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final-key - r'l I"{7"”Callam Chemistry 251 7...

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Unformatted text preview: : , r'l I"\ ,{7 "”Callam _ Chemistry 251 ' ' . 7 Autumn 2903 . 7/- "FINAL ' 300 points ' ' K a Name (PRINT) . E a '- _ I have neither giyen or received aid on this exam (SIGN) ' - Place'an X in the box to the left of your recitation section. Failure to mark your correct recitation section will result in —5 points from your exam total. 1:30 p-m.—2:1 8 p.m. ' 1:30 p.m.—2:18 p.m. Kamala Kunchitha - athatn Kamala Kunchitha - atham 1:30 p.m.—2:18 p.m. ' 1:30 p.m.—2:18 p.m. Will Henderson 7 I Will Henderson 1:30 p.m.—2:18 p.m. ' 1:30 p.m.—2:18 p.m. '- . ; ‘ Amanda Kutney . Amanda Kutney 'T 2:50 p.m.—3:18 p.m. 2:30 p.m.—3:18 p.m - Kamala Kunchitha- atharn _ - _ Kamala Kunchitha-atham 2:30p.n1.—3:18 p.m. ' ' 7 2:30 p.m.-3:18 p.m. ' Will Henderson I Will Henderson" 2:30 p.m.-3:18 p.m 2:30 p.m.-3:18 p.m. Amanda Kutney ' 7 Amanda Kutney °‘ Please }ead all of the-directions for each section of the exam carefully. ' ° There are 14 pages. including this cover pagefor FINAL, please check to make sure you have all of the pages. . Make sure your answers are clear. Any structures or answers that arerunclear or ambiguous are considered wrong. 0 GOOD LUCK! Doyouribest- ' Page 1/14 Callam 'Part 1. Predict the ‘Product(s). Predict the organic product(5) of the following reactions. When appropriate, be sure to . indicate stereochenustry. If man: than one pmdzm‘ 2'1 formzd be mm to indicate the may'orpradwt, zfstmozlmrréerx are pmdymd in fire reaction be mm to indz'mz‘e the mhfiamszb betweetz them. Draw all answers in skeletal form. You will be graded on the product you draw from Chemistry 251 Autumn 2008 7 ethereaction no other information is needed for this question. (6 points each for a total of 120 points) 1. Br2, H20 , _ 2. NaOH, H207 -—-—-—-—h— (0:0 NaCN, '/ ' ” H2304, H2O VNéSH, CHSCHaoH _ -——————-—-—-—h- _ (CH3)3COLi mi.- (CH3)3CHOH Mammy 5 sH Page 2/14 Callam _ , ' Chemistry 25} Autumn 2008 OH _ ' 'ér PM Pk . “‘5 _ c443 , _ _ ‘ . L NaSH d 7 ' 3. CH 030 CH 7: .1 _' _ Br 3 2 3 ' S 1. CHacHzMgBr , _ - ‘ ,3 HCLFbO _ 3:0 mm Page 3/14 Caflam O Q :\ 1. Brz,‘ hV 2. NaOC(CH3)3 Ao’o‘ H H2 (excess), PdlC ——-——-———-—-—-——————)- H2804, CH38H 1. LiAlH4,THF 2. HCI, H20 3. PCC',CH20I2 -——~——w—-—-————-+ 1. Brg, hv, CC!4 2. Mg”, diethyl ether- ' 0 3. VLH -4. H01, H20 _ Chemistry 251 o- :Zl.‘ VI 0“ Oz» Autm'm'i 2008 + WQMHW ' Page 4/14 Callam _ Chemistry 251 1. 3H3 _ 2. NaOH, H202 I 3 PBrS M B If 0C“; ‘ 1. CH3CH20H: H2804 I O 2.- NaH .;..\ _ L ”"0" 0 I NHZCrgo-‘r; H2304. H20 W o 1—! WOH ‘——_"""-_"' 7 1. LiAEH4,THF - I H I >—< —.———-——-——-—§- ' ‘ o .— , 0 V , ' D o ‘ , _ HacJLo’O‘H -- - “‘OH : _ 2. LiAID4 - o 3. H01, H20 . ‘ Autumn 2008 Page‘5/ 14 __ _ Canal - - ChunkuyZSl ' Aunnnn2008 Pat: 2. vaide the Reagent}. . Provide thereagents orstarfing materials to perform the indicated transformations. More than one reaction-may be required. (8 points each for a total of 48 points) - ' - \-Nao—f ' O—Br O—Br 2- - 8 V1" - Er ldkc 2.L:Aqu OH ngCl, H10 0 ' H.NnH .cHst Oo<_-;:% ”‘1me i, - 'z . “a S C Ha .\OCH3 . ' I+SCH3 ' 1 SCH3 , q . M a H ' , . Br 2” 4? ' . E:TATOH Page 6/14 Caflarn CherniStry 251 Autumn 2008 7 Part 3. M cabanismr. Provide a mechanism for 2 of the 3 reactions shown below. Be sure to include all intermediates, formal charges and arrows depicting electron'movement. Be sure to place an X next to the mechanisms that you want graded for credit. If no marks are indicated the first two questions will be graded. (40 points) - a) H2804, heat OH ————————»- , ' 4 ti 02:0 (9 0H HLO‘E‘W I: UAH :9 [ 33. J!“ - H4; -_7 _"—-——. [lb . a b) . _ H20,heat ' _ OW . 0 ++ OOH Page 7/14 Céllam , _ Chemistry 251 . ' Autumn 2008 . MgBr - ‘ 1. [:r 0” OJ . . ' ' _ Part 4. Synthesis. Provide a synthesis of the following alcohol. All of the carbons in the-molecule below must come from alcohols oralkcnes containing five carbons or less. You may use any other reagents that you find necessary. (20 points) \ OH I ¢\, 7 3"2. ' “(ls ' - ‘ Pw 5 W3?- fl'évmfilbv 7 U ‘ PcC h® - SIT/\DH ——-—-.? 9- *"——9' cud/i" I z-Hu'n'w ' HrBV M3” Quin -——-e 3v .___3 Page 8/14 Caliam _ _' Chemistry 251 Aumtnn 2008 Part 5. Explain. Answer 6 of the following 8 questions in Part 5. Be sure to indicate which of the 6 questions that you want graded by placing an X in the left hand margin next to the letter. If no marks are indicated the first six questions will be graded. a. Add Base. Predict the products of the following acid—base reactions. Label the acid, base, conjugate acid, conjugate base. Draw curved arrows to indicate the movement of electrons (bonds breaking and bonds forming) and predict the direction of the'equilibrium for the reaction. 0 H i ‘ (—11- fi b. Resonance. Draw FOUR of the MAJOR resonance forrns for the following molecules shown below in skeletal form. Be sure to include electron arrow movement to show how the electron movement occurs between resonance forms. Page 9/14- Callam - ‘ Chemistry 251 _ Autumn 2008 c. Steteochemistty. For each of the following pairs of molecules identify them as one of the following: constitutional isomers (1), same molecule (S), enantiomers (E), diasteteomers (D), or none of the above (N) by placing the appropriate letter in the space provided. ' - - _ 7 H ' . HO - . HO’ . a) T L , - b) D .' 6‘ - H HO ' . ' OH - , s' - E I d) 5-" RO-Js\/ H OH . 0 OH a . d. Conformations. Draw the two possible chair conformations for the compounds shown below. Given the fad thait the A value for CH3 is 1.70 and the A value for C(O)OCH3 is 1.28 whichconfo'rmationis more stable. L - [- (‘i1_3). I ' ' o 0‘35 OCH3 - V” o 7 , ' . fi Wo/ _ . . "3‘0 _ MR2. 3mm. Page 10/14 Callam . Chemistry 251 ' Autumn 2008' e. Substitution/ Elimination Reactions. Explain why 2-bromopropane gives different amount of subtitution and efilmhation products when'the nucleophile/ base is changed from sodium'acetate to sodium ethoxide. ' V Gin-no new. 0 6 * WEEK. egg-L ’ 1k ‘ N30 1? , . o . ' 5N1... \fl/ O f. Reaction Energy Coordinate Dia substitution reaction. ' grams. Provide a mechanism and reacfi’on coordinate energy diagram for the foIldv'ving Page 11/14 _ EXN Cameo-W44? , Callam ' Chemistry 251 ' Autumn 2008 ‘ g. Reactions of Alkenes. , The following addition reactions of HE: to the alkenes shown below are highly regioselective. Predict and explain the regioselectivity of each alkene; _ HBr " - _ e . / 0\ ' ‘ ' 7 o . Ewe“ W _ ‘ A , 13K -\ I r Agfi: {MWLflw W0\ "£3 -/\®/\"/°\ ' f - BM OPrlLBOCM'IrM-i ‘ ._ D W\ _')‘ o ' ' . ”Kuhn wacky of) Eve . I ' HBr o , (“CREE-1n” O —-—-——-———+ \ 7 __.__, W 3 W @J 0 I I Bxf - - W \ 1L . j M \. , ”CF/10“ e “”6”“- H'Cfiv ‘ ' ave “gamma DI swab “who cal-11M ' - h.‘ Hammonds Postulate. Using Harmnond’s postolate and a reaction coordinate energy dJagram, explain why the follcinving alkene'addition produces? the product indicated. 0/W 045M0- ' '- ‘Br' - a damn 0} 7' .—‘-‘> ,. 00 00 0% 9." c’flRBOC-Mmau 7,0 CHIN/u- E . N _ , VFC/n—rLaocnxnw 5‘ 9 if ' ' _ ' r1 2" CAKBnWHIW ' can, E . it . 6)" - . ,E“ (20,1 30 wine“. Page 12/14 ~———~—a- .——-___~_ Callam . . Chemistry 251 I Autumn 2008 Extra Credit (5 points each) 21) Using the principles of electrophilc addition to alkenes, predict the product for the following addition reactions to aldheydes. ' - (5 points) 0 / ' ' o - . 0 ”“3 / b / CH30H (2 eq.), H2304 H CH30H (1 eq.), H2804 o H ‘ b) Draw the first transition state from question Part 5 f. (5 points) egg 1% " u ‘ a. 3;, H I \- o. I 7 ‘ t? Br 6 (3) Provide the starting material for the following reaction. , _ :10 I 7 1. 03 (excesS) ' ' . ‘ 2. CH3SCH3 9 ' . 1.: O - Page 13/14 Callam I Chémistry 251 ' Auturhn 2008 Periodic Table won carbon 11an «my: Mum» anon ' 5 ‘6 1" B 9 10 0 e 55.11 12311 141001 153“ mm .1113 _ mrfium men mm sum- Wu: lawn 13 14 15 1E 17 1! i . - A. S! Ar 26.382 2/8386 302'“ 52585 35133 ' 39MB rldm 150mm 211: cairn «1mm maria «lulu: bmmne W 23 29 30 31 32 33 M 35 35 ”5'33 Ssfifl “5H 6:! ' 59.723 ~”.51 1mm - n96 mm: “50 “mm palladium m mun: . mum lsn anfimny Warn Mm acme 45 ' 45 ‘ 47 4B 49 50 51 52 51 54 film! . 409% 151.!" 112.11 {1432 (18.1! 121." 92160 126.9!) mean: .c‘ 1. am 79 88 76 TB 83 mm mm m m 109 119- 111 u .11 r a" mph: want-aim terbhm urn-prams: .m 63 62" 57 637 as in m 5:3 Gd Tb Dy'Ho Er Tm Yb £57.25 15633 $62.50 154 .83 187,26 Ev! .93 ' l '- ' mm mm mmm mum femiu'n men-idem 11:12:; . .. . , . 93 '97 93 99 . 130 ”frfl‘! 102 1 . .. - . . - . - rs: . r...) w Home" mm atomic number symbol ml»! :- ILLUMI'BW mm' m. - ‘lamhanoids Page 14/14 ...
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