CHE201B - Quizzes 6-9

CHE201B - Quizzes 6-9 - Chemistry 201 Quiz Six Name 1 Give...

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Unformatted text preview: Chemistry 201 Quiz Six October 23, 2001 Name 1. Give an R or S designation to the following molecules (6 pts). H ,SQH ISHZ 9H3 0 HO>(;>—I H»(;:<CH2CH3 SH CHZCl 2. Rank the following radicals from least to most stable and briefly explain your rationale (1 pts). CH3CH2- (CH3)3C- (CH3)2CH- 3. Give a detailed mechanism for the halogenation of the following alkane. Show all three steps and the expected product (5.5 pts). 0—3;» Ch emistr’y 201 Quiz Six October 23, 2001 Name K? \E 1. Give an R or S designation to the following molecules (6 pts). ‘1‘ 1? l c H E‘OH ISHZ ~ A 9H3 L) 11 0 C HQ>(:2-I A H-C:)—-CH2CH3 ‘ SH ‘ CHZCI 5 E R ” R 2. Rank the following radicals fi'om least to most stable and briefly explain your / ' 3 WK1795 (g/LL CH3CH2- (CH3)3C. ' (CHBhCH. « ‘ rationale (1 pts). , r l , 4 57 a v 'l’(é L, ‘V/L/C i /// mg I. ‘ f . a ‘ u I “ I! ‘/ f I . ” I (f? 'U 15‘ '1 “é fi‘ > CH; w (H; > CHE U“; //u mm cz.{,/:7‘// / / - ~ ' l is” z. ( Pk kc ._,( [LIL/[f f; Iffl/ "1/ f V [m .J/zc 3. Give a detailed mechanism for the halogenation of the following alkane. Show all =3 " three steps and the expected product (5.5 pts). 1 _ /’/ . 5QW“74mw . a,“ 1/ (1/ <> 4% UV V .1 K. m4.“ 7» C/wc/ 4%” 3L! Chemistry 201 Quiz Seven November 1, 2001 Name 1. In the reaction shown below both the reactant and product have an R configuration, yet opposite optical rotations. Are these results compatible with what is known about the configuration of a molecule and its optical rotation? Explain your answer (3 pts). H H Ho»cl'<-CH=CH2 flfl—PL Ho—(;:<CH2CH3 CH3 CH3 R (+) R (-) 2. For the structure shown below draw all of its possible stereoisomers and give the stereomeric relationship between each of the isomers (5 pts). CH3 OH | l HO—CH—CH—CH3 3. Give the stereochemical relationships between each pair of isomers (same compound, enantiomers, disastereomers or constitutional) [4.5 pts]. CH3 CH3 CH20H CHZOH CH3 CH3 H OH Ho H H OH Ho H H OH H OH H OH Ho H H OH Ho H Ho H H 0H CH3 CH3 CH3 CH3 _ CH3 CH3 4. An aqueous solution of pure stereoisomer X of concentration 0.10 g/mL had an observed rotation of —300 in a 1.0-dm tube at 589.6 nm (the sodium D line) and 25°C. What do you calculate it’s [on] to be at this temperature? (3 pts extra credit). ‘ A” I cu»: cg: t 7151/ " M ” a]? f :57 (FCC / Macy I" rm /’,,7 dill/2‘ [M71 izflaéfll'VA/Q/ ’1 m" 3 (LIZ, Chemistry 201 Quiz Seven November 1, 2001 Name [(6’ K! 1. In the reaction shown below both the reactant and product have an R configuration, yet opposite optical rotations. Are these results compatible with what is known about the configuration of a molecule and its optical rotation? Explain your answer (3 pts). HO>C|<CH=CH2 4—1» Ho-$-CH2CH3 CH3 CH3 R(-) Wéj R (+) i (I ,%1 (0’1 [/ 1C 0&7 (“lazy/{7 M7tl/Déc’7’ 1(5) . 5‘” /’O _ ./ . xxx/4 fl%<4* 2. For the structure shown below draw all of its possible stereoisomers and give the yes. , fl; stereomeric relationship between each of the isomers (5 pts). . €43 CH3 OH 6% “’3. ,y 0% | I M, y mid ,’ H Ho—CH—CH—CH3 HO ‘ ,, ,4 OH m C” , 3 xrémflvfl (#3 W’ t A g 4 / (1%”) I 1M Sierra Mrs f 3. Give the stereochemical relationships between each pair of isomers (same compound, enantiomers, disastereomers or constitutional) [4.5 pts]. CH3 CH3 CH20H CH2OH CH3 CH3 H OH Ho H H OH Ho H H OH H OH H OH Ho H H OH Ho H HO H H 0H CH3 CH3 CH3 CH3 CH3 CH3 5mm COW/wuflx f “M mng duwié/lxoW/so 4. An aqueous solution of pure stereoisomer X of concentration 0.10 g/mL had an observed rotation of —30° in a 1.0-dm tube at 589.6 nm (the sodium D line) and 25°C. What do you calculate it’s [Ct] to be at this temperature? (3 pts extra credit). - 30 O } M (ad) .. ._-' M " Zak-j ¢ 5a Chemistry 201 Quiz Eight November 8, 2001 Name 1. Complete the following reactions (4.5 pts). CH3 A. .21, heat [CH3 B. QCH=CH—CH2CH\ 113i, CH3 CH3CH2\ [H + C. /C=C\ __Ii‘=g_* CF3SOZO H CH30H 2. Using the following reactions to compare and illustrate an SNl and SN2 mechanism, and give the corresponding product to each reaction (5 pts) CH3 Br CH3CH20H A' solvent CH3\ _ B. CHCHZCHZBr M CH / 3 3. For each of the following circle the stronger nucleophile and briefly explain your choice (3 pts). A. CH3NH2 CH3NH' B. CH3OH CH3NH2 C. H28 H20 H2 Se Chemistry 201 Quiz Eight November 8, 2001 Name Km 1. Complete the following reactions (4.5 pts). CH3 0’ 3 ’3" )/ heat ‘A At / /CH3 / , 0/ = 0/ “CH —— C" B. CH=CH-—CH2CH\ NBS \ , \ (#3 CH3 CH3CH2\ H + «1/ ("if A? c. /c=c: _Ag_, ‘ *3 2\ _, {6/ CF3SOZO H CH30H f \ fl CHM 2. Using the following reactions to compare and illustrate an SNl and SN2 mechanism, and give the corresponding product to each reaction (5 pts) (its Er ('HV3\+ /\ CH3 Br \ Stow Cifiaéé/f, ' CH3CH20H mm» \/ ,, . SW! A' solvent “ts \; /‘°(’// {/C’ /\ \7/ CH3\ _ g N 2, B. /CHCH2CH2Br M CH3 j; L‘f/z [(#3) Z 1 w ‘4 ‘/ Cllé\ , (A 7’ CW M ‘c ’zzi- AA (#~(H?[//147( 2 /5 H “ U (#3 / 3. For each of the following circle the stronger nucleophile and briefly explain your choice (3 pts). A. CH3NH2 B. CH3OH CH3NH2 J AM (,Az:,z¢m,4{m/M C. H28 H20 ' Va Jpwlz‘ Z/a/flri’jzz Chemistry 201 Quiz Nine November 15, 2001 Name 1a. Using the Cahn-Ingold-Prelog system of nomenclauture to indicate whether the following alkenes are E or Z [show your work] (3 pts). CH3CH2CH2\ IH CH3CH2\ [H C=C C=C H’ \C H3 H3C/ \CH3 A B 1b. In Question 1a which alkene, A or B, is more thermodynamically stable, and give a rationale for your answer (2 pt). 2. Complete the following reactions (4 pts). 3le A. QCH—$H—CH2CH3 CH3CH20_ Br e13 B. QCH—CIIH~CH2CH3 (CH3 BC-O' Br 3. Indicate how each of the following reaction conditions will affect an E2 and SN2 reaction mechanism (3 pts). A. Base Strength B. Solvent polarity C. Size of the Alkyl Halide (steric hinderance) Chemistry 201 Quiz Nine November 15, 2001 Name K 8 1a. Using the Cahn-Ingold—Prelog system of nomenclauture to indicate whether the following alkenes are E or Z [show your work] (3 pts). H CH3CH2CH2\ : /H L N CH3CH2\ ' /H L /C‘:C\ H CH3 H L H3C CH3 N A B ,/ 1b. In Question 1a which alkene, A or B, is more thermodynamically stable, and give a rationale for your answer (2 pt). fii’ w Jflfzc leak ‘ /] ([4,; HQ LIZ I“ [it "Side/13' CL,(/;',Y¢:/‘_¢ . 2. Complete the following reactions (4 pts). A. ©CH—$H~CH2CH3 CH3CH20' \\ {/“LI'ZZC/f'f/Q (7713, Br “a” B CH3 CH CH CH CH CO‘ /:\ Cry 0/ 0/ CI/ . — — — "" I : ’ ’ ‘7 1‘3 2 3 1‘29 \\,.L/' I 1‘ . 3. Indicate how each of the following reaction conditions will affect an E2 and 8N2 reaction mechanism (3 pts). A. Base Strength S~—lr’f‘:’}/‘ Arc/£71 /{’~w’~’/’S E B. Solvent polarity M74 7754,2215 T/Z/K'l/b") A /’ i C. Size of the Alkyl Halide (steric hinderance) ’ raj/ML; 44/2112 4%" 47’“? 71 ’0) 7/ H'YM’C /. (f 4 ...
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CHE201B - Quizzes 6-9 - Chemistry 201 Quiz Six Name 1 Give...

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