Chem 308_Summer 2010_Final Exam Key

Chem 308_Summer 2010_Final Exam Key - Final Exam August 18,...

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Unformatted text preview: Final Exam August 18, 2010 Chemistry 308 Student Name (PRINT CLEARLY): K Eh! Student Signature: Sectidn Number (H3 before lecture, H4 after lecture): SEAT NUMBER: Instructions Please fill out ALL of the information requested at the top of this sheet. This exam consists of 12 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, is90 min. Exam Form Number: 1 be used as the initial reactant in this synthesis (2 points)? 1. Which one of the compounds shown could O O 1. NaOEt, EtOH, A 7 WM 2. H20, HCl to neutralize E10 ’ N . 0 Et OEt _ H O . A B C ' EtO » H i H H - o O , G) E 2. Which is the major organic product expected from the condensation reaction shown below (2 points)? H _ O > N . /u\ + ‘ ‘ catalytlc H2804 (-HZO) . V 7 M ? C: 60% a 0% Q C Total points this page (max 6) = 4. Which sequence of reagents Will produce the synthetic transformation shown (2 points)? , N02 @1.CH3CH2COC1,A1C13; 2. HNO3,HZSO4; 3. HZNNH2,KOH,HZO,A B 1. HN03,sto4-, 2. CHBCHZCOCLAICI3; 3. H2,Pd—C C 1. CH3CH2CH2C1, A1C13; 2. HNO3,H2804; 3. NaBH4,CH3OH D 1. CH3CH2COC1, A1C13; 2. HNO3,HZSO4; 3. NaBH4,CH3Ol-I E H2, 5. Which is the correct description of the an molecular orbitals in benzene (2 points)? A 2 bonding; 2 nonbonding; 2 antlbonding B 1 bonding; 4nonbonding; 1 antibonding ©3 bonding; O nonbonding; 3 antibonding D 4 bonding; O nonbonding; 2 antibonding E 2 bonding; O nonbonding; 4 antibonding 6. Which compound is the strongest acid (2 points)? 0 r O O O . O . /U\N / io/ ' /u\ ' H . A I B C D Q Total points this page (max 6) = 7. Which sequence of reagents Will produce the synthetic transformation shown in good yield, assuming that ortho— and para-substituted products can be separated (2 points)? OH NO2 A. 1. HNO3, H2304; 2. C12; Fe; 3. KOH,H20 B 1. KOH, H20; 2. HNO3, H2804 c 1. (212,142.23. KOH,HZO; 3. HNO3,H2804 D 1. HNO3, H2804; 2. KOH, H20 @1. (112.1%; 2. HNO3,HZSO4; 3. KOH,HZO OCH3 8. Which compound is most reactive with sodium methoxide in methanol (2 points)? ‘ Cl F C! ‘ N02 ' i i .ocH3 f ,No2 f Br i , it * ’ o D E 9. Which compound is most reactive with HBr (2 points)? Usssv A - B Total points this page (max 6) = 10. Which one of the compounds shown below gave the IR and NMR spectra on the next page (2 points)? 0 OH o B _ A C O )KQ‘K O HO H W @ ' E 11. Which compound will break dowfi by a retro~a1dol reaction in base (2 points)? 0 O OH O * O ' O HO O OH M H _ OEt B c D . ® 12. Which reagent(s) Will give the best results for the reaction shown below (2 points)? 0 \JKH B H2, Lindlar’ 8 catalyst A O 9 1. AlBuiZH, —78 °c; 2. HC1,H20 c 1. LiA1H4,THF; 2. HC1,HZO WM D PCC, (31412012 E 1. LiAl(OBut)3H,.THF; 2. HC1,H20 Total points this page (max 6) = \D‘D TX mum: \‘TMCEI 1U 01 a rr‘.rr"fv cr1r—w’41rr-1— ~r r 3090 tom: 15 D0 1090 sun )Lcn'enunamm r T‘ 1 I r ’1 T 1 ' r T 7 ’r 1 '1 y 200 180 160 140 120 V 100 80 60 .40 20 0 L l L -JL .J ‘I 1"" r‘rf‘ r '7'" ‘1‘ 1' ’r" ‘ --r— 12 10 8 ' 4 Z O —z 13. Draw the structures of two organic compounds that could be heated together to make the compound , shown below. Indicate stereochemistry clearly (3 points)‘: A . m A l: ' Jr— \"\ ‘ \ {hmmfimwa (00$ 14. Draw the structure of methyl 3—oxobutanoate (3 points)": o O /l o/ -"\ gar wwwss ‘S Mafirwm 15. Write a detailed mechanism for the synthetic transformation shown below. Use appropriate curved arrows to show all electron. movements and indicate all formal Charges clearly. You may simply indicate proton transfer reactions as + H+, or - H+, as appropriate (3 points)‘: 0 )K/Br o BIZ, H20, CH3C02H Total points this page (max 9) = 16. Give the reagents and conditions needed for the synthetic transformation below. Use numbers to indicate separate reaction conditions (3 points). ' N02 \ g ) Cl 7""1.I\A\$)Q§\*C of “inflik . ‘ ‘3; Meet) Hot) His) 0% Ar. (not Cl \ 17. Draw an energy profile for the reaction shown below, using the axes provided (3 points)£ O O O 9 9 Cl ' o Enthalpic Energy, H0 Progress of Reaction 18. Write a detailed mechanism for the synthetic transformation shown below. Use appropriate curved arrows to show all electron movements and indicate all formal charges clearly (3 points). 0 OH jg catalytic NaCH, EtOH M . H ' ’ r H ,i j - ,QC'S’C’ H H m A nbaif (9:6; 0 /-// <06 Total points this page (max 9) = 19. Draw the most important resonance form of the electrophile in the reaction below (3 points). 0 . to . 1. /U\CI , AICI3 2. HC1,HZO Structure of electrophile: C Q 20. Remembering that enamines act as nucleophiles, draw the structure of the product obtained from the ketone below, when it is subjected to the sequence of reactions shown (3 points). 0 \\ /\ O 1- Z 5 , catalytic HCl, A (—HZO) ‘ N _ H ? \ \ O V 2' i0! . 3. dilute H2804, H20 21. Write a detailed mechanism for the reaction below. Use curved arrows to Show all electron movements, and indicate all formal charges Clearly (3 points). F 9 " OH NO2 NO2 Total points this page (max 9) = ’ 22. Draw all of the most important resonance forms of the intermediate in the reaction below (3 points). Brz " 23. (a) Draw a p—orbital diagram that describes the frontier orbital in the reaction below. Use the template provided (2 points) .~ ’ \ A ' / p-orbital diagram: l . . / (b) Is this reaction conrotatory or disrotatory (1 point)? A“ ((9:93‘ 0 F 5 24. Give the reagents and conditions needed for the synthetic transformation below. Use numbers to V indicate separate reaction conditions (3 points). 0‘3 6t 0 O \ EtoJKJKWNthfi-mgx SE (was JvBr mmmmmoia . 0H0» Cab . O ' ) H7?) A _ /‘1 la i, 9 3: Q _\::{3 ’L, \KTG. <~o E \//-'~o /-\..> {3W , 690 Total points this page (max 9) = ...
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Chem 308_Summer 2010_Final Exam Key - Final Exam August 18,...

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