Midterm2Key

Midterm2Key - Chemistry ns C Fall 10116 Second Midterm Wed....

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Unformatted text preview: Chemistry ns C Fall 10116 Second Midterm Wed. November 15, 2110-5 Instructor: Lievens This exam contains seven (7) pages and six (I5) problems. Please make sure that grew cop}r contains all seven pages. If there is a problem, please tell the exam I sdministra‘lur prior to beginning. Please answer all quesfinns. Remember then Uri-Ilene Code ofAeedemic Conduct applies to this. exam and all Elmer graded work In thls class. Name: Last First Ml Student ID. # "RAJ Lab Section: l. {4:} pts}. Draw lbs struclun: 01' Ihc :xpcclcd organic productis] fanned in the Following reacliuns. Assumc all rcagtnls listed are present in excess unless n'lhcm'isc noted. If no reaction occurs, state ‘Nu Reactinn'. 1} CHEL mi” M 2m 0 H 0 LEE [ill g2 I 2 HSC / CH3 NaNOZ. HCI a) “W” /\ l" f H H20, 0°C lybu CI. Cl. hv, CI2 (2 eq] 6 C) ——" 0,) 0' JV”?— NOE [Ml—laj {.5 Nb:— D} —— L” M N02 0; 0 D 0 NaDCHB {cat} E) 00Ha firms HOCHS l D + 2:! 1 UL H3 1. Continued. Draw the stmcture [If the expected organic pmducqu) Fem-led in thc following reactions. AESumc all reagents |is1ed are present in excess unless othenvise noted. If no reaction occurs. stale ‘Nu Rcaction‘. “\L 0 a F} o 1) NHIECHallz. CH2=O1 Hcr G} \6 2] Nch03. H20 0 11 NaOCHa, HUCHS H]. Esq \I/lLDCHS N R 21H30+.H2ID Cr 0 1}K2003 N . EjBrGHECHECHglflHQCHa C VII“ + NH ' N I} 3; [~1ngle2 V” “a: 0 (3H I. '3' 1}KDH,H20, A h '*{ “1) © 340%,150 atrn “ail 2} HSD”, H20 2. {10 1115.]. Show detailed reaction mechanisms for the following reaction. Include the structure :1me expected products. NH; 1) Nari-DE, HCI, 0°C 2 0 G! l u H?! G .“‘ a fix 0 “avg-MIC +H'C! 3:?N1U + IRE—“:3 Hafififio H t - 1? CW Q) All H g 4- N30 /-"‘"r' “3%.: f -_ rflc‘fl Zr. I If n d; Ll J C, -" HIL’UPFl wt Ill—NEH fr" H”ij [3 m” Calm r‘“ ——-3 A # «5- l N ( .H‘ 3 Um; 3. (14 p15.) Show how you would carry out the following synthesis. Include lhc reagents ymt would mad for each step and the Structure of the immediate products fonncd in each step. 3??“ '1‘) Err/v 3.91? 11 ‘tt c: M, HLD Qt (LG x“ “0MB ___._—_-—-7 H 4. {8 p15}. Rank Ihe following compounds in decreasing order ufacidity. DH “Hz OH CH: Eight N02 0” DH “02 CHaCHNH GHgfiHzNHz ND, ND: A E C D E F G H E>H>BVF>D7k>g>Q Highly Acidic Moderately Acidic Poorly Acidic 5, [8 pts.) Provide the systematic Mints or structure of each fifth: Foilowing compounds. DH . % H'Eimifio-ghramc -Pligncl N Br NHL F 1 Bi N,Mdimethyl-2-aminn-Evphenyi-pantanolc acid H 0 _/ fifvfiflk w QJ / I '\ “3": “:5 J I-cmr i:th C] 04- «L _- will [Ibr‘fflchyf‘f'al‘bu'hinflminfl D D} - HENWO© S; nfi‘eh‘fijl - (a ' Fifi-EVIL??? ' ht‘KQnQ m: {Lg «E. [20 13:5,} The unknown: compound A {CHI-[[103N) gives the following proton and carbon NMR spasm. Significant 1R peakfl were aim observed 200 151‘.) [00 51] ER: 335G [broad]. 3-0111}, 29541, 1810, 1793. and fiflgfl'PTh-IL What is compound A? *c g Gil/3"“ DEE f 1111' Esp-Pr; gnylamw. (WT Iwwml alum: w . 1T1 t‘l‘k Ti‘h'av' 3?”? w‘nuflg Com Fav'rlci KEPT 1‘ may. aim (i 3‘91— Av’l lhfflif'iflig; Biff N 'H 1131' T ...
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Midterm2Key - Chemistry ns C Fall 10116 Second Midterm Wed....

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