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Past Exam 3 Ans Key

Past Exam 3 Ans Key - 60.0000 0 Name nflmflgr 6%3 ID...

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Unformatted text preview: 60.0000 0 Name nflmflgr 6%3 ID# Please check here if you do NOT wish to have your exam returned in class. Exams not returned in class can be picked up individually at my office during office hours [Kolthoff 455). Exam III Organic Chemistry 2302 Fall 2008 7 pages including Periodic Table and Spectroscopy Table Do not open the exam until you are asked to do so. Have your ID visible on the desk beside you. Place your last name on all subsequent pages in case pages get separated. You may Hm use calculators, models, or any notes for this exam- Raise your hand if you have a question and a TA or I will help you. Exam begins at 9:05 am. and ends at 9:55 am. When time is called by the TAs, all pens are to be down and no more written work done. TAs are authorized to deduct 5 points from the exam of any student that does NOT following these rules. Read all questions carefully and be sure to answer each individual question. Circle only ONE answer for multiple choices type problems for full credit. Good luck! 1) 2) 3) 4) 5) Total I 25 pts f16pts K36 pts /15 pts f 8pts 1100 points Last Name 1. Consider the structures of Monensin (A), a naturally occurring antibiotic used as an additive in cattle feed, and LSD (B), a hallucinogen. For monensin, identiiy each functional group (center carbon indicated by an arrow) as an ACETAL, I-IEMIACETAL, or ETHER by placing the word in the box. For LSD, similarly indicate the nitrogen functionality as a 1°, 2°0r 3°, AMINE or AMIDE. Then circle the MOST BASIC of these nitrogens. '? pts 002H OH A. Monensin 2. For each pair of compounds, circle the structure with the MOST acidic hydrogen. 6 pts 3_ COZH COZH b. ' O c_ Br 00 H N r: 3 be we“ ob 2w 0 O 3. For each compound below, give the two products that would result from acidic hydrolysis using acid and excess water (H, H20). 3 : Y/\L0112pt5 a. 9(1: D hydrolysis }' H +6” I s o 0 HO b. H hydrolysis ..., NA — SAD + 9:sz «i- Z- c. hydrolysis V\CEN mCDzH + H3): +l + 2.. 0 d hydrolysis D C! Q/ 4- l + 2.. 25 pts Wissinger, Chemistry 2302, Fall 2008, Page 1 Last Name 4. Mechanism — Write a complete mechanism for each reaction below. Use correct arrow notation, and show all intermediate structures and all proton transfers. F” 8+0“8q\ UQcLA-L. 7pts ® ca vbnm \ am 1 “a b. (Be sure to show movement of ALL electrons and bonds broken and formed) 3 pts H C... ",CH 3 N 3 heat 1‘. I ‘L —D- a 2. 6' 5. Contrasting Reactions — Write the product of the reaction of the center molecule with each reagent — one to left and one to the right. If ortho and para products are formed, draw one and indicate the other is possible as in “+ ortho ”. a. 6 pts /‘~ H'N0H3 o HEN,CHZCH3 AN + /l\‘ 1) NHZCHa, pH4.5 ‘CH20H3H \ —h- \ _ "\f‘ v 2) H2. NI Na(CH3002)3BH 16 pts Wissinger, Chemistry 2302, Fall 2008, Page 2 Last Name b. M» 6 pts 1 9. 1A 0 [\f 0 w 1) HzNNHz. WH Zn(Hg) \\ OX“? 2) KOH. heat O\_/0 Wang?“ 6 s+odoiLT6 but. (Wolff-Kishner) (CI mmensen) and NH A 2 1) H3C Cl 1) NaNOz. HCI Ah v 2) AICI3. 012 2) CUCI 6 pts HLOl-l \rkch NaBH4 1 eq 32H5 r; “"01 MeOH ‘ ,- 0 ”V 6 pts (‘3 1 SOCI CH N K AMMOA ) 2 OHAjLOH 2 2 /\/\ 00.13 (diazomethane) 2) Ph/\ 6. Give products of the following reactions (2 per line each going to the right): . (11R 0’ 6pts : “M... NY“, 2) H20 wag“: : N\c heat PK : “5 m3 : (Cope Elimination) \(ma (EN hot, concd. ( 0 i (5 HO‘~/\0H u KMN04 \iou . ‘— : stOH. remove water A _ NGK Lo 36 pts Wissinger, Chemistry 2302, Fall 2008, Page 3 7. (350% Last Name Synthetic Transformations — Show how you would accomplish each synthetic transformation using any reagents or organic materials necessary. 6 pts CH3 0—/ H4») “O’CHLCA'B L“ H39) 93' +l +1 \LHBr (Dwain © ROG-“LL“; /_\\< LDMSO ,C‘Hah’ \ Br- -_'_7 :/ © CO; \v COLA \ G) “50+ 1-\ +2. {9 KCM ® H 9 pts i1 NHL. NC" 0%: ("Z”) pol as 30ml “’7 W‘l‘lfi ej- incl Salli-“lent“: 9. 15 pts Wissinger, Chemistry 2302, Fall 2008, Page 4 Last Name 8. Two isomeric compounds A and B have a molecular ion peak of 121 in the mass spectrum. (What does this imply?) Their [R and 1H NMR spectral data are given below. Use this data to suggest structures for the two compounds. Full credit will be awarded for a correct structure in the each box. Partial will be given for correct conclusions derived for the data given, starting with masss ectrosco . ' *‘ P W Odd 1* Nitroéen ”\> Spts Compound A (W 12114/ Comgound B [NF 1211 . t‘ +1 IR: peak at 3310 cm 4 C 20 WW" IR: peaks at 3430 and 3350 cm "I C I 0am inc.) ' H NMR or} ‘ H NMR 13 (5 H, singlet) ’ 7.0 (2 H, doublet 3.9 (2 H, singlet) 6.8 (2H, doublet 2.5 (3 H, singlet) 3.6 (2 H, broad singlet 1.4 (l H, broad singlet 2.6 (2 H, quartet 1.2 (3 H, triplet 4 THE END 8 pts Wissinger, Chemistry 23 02, Fall 2008, Page 5 ...
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