Exam3 - WM ' PRINT NAME 5 1X. (12 points) Using the...

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Unformatted text preview: WM ' PRINT NAME 5 1X. (12 points) Using the chemical shift tables (page 1), draw the structure in the box provided of the compound Whose N1V£R spectra are shown. The molecular formula of the compound is C5H100. Partial credit. Will be given for correct structural fragments. Structural fragments outside the box will not be graded. Note that the other stereoisomer of your compound has .1 A3 = 15.1 Hz. JAB=10.9Hz C D ~E q d tri 2H 3H 3H A B d,q d 1H 1H ’1 I I r— “r— T" T”— l ‘1’" 7 6 5 4 3 Z l 0 PPM 1 2 3 4 5 6 -1——r' “r— r—r' [—1 [—r“ 1 l ‘1 220 200 1 80 1 60 140 ’I 20 ’1 DO 80 60 40 20 0 PPM 307/315 EXAM III DRAFT FALL 2010 5 PigN—T NANIE IY. (12 points) Using the chemical shift tables (page 1), draw the structure in the box provided of the compound Whose NMR spectra are shown. The molecular formula of the compound is 061-1100. Partial credit Willlbe given for correct structural fragments. Structural fragments outside the box will not be graded. Note that the other stereoisomer of your compound has J gaff 10.9 Hz. JD‘E’; HZ C B q d tn 2H 3H ‘ 3H E D d,q d 1H 1H 220 200 ’l 80 'l 60 ’l 40 ’l 20 ’l 00 80 60 40 20 0 PPM 307/315 EXAM III DRAFT FALL 2010 6 ~ - ‘ PRINT NAME 2X. (12 points) Part A. Using your general knowledge of IR spectroscopy and the table of ' Vibrational frequencies provided (page 2), unscramble the following. You have four IR spectra with characteristic hands, as indicated, and five possible structures, as shown below. Spectrum a) 3300 cm'lg spectrum b) 1630, 1750, 3030 c1114; spectrum 0) 1630, 3040, 3310 enflg spectrum d) 1738 cm'l. ‘ 353“??? fl , 5 KC EH(CH3>3 4 5 __H Spectrum abelongs to 41: Spectrum b_belongs to A ‘ 3300M" OH 57330004“ 9:29 };_I lé§00~0"C—=~'C ' 00w? ' 7'“ 7‘; I *LSpecfiurncbelongs to _‘_S___ Spectrum dbelofings to .3) + Z, amow‘ OH H t738w? C30 30in) w" "rec—H \é30 cm‘ ==C Part B. Determine the degrees of unsaturation of the following compounds. + l C5H4Cl402 ‘ - has 3 degrees of unsaturation [9,0,9 (A C5H6ClgN2 has O V degrees of unsaturation C6H4C14N2 has degrees of unsaturation C5C11202 has j... degrees of unsaturation C6H4C16 has degrees of unsaturation 307/315 EXAM III DRAFT . FALL2010 7 I"; NAME 2Y. (12 points) Part A Using your general knowledge of IR spectroscopy and the table of vibrational frequencies provided (page 2), unscramble the following. You have four IR spectra with characteristic bands, as indicated, and five possible structures, as shown below. Spectrum 21) 1738 cm—1. spectrum b) 1630, 3040, 3310 cm’l; spectrum c) 3300 cm’lg spectrum (1) 1630, 1750, 3030 enfl; OH O / , . O 1 2 3 CH3 (5 d , > OH . > {Ema-13)3 4 5 - .3 . r 5 .+ L ‘ Spectrum a belongs to ______v__ ‘ Spectrum b belongs to p ,. t ____ +11738wn” c=o “WOWZ! Qtfl 3 '630W “‘5- _ _ 301m cw “C— H Spectrum c belongs to “3; Spectrum (1 belongs to L "lL Z/ 2;] 3300M“ O‘H I'lb’tflw" C20 3t650ue;‘c:c' - 3030mm“ :cwH Part B. Determine the degrees of unsaturation of the following compounds. fl, I C5H4Cl4N2 has degrees of unsaturation Lax/k C5H4Cl402 ' has , 5 degrees of unsaturation I C6H4016 has ' degrees of unsaturation C5C11202 has degrees of unsaturation C5H5C18N2 I has 0 degrees ofunsaturation 307/315 EXAM III DRAFT FALL 2010 I 8 3X. . (12 points) 307/315 EXAM III DRAFT FALL 2010 6 PRINT NAME In the following reactions, fill in the missing component whether it is reactant, reagents or product. In case of stereoisomeric products, write out only one of the possible stereoisomers CHC13 ——-——.————-—-> KOH, H20 3Y. (12 points) ‘ L _ ' Q/O/ ' / . PRINT NAME In the following reactions, fill in the missing component Whether it is reactant, reagents or product. In case of stereoisomeric products, write out only one of the possible stereoisomers * HCl 1 --—--——--—--——-—-> 307/315 EXAM III DRAFT FALL 2010 10 ; PRJNT NAME 4X. (14 points) In the following reactions, fill in the missing component whether it is reactant, reagents or products. In case of stereoisomeric product, write out only one of the possible stereoisomers. 6:7— )z 51/ H2S04 / H20 HgSO4 /\/u\/ M 1- BIZ z) (6“? 2. pp) 14143,) IONS’UR) 307/315 EXAM HIDRAFr FALL 2010 ll P T NAME (14 points) In the following reactions, fill in the missing component whether it is reactant, reagent r or product. In case of stereoisomen'c product, only write out only one of the possible stereoisomers. ' 4Y. z. mm for! ——————————-————-——-————> H2804 / H20 307/315 EXAM III DRAFT FALL 2010 12 J ‘ tr: ~ P TNAME 5X. (12 points) A. Write out the complete mechanism for the reaction shown below. Be sure to include all lone pairs and charges. Use appropriate curved arrows to indicate movement of electrons. Show stereochemistry and regiochemistry. - B. On the axes provided, sketch the reaction coordinate diagram for the reaction described in part A. ’ Lack MAL ,Mrw) r/m Reaction Coordinate . 307/315 EXAM III DRAFT FALLZOIO 13 3 PRINT NAME SY. (12 points) A. Write out the complete mechanism for the reaction shown below. Be sure to ' include all lone pairs and charges. Use appropriate curved arrows to indicate movement of electrons. Show stereochemistry and regiochemistry. B. On the axes provided, sketch the reaction coordinate diagram for the reaction described in part A. ' Reaction Coordinate 307/315 EXAM III DRAFT FALL 2010 . 14 \2 P T NAME 6X (10 points) A. Write correct IUPAC names for the compounds shown. Be sure to include all necessary stereochemical descriptors 1 x “7 '\ [ax +rM) +1 4 x’4‘ } -Q~oc75~—é- was ” W ‘ 1‘,ch *—Z—EH~6’Y“£ (,4 WSW . r. L, / wrong 7w; v ‘3 "L 72x95) «gem: '(1/2, ~2-cchamzx ‘ Mac, TM 71-- A“ 0410 H z #2» We ((71 41-0!) . B. Draw line structures of the compounds whose names are given. 307/315 EXAM III DRAFT FALL 2010 15 OWL/xvi Wm} : (39,6 PRINTNAME 6Y. (10 points) A. ' correct MAC names for e compoun s s own. e ur 0 mo “117" (f/ Com/05 ujgfistogfiéjié 6 MM r 3 (, / W 6 W) (E)—2,4,5-trimethy1~3-hexene W”) ' ,2. / ‘ propargyl alcohol B. Write correct IUPAC names for the compounds shown. Be sure to include all necessary stereochemical descriptors ‘ [avirazws‘ ‘ (/ wig,» 4,41 IZTN w —z— c YCLGHEXiNOL (Ithés) * (9"7’37’9YLCYCLOHEK'1'EHQL SW ,I v 09 307/315 EXAM III DRAFT FALL 2010 16 PéfiT NAME 7X. (12 points) Using any and as many one or two carbon compounds as you Wish and any inorganic reagents, devise a synthetic sequence leading to the formation of (Z)-pent—3—en—2-ol. Be sure to show each reagent above the arrow. Designate each product generated in the sequence by a Roman numeral. When these products are employed in the sequence they can be indicated by their Roman numerals. OH V I0"! “Hm/“"3"” 1 rs CB ""- szfl—CEC'H M H- C56; am J; “‘73 I + Wig—73:2 -——--—-~——> H'CECj-CH3 Z? NflUHz) Nikita-{M Q ,Yl II , ~ ~ macs—:cvmj Tj . O OH 3 _ ' .—-—' 4” /“\M. [75/70 au3/%*CIEC"¢H3 J} OH 4 4’?» L! ‘ LINDLAIILS CF/3/;S\CH:CH -———-———————————————> 307/315 EXAM III DRAFT FALLZOIO 17 % 7Y. (12 points) Using any and as many one or two carbon compounds as you wish and any inorganic reagents, devise a synthetic sequence leading to the formation of the compound shown, (Z)-heX—3-en—2-ol. Be sure to show each reagent above the arrow. Designate each product generated in the sequence by a Roman numeral. When these products are employed in the sequence they can be indicated by their Roman numerals. OH / ——————————-——l-—————>- 63., 509 mm, mum fled-:4“ch * Adana—m 1, WM ' ' H~CEC~CHI~CHJI +5 j + {HJ'CHI’EiZ . e, Am NHL, NH} peg) \ #7; [l MpnjczC'Cmtcté’sfl Q - I ' ’ @942: E 5“ . h I fl . 1 +3 [I] 1:. H/cumfi [.5 64431» ewe—.6; pug-(H3 OH- I 'f‘7/ 77 Ha " NH" \ ___fi x04? 3 / I éthLnk's [awe WA W 307/315 EXAM III DRAFT FALL 2010 18 1697 . . PRINT NAME 1. Arrangethe following alkenes in the correct order of increasing stability, starting with the least stable One. l<2<3<4<5 5<4<3<2<1 5<1<2<3<4 A B c; 5<2<1<3<_4 E. 5<2<3<4<1 , 2- . Arrange the following compounds in the correct order of increasing number of 13C NMR signals, starting with the compound that has the fewest signals. “\u“ 5<2<4<l<3 B C D 4<5<2<'1<3 E 4<2<5€3<1 307/315 EXAM III DRAW FALL 2010 3 V ngr NAME 3. Rank the following compounds in order of increasing pKA (IOWest first, highest last). Y \/\OH HZN-fH H ‘ . y . H 1 2 3 4 A 3, 4, 5, 1, 2 ,. B. 2, 4, 3, '1, 5 ’ C. 5, 4, 3, l, 2 @ 3, 5, 4, 1, 2 E. 4, 1, 2, 3, 5 4. ‘Which one of the following reactions produces a meso compound? ' CH3 A. g; H, , ‘ . ' Pt ‘ H30 CH3 , CH3 ' . H2 -—-——-——-—)~' Pt H3C. CH3 5. What color is your exam? A. White B. Green C. Blue D. Yellow 307/315 EXAM III DRAFF FALL 2010 CH3 C. Q CH3 H2 . .....__, Pd H30 CH3 E. Brg . _________> 0014 I Brz ____..._._>. CCI4' ...
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Exam3 - WM ' PRINT NAME 5 1X. (12 points) Using the...

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