Chem 308_Summer 2010_Exam 1h

Chem 308_Summer 2010_Exam 1h - Student Name (PRINT...

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Unformatted text preview: Student Name (PRINT CLEARLY): ‘ - Chemistry 308 H Exam 1 July 20, 2009 Student Signature: Section Number (H1 before lecture, H2 after lecture): ' SEAT NUMBER: Instructions PRINT YOUR NAME AND SECTION NUMBER AT THE TOP OF EVERY PAGE. ' ‘ You will get no score‘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 of the information requested at the top of this sheet. 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 any_gf_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. Exam Form Number: 1 SECTION (H1 or H2) PRINT NAME ‘ 1. Draw a resonance structure of the DNA base thymine, below, that best illustrates its aromatic character (2 points)? 2. Draw a line~bond structure Showing all covalent bonds except carbon—hydrogen bonds and indicating gl_l formal charges for 4-nitrophenol'(3 points). ' 3. Draw thegmajor organic product of the synthetic transformation below (3 points). 1. HNO3, H2804 2. 13:2, Fe .__.——————-———————--————-—-> 3. H2, Pd—C Total points this page (max 8) 2 PRINT NAME SECTION (H1 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). - v OH OQN ’ OQN 5. Use appropriate shading of the p-orbital diagram below to generate a diagram showing the HOMO— LUMO (frontier orbital) interactions in the Diels-Alder reaction of the compounds shown (2 points). ' CN NC 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). ' ' o O a # Total points this page (max 8) : PRINT NAME SECTION (1-11 or H2) ‘ , 7. Give the major organic product expected for the reaction shown below (3 points). //’. rnch,rnscrb300°c- .___._..__————-—-—————-—-> ? \ N 8. Write the IUPAC name for the compound shown below (2 points). OH O M. 9. Write a detailed mechanismforthe reaction shown below. Use curved arrows to indicate all electron movements, and indicate all formal charges (3 points). ' OCH3 ' - OCH3 B;——Br , 3’ ..__...———-—-———-—————-————> g I Total points this page (max 8) = PRINT NAME V SECTION (H1 or H2) 10. Draw the structures of all organic products expected from the reaction shown below,~ ignoring stereochemistry (2 points). NBS, hv —-4——> ? 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 f or incomplete answers, only if intermediate products are indicated (3 points). ' OH . ? V \/\OH ___________________________> Total points this page (max 8) : PRINT NAME r ' . SECTION (H1 or H2) 13. Draw the structure of the compound that gave the IR _spect_rum (top), the 13C-NMR spectrum (middle) and the 1H—NMR spectrum (bottom) shown on the next page (3 points). ' STRUCTURE: 14. Number the compounds show below in order of their relative rates of solvolysis in methanol (1 : fastest, 4 = slowest) (2 points) ' /\/\Br Ma Br/\/ Br 15. 'Draw the structure of the major organic product of the dehydration reaction shown below (3 points). _ O l + .J\ THZ‘O‘ 9 _——.———————-——--——-)> N V . H . . Total points this page (max 8) = [00 TR HNSHKTTHNCE! 2' 01 a 4 D00 11 3000 EON {MK 200 10 180 160 “\'\-'Nm@ 2H 20W 140 3H HRVENUNBEN >1! .[1$'» 120 Jim uAMXS 100 80 \H 80 . 1000 40 20 5H0 -A an aldehyde and an alkene PRINT NAME - SECTION (H1 or H2) [00 HMSMITIMEIE' on V a “00 V r 3000 200D HM 1000 no IRVLNUHIIII «l i 16. Which two functional groups are indicated by the IR spectrum shown above. Circle the answer (2 points). ‘ ' B an alcohol and a ketone C an alcohol and an alkene D a ketone and a benzene ring E alkene and a benzene ring 17. Which compoUnd is the major product of the reaction shown? Circle your answer (Zipoints). A .._..._...._.> * ‘2 W + NC cN ' CN ficN v CN .“\\CN ' . ' ON ON i ""’CN y CN ""”CN "II/’CN A B C ‘ D E . Total points this page (max 4) : PRINT NAME SECTION (H1 or H2) 18. Which chemical argument(s) best explain(s) the o,p-directing effects of a methoxy (—OCHB) substituentlon benzene in electrophilic aromatic substitution reactions? Circle your answer (2 points). A‘ inductive effects only B hyperconjugation only C inductive and resonance effects ‘ D resonance effects only E hyperconjugation and inductive effects 19. Which compound or ion is aromatic? Circle your answer (2 points) H H \@/ H\N/\le?/H N \:_J \ / A B C D E '20. Which one compound is the thermodynamic product expected from the addition reaction shown below? Circle your answer-(2 points). ' HBr ~ I \x ‘ l . . i ? /\/l\ I \/l\/ Br B Br / ' \ _ I Br / Br B C I D E A Total points this page (max 6) = ...
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This note was uploaded on 01/12/2012 for the course CHEM 2347621 taught by Professor Mr.boikes during the Summer '09 term at Rutgers.

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Chem 308_Summer 2010_Exam 1h - Student Name (PRINT...

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