Exam3SOLNPRACTICE

Exam3SOLNPRACTICE - Quiz 3 Chem 261, Prof. Brookhart April...

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Unformatted text preview: Quiz 3 Chem 261, Prof. Brookhart April 19, 2007 Last Name: (PRINT) 1 g E Y First Name: (PRINT) (45 pts.) I. Predict the major product (or products) of the following reactions. Carefully indicate stereochemistry for problems marked with *. H10 1. HI C 3 W CH30l| cH 2. 8’ . t—BuO‘Na+ r ——————> v t _ t—BuOH CHIGr 3 MTV 5 DMSO ' CH3 cu Lu l 9.. . 3 J a! 4 (ch3cnz);cvw I_12() * = c 3 ———————7 Q— S'hon'l a“ 6" I H 6H,“?! ’ ’ ‘ + 2 mm 5cm 7 *5. 075 CH3S' Na+ 3 —————> acetone ‘u CW’ /3' I + at. D *6. a t—BuO‘Na cg \ ,. / —-—- m. -———_—9 ' —‘ (“3&9 C'\ D t—BuO ' /C c. \In! H H r (*5 0H A pyridine u -— S II (.143 -. leJINL: | o ) a .. 9. 00-013 @011 + 01,1 0 8. CH3—CH2—OH c H, cuf— OT: 0 _- a T5 HI (1 equiv.) fl . QH 9H - H109 ‘ 11 10. CHg—CH—CH—CH3 5-) C H} - c —H 11. oH H2Cr04 I ,0 H acetone7water ! . a EON-l :I O _. x H __——————>' u *12. “3C 4“ H“ " w: 2 “'3 cu; m, ' o 13, O I 1)HC-=-C:‘Na+ 9 V H » L§< 2) H20 " 3 I]? b H o + - OH 14. CH3OH/H _/_ >< d—————> I 6 I! i H 0055 OH 015 I ' *1 . ‘ ‘ ,. — ' + ' '- 5 HWC’C;H t BuO Na (lequlv o I “*3 CH3 (12 pts.) 11. Show how to accomplish the following conversions using a sequence of reactions: ' From ' 19 U M Of M\ Kr .4 “0- NQ+ 0H m /\)\/°’J ') 31, "L b 0“ Hm ' mom, 1 mo ( «Mm (12 pts.) 111. Write a detailed step-by-step mechanism for the followingreactions. Be sure to clearly show key intermediates. CH 0 CH3 CH3 I ’39 Ha, ‘ \ 1. CH3—('3—Br ————) CH3—(g—OH + IC=CH2 (8pts.) IV. Order the following species with respect to nucleophilicity (1 = most nucléophilic, 3 = least nucleophilic) Pay attention to the solvent. 1. C1‘ vs I- vs Br‘ in CH3OH @CD@ 2. H20 vs ‘OH vs ‘SH in H20 (96) 0) 3. CH3O’ vs CH3Se_ vs CH3S_ in CH3OH G) 0) (1) "G9 4. ‘OH vs H2N: vs HS- in DMSO 69 CD CD (8pts.) V. Consider the following reaction: H o (CH3)3 C—Br —“——-a (CH3)3C—OH + (CH3)2C = CH2 1 A I B 1. The rate depends only on the concentration of 1.@or F ( Tm 0* 5'“) 2. IF NaOH were added to the solution, the ration of B/A would increase®r F 3. The transition state for formation of A is the same as that for formation of BLT)» F 4. If the concentration of 1 is increased, the ratio of A/B will increase. T 069 ( 10 pts.) VI. Suggest the most likely mechanism(s) for the following reactions (SN,, 8N2 E1, E2). You do not need to write the products. 1 . CH3—CH2—Br N3— acetone 5N1 2. (CH3)2CHI t—BuO'Na+ E t—BuOH 3~ 3. CH CHI HO ( 3)2 _ 2 >1 5”, E) I 4. (CH3)2CHI CH3S‘Na+ 9 5‘” acetone 5. 0‘ CH ONa+ LS< CH30H ’ 51% (8 pts.) VII. In the following pairs, which compound will react faster under the indicated reaction conditions? 1. (CH3)3 CCHzBI' VS CH3)3C—Br in H20 4:. CH3)3C—Br vs CH3CH2Br in t—BuO‘/t—BuOH (6 pts.) Bonus Compound A reacts very rapidly with water to yield alcohol B with retention of configuration. Compound B reacts very slowly with water. H H0 H 5: Explain why A reacts to yield B with retention of configuration and why A is so much more reactive than C. ' A a h” 44., «(fro‘ola‘lo Siemchemzi’cv; 'For nubkbofi? .lM/iiq'llul I4 chlohzlb(PAchn:Lo TM lingul ‘HH will 1"" 7)» OWN“ (In? (“heir-HM in )‘v dHach). C- alm m'l'. aHaokc-I “no! arena! From WW “aka-26 ‘Ilo rcttniu'J. Q inmnm {A LrIA HM). " n. w n . ( ____, t [4,.6: -———-1~ (a T [to ‘ 0kg“ bukm 4W9 :Hw ...
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This note was uploaded on 03/21/2008 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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Exam3SOLNPRACTICE - Quiz 3 Chem 261, Prof. Brookhart April...

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