040318 - NAME CHEMISTRY 109B(B.H Lipshutz Final Exam 10x6 3...

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Unformatted text preview: NAME: CHEMISTRY 109B (B.H. Lipshutz) Final Exam March 18, 2004 10x6 3+4+3+5+6+10 15 15 5x5 10+8+6 6x5 extra credit 60 31 15 (h) (i) 1. Predict the major organic product from each of the following. Indicate stereochemistry where appropriate. 3. NM! C52 002Et L .____—____._______.—.._.) 5 ‘OH Maj, A H30’ , rt 1,6xaws EtLi, 0 .—.__—__———_——.——fi Z. 3. Zn/HCI , A COgH 1.4fi2fi L6H ____—___.._—._——__q 2. VVarkup 3. A020 >©=O N | H I. 2. W13? 3. 18m, m H* I. n’BVLI I TN"? __ 2. >”V”‘Br H "‘ H a. LDA 4. my . 5. H1, Poi/64504,] gum. EWH, Cm‘. H+ m 0H 2. OEt Wm H // ‘- NQOH’. ”WI-W. 2. Collins 0116(6hW __________________, 3~ HZNNHPh, [M- H’ l- H3”, H+, (47/0 2. MaBH¢ 3. 17090! , 93rd 2. When ketone 1 is exposed to certain reaction conditions, trideuterated derivative 2 is generated. Alternatively, treatment with LDA and then MeI gives a different product 3. H D 1. LDA, -78°C *— ‘ —._—> D 2. Mel Name optically pure starting material 1. Draw 1 in a 3-D representation. Provide the reagents / conditions needed to convert 1 to 2 (over the arrow above). Suggest the structure for product 3 (stereochemistry!) (in the box provided above). Treatment of 1 with MCPBA gives product 4. Suggest a structure for compound 4 (in the box provided above). Provide a mechanism for the conversion of 1 to 4. 3. Starting with acid 5, devise a synthesis of chloride 6 using any reagents of your choosing. l UCOOH steps Oé\/ ——————-—-—-—> 5 6 4. Starting with alcohol 7, devise a synthesis of methamphetamine 8 using any reagents of your choosing. [Hint recall that it is easy to go between various oxidation levels, and so, think beyond the obvious that’s given]. a}: steps m ——————-——> HN \ 7 8 5. Starting with cyclohexene, predict products A through F that accommodate the chemistry and molecular formulas provided (place answers in the boxes). 1. Mg HBr 2. CO MeOH 3. H30+ cat H+ (CBHHBr) (C7H1202) (CsH1402) 1. LAH 2. workup CH3COC| E <———-—— D Et3N (C9H1602) (C7H120) a E E E E 6. In an effort to perform the haloform reaction, ketone 9 was treated with > 3 equivs I2 and > 4 equivs hydroxide, but none of the expected two products were isolated after workup. O excess I2 ——_—> NO haloform products , excess HO 9 H20 (a) Provide a brief explanation as to why this reaction failed to go as planned (z'.e., to give haloform + another product). (b) Suggest what the actual product(s) would be from this reaction. (c) What are the ’expected’ two products in any ’haloform’ reaction? 7. For each of the following. Choose the answer (A, B, C or D) that best fits the Chemistry to the left. Place your selection in the box provided. the strongest acid 0“ G) ’ NOT a speCIes formed 0_( ”A 0% doliring the saponification m0” A A F @H; We” we” unreactive toward ; fir w a CI cyanide ion W XV make 3 MT. fill and + M. #3044 lb: ‘ ”gm 0" C411 WNW Hv/VOH crucial in dad aim/m am organic "Schotten-Baumann" aqugaus ”($95 and M salt/emf . conditions '— hydmvlde q/mlm MM bmnldés rmsabu tum» water cannot undergo . H0! racemization ‘ ~“ M/ i M3 i— \%W \ l4 - Extra Credit (”Money” Question) 8. When ketal 10 is treated with acidic methanol, product diol 11 is formed. When the Z- isomer of 10, ketal 12, is treated under identical conditions, product 13 is obtained. 02MB 02MB MeOH ———> 0><0 cat H+ HO OH 10 11 f—Fcozm MeOH / OH O><O cat H+ 0 13 12 (a) Explain why totally different products are formed, when the only distinguishing feature is the stereochemistry of the olefin in each starting material. (b) Provide a mechanism for the conversion of 12 to 13. (c) Name the functional group associated with the ring in compound 13. (d) If the solvent is‘ changed from MeOH to ethylene glycol (HOCHZCHZOH), does the outcome (126., products 11 and 13) change for either reaction? Explain. ...
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