Spring 2004 Test 1b

Spring 2004 Test 1b - flfll'flfi.’ E» d Dr. Wells....

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Unformatted text preview: flfll'flfi.’ E» d Dr. Wells. Spring Emit-4 %W her huff: h'l" Chi. " - I. "':._:'I.'. .. I ..- _ u- - I I“. .' . - . ...'. . . . . .|-.-'I-." -. -I . . .-I - .. I: L score—tipscajt* sot24=l_"l * soowfl we“)! a ggflpfirfir 450 4-2, I ' Whittle“ POM" 5 1a The boiling points of heptanol and octane dil‘l'er by 5!] “C because . Era A. oxygen is heat-'ier than earbon‘h B. octane has a longer parent chain fix [ .3 it x) C. of differences in branching {e E? m “M: PEI ® of hydrogen bonding of b I, K I .. eycn the smallest halogen is Itcat'er than carbon 4. i- '3 JP L an n-Butyl alcohol boils at l l? “C 1a-‘hile t—butyl alcohol boils at 33 “C because A. of the difference in molecular mass (13} of difference in branching Q) C. r—hutyi alcohol is actually an ether D. o l— hydrogen bonding E. oxygen is heavier than carbon 3-:- lIydration olialhertes 1a'ith aqueous sulfuric acid to make alcohols is often useful. but can he a major drawback. :1. oxidation to the carboxylic acid B. formation o F ltetones Q C. H's-trans isomerization ofthe alltene I}. formation of aldehyde hydrates I . skeletal rcatattgetttcttt {a l-lydroboration followed by protonolysis of cyclohexcne is the same as ofcyclohexene. Q\ ® hydrogenation B. hydration C. hydrohalogenation D . inrn—hydrcxylation F1. mitt—hydrosylation Se Sull'onatcs {for/3311ple 1rifylfltt3 and tnesylate] are good [eating groups because of w at. their posi we charge the inductive effect @ resonance stabilization @ two of the above 6a in an acid catalyzed ring opening of an epoxide water attacks :3. either eposidc carbon with SHE/ti probability 6!) the roost substituted eposide carbon g C. the least substituted epoxitle carbon D. itnpossiblc to determine because the products are aehiral E. none of these 7|: LifitlHq is basically a supplier oi" _ when it reacts with earhoxylic acids. $9 a. H—il ‘ a. H—Il c. n “ n. H- @n: ' 8n Fytidinittni Chloro Cltrontate is used _ — - til LI.- ® so that 1a-‘ater may he excluded {‘1' B. so that methylene chloride [dichloromethane‘j may be excluded H all _ C. to convert aldehydes to eathoxylic acids {JUL ‘3‘ 1- ‘l'h D. to convert ketones to cathosylie acids // E. to reduce esters to alcohols 9n Reduction of aldehydes with sodium borohydiide in water involves _ . , , Hl' ‘ EH A. proton addition to an alltoside tr” 1“: la l'fi 'fil' B. hydride attack on partial carhocation v” w E. halide attack on carbonyl carbon 1:. {121) two of these / F. H E. all ot'tltesc 10:- How does the chromie aeid confirm the presence of an aldehyde?1 GD Orange Chromite acid solution turns lilac-green. w B. Brown CID; precipitate forms. ,c. C. Noxious and pungent SD; gas forms. :1“ 1}. two of these R E. all oftliese 3g 11:: The best atone for eootpeand below is _ —. @ i‘lehft‘iFl'lfl-T-Cl'llflt’U-S—Elhyl-{t'l'ltlflt‘t‘JI—li—tflfliflnfll / B. l—hromo—EreltloroA—etliy|r3~tluoro—o—octanol C. 5{3-erIt]fl-2—fll1lt}1'{3-i'l'ltlut't]J-B-l'lflptfll'lfil D. 5—{ I -hratno—3—cli | oto-3~tlaoro}—3—heptanol E. 3-{ I ah tome-2 -chlo1'o-3 —ll noi'o }-5-heptano| 19s 1ii'y'hich one el’tiie lollowiitp molecules is 4untetliyl—1—ltexano1‘? OH OH DH 13:: l-[ow can spectroscopy cool": 9 A. l. M U 'l' rm the presence oFan aldehyde? L. at: sharp peak near woo unri/ M: at.- broad peat.- near ssoo em 1e. N: 'I-l NMR: triplet near I ppntfi D: 'H NMR: singlet near ‘3' ppm 1.! S: “C NMR: peak near ill ppmji T: 13C NMR: peak near [Fifi ppm V" B. M N S C'. M N U T o. MNDS @LOT 11.: Urignat‘d reagents hohat'c chemically as _ A. eat'bocafions $ carhanions 15¢ In the William synthesl s the asymmetric a base that has a conjugate — — l B. proton donors C. hydride donors __ Cot?) n E. lewis acids L others from two different alcohols which is [1'L1 o'?‘ acid pKa greater than one of the alcohols must be used acid pKa less than one ofthe alcohols must he used all. two Selections for this question. The unstudied have a SIP/l: chance. oafi R. a hasc that has a conjugate There are only G) A...) H RFG H J K; 0 + B L I? 9 ta... :2 I r? f”; ‘3’ 16a The major product l'ront the sequence helow ls _ _ _ _ If} H} ‘—————________h__ ['2 t H 3to" t DH /\/Lk /\/’\ M Br 3"... H. C. Nh’lgfll' L 01-! 1kGD Cunsider the MAJOR pruduct l'rum reactinns of cnmpmmd W bellow fur questinns 1'? — Ell. Llil l-Igfll’lplI-Igfl' —————h- I? [lg-1 _ {HTHl-‘rBI-h .. 'l-‘Hj 18 EL”! f {Ell-lgUg.Dl-l' L C113 \ Kn C: /’ l 1} l-lglD.-"luJ3.!Tl-II" 1-1 H h w [EJNaBI-Ll. OH" “I {1 l 'i'l-IFrBl-lg h- Ell l 1H}! 3ClTJ3E-IJ1L-sell ‘ 2" (f1 3 CH CH] CH;— ‘—C'Ih {Illg—{I—Cllg \_u,,.+:.‘:-I1 l {-1 H IE, J | CH: \ H—C——C—H lI——C———C——OH C20 l l | l / a. H H H H H C. H (TIE; LIH-l C}|J_l,_CH3 Ll'lj—L—UH H ' 1-! l J I . ‘_ ~1__ _{ Hli'J—-C——C—|[ "ill-13* (I: l l l H H u. H H E. 17:- Cmnpuund I? 1.lr'muld nmst likely hr: @- l®| 18L! Compmmd IE u'mlld 111051 lillelj: his 19: Compnund 19 would must likely lTIC P75 Cl 90L: Cumpound lfl mmlLl ITH'JSL likely In: ® Jimmy carried out the resctisn helnw. Earl said “How do yttu [10 one withttut the timer?” t D 0t sf G H“ Ox 3/ s . 1 /C tx ——tI- IL.x C H L'II— Ct-t1 H/ H t)-—— ("I-13 F H 9L E'Urtt-‘srsiun rti‘F ltt H is an estttttpis oi‘_ A. eicumttltiiic :‘Irun'lt-‘tlit: sttttstitttt'ttttt B. ttttcisttttltiiiu smtttttttu sttbstittttiutt {2-} oxidation B a rctittcticttt ago The best sitnisu For reugcttt G is _ A. I}I.ir'*tIH.1 EJHgtJ B. FCC-"FILITIE @NttBi-i.t.-’I.[3EJ D. HgCrfltt’iijU 1“? . C, “MEL”. mat-Jih“. Jimmy‘s hack in the lab. His timid}- Ear] said ‘* E. i'-'t1Ci3.t‘H;D 'l‘ttp Jimmy. t'nu‘rc the king.“ I t—-U ,0 l tit I,” :t'; C; -—'l- Qt" g: H H \7.J—— {‘J t t i i— 0/ tJ—— CH3 H I 93:: Cottt-‘ersitttt ttFH to .I is :m cxmttpic ttf' ft. EIDClrflphiHL‘ atrttttttttit: substitution B. ttttsienphiiic st'nttttttit: substitution _ osidtttittn DI. t'ctl uctitttt 911! THE best choice tltr t'sttgettt l is _ _#~ .41.. lleiJ'tiHilngi.) B. i"'|f‘CT.-"t_.'i'i3{'_'lg C. NflBHtt’i'IgU @lhflflfllgfl E. FEChITIgt—J 5 #:1wa 9“ © ...
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This note was uploaded on 06/19/2008 for the course CHEM 228 taught by Professor Jung during the Spring '08 term at Campbell University .

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Spring 2004 Test 1b - flfll'flfi.’ E» d Dr. Wells....

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