Chemistry 345- Zimmerman- Exam 2a- Fall 02

Chemistry 345- - Organic Chemistry 345 Fall 2002 Exam 2a Question 1 2 10 11 12 13 Points «p Name(Please arite Clearly#— Student ID Fathergs Name

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Unformatted text preview: Organic Chemistry 345 Fall 2002 Exam 2a Question 1 2 10 11 12 13 Points «p Name (Please arite Clearly) #— Student ID Fathergs Name as in UW Records) Seat Number Grader’s Initials é‘gli MS w HEN“! 1‘. (\ 3. NOTE: 2 Pts for each Equation; 4 Pts for each Explanation. 7 7 7 7 77 7 7,7777 77 7 ,77 7 7 7 7 7 7 7 7 7 7 ,7777 7, 7, 7 7 7,7 777 7 7777,,7,77,7 7,7777 2 Fall 2002 Exam 2a — 2 g l m ' ' Maj oi . Name (Please write clearly) 1) Give the products of synthesis as isolated after workup. (a . ' CH: 7*; a) Ph-fi-CHz-fi'CHz-CHs 1’ 2 KNHZ’ “‘4 “H3 pt -9. mm Jam} 0 o I 2) Benzyl Bromide 0 0 p-Methoxybre’ zaldehyde + Diethyl Malonate Mu) CH =4 (£00 Et. L b) “I‘l’ . EtzNH EtOH )2 ’l/ x v CHJCLOOEt)l o f— (9 K1} PhCHZCHz—NMeZ m 9km; c meg I9 A; d) file 0 2/ N N :7. o ‘N ' /[/ B G + Q NaOAc Q). N O O I ‘ r , ) /COOMe - $31.?“ 3 1 N OM ,EtB 7 . .u— @. Me-CH ——————>) a e' r CH§WR 'WM f a \ . 2) Dil NaOH A y W, D COOM? .3) A 110 °C . g2 1)NaOEt , _ if: .. - .y L CH3—C-CH2-C00Et "*3 fi “1 .305?“ II 2) Benzyl Bromide o o g) CH3 - CH3 ma. -r 2'. H V :: _ _‘ + __.————-> e r '— A... . (P L M620 CH ("3 CH3 W NaOEt, EtOH ~ 5” x A 3 . o O O v arcane-43) “t9 - we _ _ _ ———-> ' .. ‘P L h) Ph fil CH COOEt D". NaOH Vqu l(TCHa O o _ Phthalimide _7_____> “' N _ n Pr 1) 0 1) KOH, EtOH VP) a?” 2) n-Propyl Bromide - . O luscmu clmloL 2) How do you explain beta-dicarbonyl compounds having a pKa of about 10 (Le. Ka = 10“) while ordinary ketones have a pKa about 20(Ka = 10’”) ? Use Acetone and Cyclohexane-1,3-dione as your two comparison examples.Your answer requires drawing some resonance structures. Draw all which are p0ssible and relevant. i? ' 7, (i (3 CH3 C CH 4“) r _ I; 5%) €53 3 r o 0*- cqb CC!“ “<3 ‘ . . . - q/ ‘3 i; More reSonance Mew“ M0“ 5+“b’l'm‘hml “3'th \ WSW” “r (W 535123): Organic Chemistry 345 Fall 2002 Exam 2a @ 4) Give the products of synthesis as isolated after workup. _ a) c) g) h) i) -5 Number the following in ord 3” Decreasing basicity (1 Least basic, 3 Most basic) CH3CH2CH22‘ i, L ide l . Ph_C_CH2_C_CH3 2 KNHZ, NH3 || 025 2) Benayi Bromide o . a “a . . M +7’ b) ID1methylAd1pate ——————> 51mm NaOMe ‘3 O . 55 fl on Wk 1/ gfi‘Wm l ____———-——_—> Ethylene Glycol, TsOH A fitfb-Ee Ph \ /Me Ph-C-C-S-Me H il AKHQ) O O 1 . Ph-fihxyg’fg' benzene A 0 ‘ P“ O a V CH CH CH COOM ————> 5 3 2 fl; 2 e 1) LDA me V - fie I 2) Me-I g p—Me-Ph-C-NH2 _ P- ypk"N l + ll‘» ~ Neck,» 0 a O 0 « . SQ gghizyl Bromide g? E HE) _ = = ———> i Ph "i/ C O Et2NH fi a Ph\ 1 , C COOEt Et/ ( )2 Urea, NaOEt i) 5) Write out the mechanism of the_(_3urtius - unshared electrons. O .. Name (Please Write Clearly) ' o Ic§§€e -—> PkwcHr—C * \ -... (—9954: iufibcfilql (Leela Organic Chemistry 345 ‘ Spring 2002 ExamZa - 4 Name (Please Write Clearly) 6) Give the products of synthesis as isolated after workup. 0 a) ENj 1.Methyi Iodide & Ma 2. H20 workup 4L 1 b) Ph-C-NH-Et L'A'H4’ Etzo Pk ~ 9H; NH Ei: + O . » M - ‘ 0) Ne CM +1 ——~' 9 CUCN Mc Me p j 1 d) MezC-OOH. 0” :jl dil H2804 A + 05"CMCQ \ . . e) . KNH2 ‘ b “l? Liq. NH3 *N" NH; 3 Cl * is a isotopic carbon; just use the * to designate it in the product. i) Ph-CHz-CHz-CIEH-CHg, Pk ' CHg'CHl" 6” ‘6 H 2 ‘l‘ Z NMe3 OH' , e . / . e . g) . @0\ W62 +2 a (E A _ h) is Br 5’ + L \éj H3P02 Q ‘ M5 Me fin 1 . - p-Bromoamline \l' 2’ u 1) HN02 © . a. 2) CuBr 5‘, o O 3) "J v1 Propionate —-———> H H , Waco, “ _ , .i J V A. +2 J o NaOEt CH3 C‘Hac f” C 95 b It , . away-ct? 0 Bi: CH3 Organic Chemistry 345 , Spring 2002 Exam2a - 5 ‘ Name (Please Write Clearly) 7) How do you explain the difference in basicity of amides compared with amines? Make clear which is more basic and also include an resogance structures needed ' .. _ 9 h 9 . " _ ~ , to explain. H_ N,“ N: . N=M. Audu‘l ' u mv H . a; G basic [£55 bays. L More more, resaxmnce = More sl'ab‘v'i‘h" : [cab 100535;” Which is more acidic, p-cresol or p-nitFophenol? 9-”; M 91mm 1 (ans). Now, 8 ) Draw the resonance structure responsible for the enhanced acidity. 25H ' " 6 H 0H 9 ‘ 3 © ' It <—> ta / 6.. “(.3 CH3 G,é,.&/‘J-_-wo “5'9: 9) > o 0 H II In the Hauser method of selectively alkylating a 1,3-dione as Ph-C-CHZ-C-CHB, draw thtructure and indicate which is the more basic site which thus a ‘ Isalkylated wr (e.g.) methyl Iodide. 3 H _ :7 “H numb“ W37 Pkgkwfgdua 2 , ilk/"C-C‘H ‘C-‘L u "I; ' e i/a 3H on «He 04 hahu’bcph- M wart. l eyfiu.o£ Kuw. M Ma Ott'5°“1’6arbw~§ F5 ramauedv “54"” 2 eQJu‘N’ wbon‘ o-ise Camzs 04:6; 44.: in basicity of p-cyanoaniline compared with aniline. Which is 1.0) Explain the di - ‘* ~ - ,- ‘ more basic , . Now e resonance structure responsible for the difference in o . ' u H. 3 f +1.; H 0,. Ha 'i??u" "Low resonaule = More sulfide} [FF-1 = ‘ ‘ re :5 loads 3 i 11.) An Amine is treated with Benzenesulfonyl Chloride and Sodium Hydrmnd the ' ' r - dissolves to give a clear solution. What can you conclude? You can conclude that it is a (Primary, Secondary, Tertiary) Amine. 501 e a! 12) 0 wish to synthesize mfbromobenzene and have glacetanilide as the starting material. Give a reasonable synthesis. (HINT: Brominate first). HNAC, "NA; "MAL “H: i ‘ airs»! ' 6 , n {’0 W l 3": 3‘ Sr; > er Fag]; 6" “N03 ? g M) Fegf‘g @ Peer; @ . "MH 6 . '5’ er _ . 8r 6r gr 13) What base could be used to prepare LDA from Diisopropylamine? but,“ .‘+L'. um (Butyllithium, Lithium Ethoxide, Lithium Hydroxide) ...
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This note was uploaded on 04/05/2008 for the course CHEM 345 taught by Professor Zimmerman during the Spring '07 term at Wisconsin.

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Chemistry 345- - Organic Chemistry 345 Fall 2002 Exam 2a Question 1 2 10 11 12 13 Points «p Name(Please arite Clearly#— Student ID Fathergs Name

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