Exam_I_Key_Summer_2009_h

Exam_I_Key_Summer_2009_h - Chemistry 308 Exam 1 KEY Section...

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Unformatted text preview: Chemistry 308 Exam 1 July 20, 2009 KEY Section Number (H1 before lecture, H2 after lecture): Student Name (PRINT CLEARLY): ' Student Signature: SEAT NUMBER: Instructions PRINT YOUR NAME AND SECTION NUMBER AT THE TOP OF EVERY PAGE. ' ‘ You will get noscore for the pages missing your name. You Will not get a copy of your exam if the pages are missing your section number. ' Please fill out _A_L_L_ of the information requested at the top of this sheet. A This exam consists of 5 multiple—Choice questions and 15 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 a_ny_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 75 min. I Exam Form Number: 1 PRINT NAME SECTION (H1 or 1-12) V 1. Draw a resonance structu character (2 points)? 2. Draw a 1ine~bond structure sh re of the DNA base thymine, below, that best illustrates its aromatic _ - Cf H36 /\\f§,+\ “‘19:?“ \\\ ‘ - ‘ ‘n r, \fi /\ .9 ““3ng EB: O WXS ,\ . owing all covalent bonds except carbon~hydrogen bonds and indicating all formal charges for 4-nitrophenol (3 points). 3. Draw the major organic product of the synthetic transfo rmation below (3 points). Nth. 1 HNO3,HZSO4 ' \ 2. Brz, Fe 9 \\/’\~\ W . Total points this page (max 8) : _ PRINT NAME SECTION (1—11 or H2),,________,_ 4. Give the reagents necessary to perform the synthetic transformation shown below. Number the reagents for separate reactions, as usual. Partial credit will be given for incomplete answers, only if intermediate products are indicated (3 points). l. (2%,) $3 of” {9%)93 _ OH 02517: j ? ’1. (hf 3 TR? OZN ' Q . 3 )‘\. - ~ l \ diagram below to generate a diagram showing the HOMO— 5. Use appropriate shading of the p-orbital the Diels—Alder reaction of the compounds shown'(2 points). LUMO (frontier orbital) interactions in 6. Number the compOunds shown below in order of their rates of reaction with bromine and iron filings (BIZ, Fe). (Fastest: 1, slowest: 4) (3 points). an on '1'» ‘i’3 Total points this page (max 8) z PRINT NAME V SECTION (H1 or H2) 7. Give the major organic product expected for the reaction shown below (3 points). NO / I~H\T03, H2804, 300 °c //\/ L n M ‘2 \ 3 \N N YR3:3: 1'30 QOVXA ‘4 V M I “~leer 3 9. Write a detailed mechanism for the reaction shown below. Use curved arrows to indicate all electron movements, and indicate all formal charges (3 points). OCH3 oer—13 V . , (.3 B " :jflBrwBr . V FV Total points this page (max 8) = _ SECTION (1-11 or 1-12) PRINT NAME '10. Draw the structures of all organic products expected from the reaction shown below, ignoring .' stereochemistry (2 points). . ' (7; ( NBS,hv / .‘ /\ \ 9t» owls. 11. Draw all important resonance structures ‘for the intermediate in the reaction shown below. Indicate all formal charges clearly (3 pOints). 12. Give the reagents and steps needed for the following synthetic transformation. Number the reagents for each reaction separately, as usual. Partial credit will be given for incomplete answers, only if intermediate products are indicated (3 points). OH - . Area, smile. V\OH , ~ Total points this page (max 8) = PRINT NAME . ‘ SECTION (H1 or H2) - 13 Draw the structure of the compound that gave the IR Spectrum (top), the 13C— NMR spectrum (middle) and the 1H— NMR spectrum (bottom) shown on the next page (3 points). STRUCTURE: ‘ ' . Q3- 10%?) . . 31/. ,l @ é (\Hmé Q 2 l //’ \Q’K can)“ 14. Number the compounds show below in order of their relative'rates of solvolysis 1n methanol (1 = fastest 4— - slowest) (2 points) \. /k/\B 3M B/Q\ *2 , \ I 3 i I OkaALQeY 15. Draw the structure of the major organic product of the dehydration “reacgon shown below (3 points). (7 / Total points this page (max 8) = {00 TI ENSM TTHNC E! 1U a: a 4500 3000 20011 15110 . 1000 am IFWENUMEN HI ‘ZC‘N {MK 2. Skywxs 200 180 160' 140 120 100 80 60 40 20 0 "‘4’ng , y' . .r 6H , ’SH 0 1H \H 11 10' 9 8" 7 e s 4 3 2 1 o PRINT NAME ' 5 ' ; SECTION (H1 or H2) (00 mnsmrmczm S "00 3000 200“ [IN 1000 “0 . URVENUHIEII «I - 16. Which two functional groups are indicated by the IR spectrum shown above. Circle the answer (2 points). ' ' '.A' an aldehyde and an alkene @n alcohol and a ‘ketone . C an alcohol and an alkene D a ketone and a benzene ring B an alkene and a benzene ring I V 17. Which compound is the major product of the reaction shown? Circle your answer (2 points). Total points this page (max 4) = PRINT NAME SECTION (H1 or H2) 18. Which chemical argument(s) best explain(s) the o,p—direcu'ng effects of a methoxy (~OCH3) substituent on benzene in electrophilic aromatic substitution reactions? Circle your answer (2 points). A inductive effects only B thyperconjugation only C inductive and resonance effects ©resonance effects only E hyperconjugationand inductiveeffects 19. Which compound or ion is aromatic? Circle your answer (2 points) H H G) H / \ I/NW H\N/\C;)/H \N/ __ NH HNVNH \__‘_/ \; /; 20. Which one compound is the thermodynamic product expected from the addition reaction shown ' below? Circle your answer (2 points). VHBr '\ , , ———————-———-————————-——-——————-——-—> ‘2' W/K A/k \/I\/ \/‘\/ Br Br Br / , \ ’ Br _ / Br 94 Total points'this page (max 6) = ...
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