Chem 308_Summer 2010_Exam 2v

Chem 308_Summer 2010_Exam 2v - Chemistry 308 V1/V2 Exam‘z...

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Unformatted text preview: Chemistry 308 V1/V2 Exam‘z' ' June 25, 2009 Student Name (PRINT CLEARLY): Student Signaturei 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. Draw the structure of a compound that could be used as the starting material for the synthetic ’ transformation shown below (3 points)? 1. @115 2'. BuLi O 3./\ 2. Draw the structure of 2—chlorofuran in the space below (2 points). 3. Draw the three most important resonance forms of the organic intermediate in the reaction shown below. Indicate all formal charges clearly (3 points). 1/ t : BIZ H ' H r Total points this page (max 8) : 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, if intermediate products are indicated'(3 points). wwwe—w» JV 5. Give the IUPAC name of the Compound drawnbelow (2 points). w 6. Write a detailed mechanism for the reaction‘shown below. Use arrows to represent all electron movements, show all intermediates, and indicate all formal charges clearly (3 points). HO OCH3 dilute aqueous H2804 i CH OH W + 3 Total points this page (max 8) 2: 7. Give the major organic product expected for the reaction sequence shown below (3 points); 1. CH3COC1,A1C13 2. H+,HZO » . 3. CH3NH2,NaBH3CN,CI—I30H . 8. Draw a Haworth projection showing the furanose '(S—atom ring) structure formed by the carbohydrate ‘ below, which is drawn in its open—chain form as a Fischer projection (2 points). CHO H , OH H V OH H OH > CHZOH Bonus point: In what type of biological macromolecule is this structure most commonly found? 9. Give the reagents necessary to perform the synthetic transformation shown below. Note that the use of a protecting group is required. Number the reagents for separate reactions, as usual. Partial credit will be given for incomplete answers, if the intermediate products are indicated (3 points). 0 o oH Br Total points this page (max fig) : Ci 10. Give the reagent(s) necessary for the synthetic transformation shown below (3 points). 11. Number the structures shown below according to the expeCted frequencies of the C:O stretch absorbance peaks in their IR spectra (1 :2 highest frequency, 3 2 lowest) (2 points). , O O p O /U\ ’ AH 12. Give [the major organic product expected from the reaction sequenCe shown below (2 points). 0 1. KCN, H20 I M ? A 2. HCl to neutralize ' Total points this page (max 7) = , 13. Draw the structures of the two organic compounds that react together to give the product shown below in a dehydration reaction (3 points). _ \N/ + H20 14. Draw the structure of the compound that gave a strong peak in its IR spectrum at 1715 cm‘l, and gave the 13C-NMR (top) and 1H~NMR (bottom) spectra shown ON THE NEXT PAGE (3 points). STRUCTURE: 15. Writea detailed mechanism for the following synthetic transformation. Use curved arrows to indicate all electron movements. Indicate all formal charges (3 points). HO OCH3 i NaOCHg, CH3OH ——-———-—-——-———————--——--———-—-——-——> Total points this page (max 9) = NMR spectra of unknown compound from previous page: 09% 16. Which compound is expected to be most reactive with bromine? Circle the answer (2 points). A B‘ C 13’ lg 17. Which compound is expected to be least reactive towards nucleophilic attack? Circle your answer (2 points). N/CH3 \ng HO O O O A 9 M )k "A B c D p E Total points this page (max 4) = 18. Which type of reaction would produce a secondary alcohol? Circle your answer (-2 points). - A reaction of a ketone with a Grignard reagent in diethyl ether, followed by addition of water. B reaction of analdehyde with sodium borohydride in methanol and water. C reaction of a ketone with lithium aluminum hydride in THF, followed by addition of water. - D reaction of an aldehyde with chromic acid in water. ' E reaction of acetophenone with hydrogen gas and palladium on charcoal. 19. What is the major organic product expected from the reaction sequence shown below? Note that D is the 2H hydrogen isotope, deuterium. Circle your answer (2 points). 1. NaBD4,THF __...________..____,.- ? 2. CH3OH,H20 on :OH D: r : ¢O ' on D p on D v D l A i _ B c - D ‘ ' E_ 20. The IR spectrum on the next page shows the presence of two functional groups. Which two groups are indicated? Circle your answer (2 points). A an aldehyde and an alkene B a ketone and a benzene ring C an alcohol and a benzene ring D an alcohol and a ketone B an alkene and a benzene ring Total points this page (max 6) : ‘ QRICRONS 22 2.3.2.4 2.5 2.5 2.7 202.9 3 4 46’ 5 5.5 7 a 0 10 11 12 1a 14 21 23 25 100 l . _ 1 I J :1 I _ ,4? 00 10 'r R A 2’ 5° 0'1 ! T . . 0 K . ,1 0 ‘1’ if” .4.” E 4 1 . - - .4 - 1: . h ' ~ ' ~ I I :2! 460 «00 4200 4000 0000 0000 3400 3200 3000 2000 2500 2400 2200 2000 1000 1500 1400 1200 1000 ‘2 000 500 400 WAVENUMBERS NICOLET ZDSX F’HR ...
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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 2v - Chemistry 308 V1/V2 Exam‘z...

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