MS E3 Spring 04 - CHEM 243(Dr Montague-Smith Organic...

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Unformatted text preview: CHEM 243 (Dr. Montague-Smith) Organic Chemistry II Examination III 30 April, 2004 YOUR NAME _————._._.._—_.—______—..___ (Last, First, MI.) DISCUSSION SECTION #82 _ Initial of last name Instructions - Please fill in your name in the space abdve and on the next page - Please put your discussion section number in the space provided. - Print the initial of your last name in the box above - Sign your name under the Honor Code acknowledgment cattle following page - Failure to sign the Honor Code Acknowledgement will result in the forfeiture of your right to request a regrade ° DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO - Please provide your answers in blue or black pen. Use of erasable media will forfeit your chance to request a regrade. Cross mistakes out completely - Answer uestions in the 3 aces rovided 1. (60 points) For each of the reactions below and on the following two (:2) pages. provide the MAJOR organic reaction product(s). If no reaction occurs, write "NR”. If the reaction is an equilibr-um reaction, assume product formation. Stereochemistry is only important for the carbohyrdate problems. A. NH2 1} HNO 2) CUCI NH2 1) HNO 2) l-l3P02 o O/LNHQ _ OH‘ gxsy Br2 ly<OH 2) t-propyl bromide 3) H30+ NH 1) Na+N3 CI 3) A Problem 1 continues on next page Problem 1 - Continued B. HO O OH OH NaBHg OH OH HO O OH OH EtOH /H+ OH OH O ‘OH (XS)/I2 (XS) ——---—-—'> CH3 0 \A EtO‘(1 equivalent) ————> OEt O 'OH (XS)/A —-—> Problem 1 continues on next page Problem 1 - Continued C. H 0 HO H 1)NaCN H OH 2)H2/ Pt ' H OH 3)HaO+ OH HO O OCH; CH _ NaBH4 OH OH 0 A 1)LDA OMe 2) /\‘/\Br 3) OH‘/A NH HMO2 H3c—N=c=o *flaQL» 3. (30 points) For the transformation below, provide a detailed arrow-pushing mechanism. lf intermediates occur which are stabilized by multiple resonance forms, show all resonance forms. 0 O O H 30"” H 4. (20 points) On the following page is a collection of spectroscopic data corresponding to a, particular molecular structure. Using the data provided, determine the structure for the molecule. Draw your structure in the box provided. Table of IR and NMR information is at the end of the exam Draw your structure in this box ____l 4000 3000 2000 1600 1200 son v (cm") Mass Spec1mm 4o 80 120 160 200 240 280 m/a 13C NMR Spectrum (50.0 MHz. CDC!3 solution) 200 160 120 80 40 O 5 (PW!) 1H NMR Spectrum (200 MHz. CDC!3 solution) UUIIIIIIUII rUIlUlIUllll uroups Bond Functional Group C-H (1 zoom ('10 II II III 022 2 Q C Alkane -CH3 _CH2_ Alkene Aromatic Alkyne (terminal) Aldehyde Alkene Aromatic Alkyne Aldehyde Ketone Carboxylic Acid Ester Amide Anhyd ride Acid Chloride Alcohol, Ether, Ester, Carboxylic Acid, Anhydride Alcohol, Phenol Free Hydrogen—bonded Carboxylic Acids Primary and Secondary Amine and Amide Amine lmine and Oxime Nitrile Nitro (R-NOZ) Chloride ,‘x rfirknvulir tat-it" \ 8 Frequency in cm'1 (lntensity*) 3000—2850 (5) 1450 and 1375 (m) 1465 (m) 3100—3000 (m), 1000-650 (5) 3100—3050 (s), 900—690 (5) 3300 (s) 2850 and 2750 (w) 1630 (w—m) 1600—1475 (w-m) 2150—2100(w—m) 1740-1720 (S) 1725-1705 (5) 1730—1700 (5) 1750-1730 (5) 1670-1640 (5) 1810 and 1760 (s) 1800(5) 1300—1000 (s) 3650—3600 (m) 3500—3200 (m) 3300—2400 (m) 3550-3060 (m—s); 1640—1550 (m-S) 1250-1000 (m-s) 1690-1640 (w—s) 2250-2240 (m) 1550 and 1350 (S) 800-600 (5) * s = strong; m = medium; w = weak Typical Chemical Shift Values for 13C NMR W"“"" ' fiWfii‘rfiaTe‘é‘Vifue Alkane 6 0 — SO Alkyne 6 70 - 90 Alkene 5 100 — 150 Aromatic 5 110 - 150 Nitrile 6 115 - 125 Carbonyls: Anhydride 6 150 — 17S Ester 6 160 - 175 15': _ 1R0 Typical Chemical Shift Values for 1H NMB_ Type of Proton Approximate 5 Value Alkane methyl: (RCHg) 0.9 Methylene: 1.3 (R2CH2) Methine: (RBCH) 1.4 Allylic: (R2C= 2 CRCHR2 Benzylic: ArCHR2 2—3 Ketone: RCOCHR2 2.1 Alkyne: RCCH 2.5 a to Nitrogen: 2.5—3.0 R CHNR .Z 2 Halide: R21:HX 3-4 a to Oxygen: 3—4 RECHOR Vinyl: R2C==CHR 5—6 Benzyl: ArH 7—8 Aldehyde: RCHO 9-10 Carboxylic acid: 10—12 RCOzH Amines: R‘ZNH Variable: 1-4 Alcohols: IROH Variable: 2-5 Phenols: ArOI-l _ ‘_Variable; 4-7 ...
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