MS E2 Fall 05 - ”sewn,” mwnmwwmmwmmWW-pm Wiwrmmwm $...

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Unformatted text preview: ”sewn,” mwnmwwmmwmmWW-pm Wiwrmmwm $ CHEM 241 (Dr. Montague-Smith) Organic Chemistry II D5 Examination ll 1 November, 2005 YOUR NAME (Last, First, MI.) DISC SSION SECTION #91 _________ (3 points) Initial of last name Instructions - Please fill in your name in the space above 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 on the f_o|lowing 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 INSTRUCTEID 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 rovided uestions in the 3 aces - Answer Name CHEM 241 Exam ll 1 November, 2005 Notes ° This exam is worth 150 points - The exam period is 115 minutes. At the end of 115 minutes, all exams will be collected in a timely fashion; there will be no exceptions; University Honor rode Acknowledgment I certify that l have neither given nor received assistance of any kind in the completion of this examination. Correct Section No. Problem 1 (PART A) Problem 1 (PART B) Problem 1 (PART C) Problem 2 Problem 3 (PART A) Problem 3 (PART 8) Problem 4 Total Signature Points _- (3) _ (20) __-(2‘0) _____(20) .____(20) ___(25) __.._-(25) _ (17) ____(150) Exam Begins On Next Page V‘VUQMWwMHWWWWV—w «am mm mwm «WOW mavewmwiwmquuimmmmwsmummw 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 equilibrium reaction, assume product formation. PART A OH O /‘L\ ———-——-> + OH H3O OTMS 1) MgOIEther |/\/ 2) Formaldehyde 3) H30+ \AOH 1) LAH 2) Acetone/H+ :1 mm, 2) H2N-NH2/OH‘/A 1) DlBAL NH 2)/\/ 2M Problem 1 continues on next page OH - wmwmmmmW—Wmmm mmmmm vmmm»mmmmu “Wimnmm-muummmm inmmwmw Problem 1 - Continued PART B 1) FCC ——————————-> 2) HN: > /H+ OH 2) NaOH/HQO W H+ -——-—-—-——> OH O .___1_)_03______> 2) NM 3) NaBH4 4) H30“ MgBr 1; Goa gs) 2 3) H30+ Problem 1 continues on next page Problem 1 - Continued PART C Br 1) P-(CesH5)3 2) Butyllithium 70:0 /\/\ 1) NaCN Br 2) LAH ’ 3) H30+ HCN /\n/ —-———-—-————> O \ N H30+/Heat ——-———> OF NaOH/HZO -——"——> Br HMWWNWNM“W, awn-mmm m...mummuwwmmmmuwmmmummmmw 2. (20 points) For the transformation below, provide a reasonable synthetic scheme to effect the transformation. if a given synthetic step results in multiple products or multiple stereoisomers, assume the MAJOR product or isomer you wish to proceed with can be isolated. Hint: Protection! 0 O O mmww ngwmwww WWflkfl. , ._,.. ,N. .m, , 3. (50 points, 25 points each: For the transformation below and the one on the next page, provide arrow- pushing mechanisms. If Intermediates occur which are stabilized by multiple resonance forms, show all resonance forms.. PART A. For this mechanism problem, it is acceptable to use "H+" as the proton source, and ROH as the base in deprotonations. O O H3O+ HO OH ._______________, \/\\/ \/ ............... :vmmmeWmMW-kaw ww»w.mg«~sum:mmmmus”mmlmwmnw”maymw‘ummwwmmmmwl PART B. For this mechanism problem, it is acceptable to use "H+" as the proton source, and H20 as the base in deprotonations O N H /\/\/“\ H30+ \ -——-———-—> H2N H 4‘. (17 points) Using the spectroscopic data provided on the next page, determine the structure for the unknown molecule. Draw your structure in the box provided below. Table of IR and NMR information is at the end of the exam. Draw your structure in this box ruwmm—thwflm —. w... we! «mum mam-waw We! mm.«’1‘vamemmnm9mmmmwuwn~mnmuPM“. Wm. “mm"flm.mflhm~m ,, , 40003000 13C NMR Spectrum (50.0 MHz. coo:a mutton) 1723 th—IJI—h—K— 2000 1600 1200 800 V (cm") Mass Spectrum 105 120 100 200 240 280 WWW—fi— 1H NMR Spectrum poo MHz, com, mluflon) ,,_-_ —~« .. -.mmfi~wmmn—‘ mmm” W mtwmmIQO-Wm mums- -- ”W.” typical lH Absorption Fro uencies for Bond C—H 0 ll ('1 i”? 00 C-0 0-H i Z n ZIPOU 022 i Q Common Functional Functional Group Alkane —CH3 _CH2_ Alkene Aromatic Alkyne (terminal) Aldehyde Alkene Aromatic Alkyne Aldehyde Ketone Carboxylic Acid Ester Amide Anhydride Acid Chloride Alcohol. Ether, Esterl Carboxylic Acid, Anhydride Alcohol, Phenol Free Hydrogen—bonded Carboxylic Acids Primary and Secondary Amine and Amide Amine imine and Oxime Nitrile Nitro (R-NOZ) Chloride roups Frequency in cm'1 (Intensity*) 3000—2850 (5) 1450 and 1375 (m) 1465 (m) 3100-3000 (m), 1000—650 (5) 3100—3050 (s), 900—690 (s) 3300 (s) 2850 and 2750 (w) 1630 (w—m) 1600-1475 (w-m) 2150—2100(w—m) 1740—1720 (s) 1725—1705 (s) 1730«1700(s) 1750-1730 (s) 1670~1640 (s) 1810 and 1760(5) 1800 (s) 1300—1000 (s) 3650—3600 (m) 3500—3200 (m) 3300—2400 (m) 3550—3060 (m-s); 1640—1550 (m—s) 12 50-1000 (m—s) 1690-1640 (w-s) 2260-2240 (m) 1550 and 1350 (s) 800—600 (5) * s = strong; m = medium; w = wea “~—\ 5 \, 5 Typical Chemical Shift values for 13C NMR 3 W" “ ’ Alkane Alkyne Alkene Aromatic Nitrile Carbonyls: Anhydride Ester Carboxylic acid Ketone or Aldehyde ‘ Approximate 8 Value 6 0 - 50 6 70 - 90 6 100 — 150 6 110 — 150 6 115 - 125 6 150 — 175 6 160 - 175 6 165 — 180 6 180 — 220 Typical Chemical Shift Values for 1H NMR__. Type of Proton Approximate 6 Value Alkane methyl: (RCH3) 0.9 Methylene: 1.3 (R2CH2) Methine: (R3CH) 1.4 Allylic: (R2C= 2 CIRCHR2 Benzylic: ArCHR2 2-3 Ketone: RCOCHR2 2.1 Alkyne: RCCH 2.5 a to Nitrogen: 2.5—3.0 RZCHNR2 Halide: RZCHX 3—4 a to Oxygen: 3—4 RZCHOR Vinyl: R2C=CHR 5—6 Benzyl: ArH 7—8 Aldehyde: RCHO 9—10 Carboxylic acid: 10-12 RCOZH Amines: RZNH Variable: 1—4 Alcohols: ROH Variable: 2—5 ”Phenols: ArOH ryariaolwe: 4-7 ...
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