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Chem 308_Summer 2010_Exam 3v (1)

Chem 308_Summer 2010_Exam 3v (1) - Chemistry 308 V1/V2 Exam...

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Unformatted text preview: Chemistry 308 V1/V2 Exam 3 , July 14, 2009 Student Name (PRINT CLEARLY): Student Signature: Section Number (V1 before lecture, V2 after lecture): ' SEAT NUMBER: Instructions Please fill out ALL of the information requested at the top of this sheet. Use a pen, not a pencil. ' 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 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 70 min. Exam Form Number: 1 1. What type of compound is produced when an acyl chloride is reacted with an alcohol (2 points)? A an ester B a mixed anhydride C an amide D anialdehyde E a nitrile 2. If the reaction shown below is allowed to reach equilibrium, which other 18O-labeled compounds will be present in the mixture in addition to the one written in the reaction (2 points)? ”fl _ ‘ ' catalytic HCI lafi —C + H20 V—5 + CH O H HsC \OCHs H3C/C\OH 3 . o A and 0 H3180 H H3O” \WOCHB B CH31BOH only 0 C H and H2180 Hsc" \180H 0 D ICI! only H30 \1BOCH3 E H2180 only Total points this page (max 4) = 3. What is the major organic product of the following sequence of reactions (2 points)? otcrlocond 4. Give the major organic product of the reaction sequence shown below (2 points). 0 0 1. soc12, pyridine, heat AOH 2. benzene, AlCl3 3. H20 0 CD 1. [CH3—Cu~CH3]Li, ~78 °c 2. CH3—I, ~78 °C‘ W - OH OH 0’ o o l.- "A ‘B C D- 5. Which compound is most reactive towards nucleophiles (2 points)? ? 'o OCHs _ o OCH3 OCH3 ; /Tl\ /U\f\102)\ OCHB OCH3 OCHS A E Total points this page (max 6) = 6. Draw the structure of phenyl 2—methy1butanoate (2 points). 7. Write the correct IUPAC name of the compound shown below (2 points). W N \/ ~ ' 8. In the space provided below, draw the structure of the organic compound that corresponds to the IR and 1H- and 13C~NMR spectra on the next page. Note: Any structures drawn on the next page will be ' ignored for grading (3 points). ANSWER: Total points this page_(max 7) : [OD rsansmmmalal 8 41100 3000 2000 I 15m 1000 500 HRVENUHHER! wl ‘3c~NmR 200 180 160 I40 120 100' 80 80 40 _20 0 ~ ‘H—Nma ' 2H 3H 3H 2H 10 9 8 7 6 5 4 3 2 1 0 9. Draw the structure of the major organic product expected from the reaction sequence shown (3 points). H t N 1. i 7 (—H20) 2. CH3Br 3. dil, HCI, H20 10. Draw the structure of the organic compound that Would give the product shown below in an aldol condensation reaction (3 points). catalytic NaOH, EtOH, heat 11. Number the compounds shown below in order of the carbonyl stretch (Cr-O str) frequencies in their IR spectra (1 : highest frequency, 4 2 lowest frequency) (3 points). ' ' o - ' ' o o O o NHCHS A /“\ k /H\ ‘ OCH3 o NHCH3 Total points this page (max 9) = 12. Give the reagents and conditions necessary to perform the synthetic transformation below (3 points). 0 OH \JKO/ ‘ 13. Draw the structures of the two organic compounds that, when reacted together, would give the product shown below in a Robinson annulation reaction (a Michael addition followed by an intramolecular aldol condensation) (3 points).' _ cat. NaOEt, EtOH, heat ? -———---—---—-—-------—--—> 14. Draw thethree most important resonance forms of acetamide (CH3CONH2) (3 points). Total points this page (max 9) : 15. Estimate the equilibrium Constant, Keq, of the reaction shown below (2 points). L +er «=- 2L7? ANSWER: Estimated Keq :: 16. Give the reagent(s) and conditions needed for the synthetic transformation shown below. Partial credit for incomplete answers will be given only if intermediate products are shown (3 points). $ _?______.___._, 55 17. Briefly, explain why base—promoted hydrolysis of an ester is more complete than acid-catalyzed hydrolysis of an ester (2 points). Total points this page (max 7) : 18. Draw the structure of the major organic product in the reaction below (2 points). 0 . CH3NH2, H20, CHQOH _—————-————--—-————-—->— ? 19. Give a detailed mechanism for the ester hydrolysis reaction shown below. You must-show every step in the reaction. Use curve arrows to indicate all electron movements, and indicate all formal charges correctly (3 points). 0 O e /[l\ ‘ OH . . + HOCH /”\O / + W— 06 _ , 3 20. The folloWing synthesis requires the use of protecting group chemistry. Give the reagents and reaction conditions needed to perform this multistep synthesis. NUmber the reactions and show intermediate ~ products for partial credit (3 points). 0 - O O I CH3 . M / M, “Sc 0 H30 , OH Total points this page (max 8) = ...
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