72 {Mi 5 ammom mm mm; mm 19 a: 5! 6:545 (£5 :3; V, yummy 23 Fur ' a . “mum llu‘mu. paw» we: mum-u. 41 112 48 . 4H , . Rh Pd Ag w ‘: rx:1lnlu:n ' m V Eur-Q; mamm- nmmm A J 72 74 75 76 ,78 ' w. v ,1 ll "‘5 r . w: I I . : 1' m , I ‘ . mumqy ‘ re umm 122 (El mar:er 7_ 37 [Q Fr m hurl” “IL-N mum: Liquids Elm-ml: 5y be van nan can: Gaseous s‘mnmls synaheila skmmts Score: 11 Page Point Tot'ail ...
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