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3165354392 - | CHEMISTRY 221 seen EXAM 3 Ma rah 25 2003 Be...

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Unformatted text preview: | CHEMISTRY 221: seen EXAM 3 Ma rah 25; 2003' Be sure te- read each question Carefully. This test muat'he taken in gen. Teats taken in pencil will net be graded. Partial credit will beaaaigned where apprapriate. To receive '3 fiJll credit yuan must answer each questidn completely. Relay: and gnarl lucid! 2. 1. {6' {its} Provide the apprapriat'e IUI'AC a'r eammal name for the fallaWing compounds: 3. I 4. 3rmlorDF1—-e+iq —€rr~wil- l-H— age Ml Ear ' H-aaemp Fan-Ian 5" -— 6. Beam: i F5 (gear-ma; $-15— ache-ladle] q. n [or acmequ-dwqj a E. ' I gr II E -E+l-. ln-Eamu'es -—'L '* .Ml'L F-HF-L'Lf '11,. || 3 1a. a if mphfi'l‘frfll] 1 |_ 2. {4 [its] Draw the proper structure far-eath af- thefallawing eamp‘aund names: Tntal: ‘I ,E-diathnxy-fi anelh exy benze ne see-hum isebuiy'l sulfide 3. {3 pts} Rank the following sets of compounds in order of'their increasing reactivity toward nucleophilie aromatic-substitution. Order this set from least [1) to most (:1) reactive. Write the appropriate numbers it: the spaces prositted: i @“fiéé IQE} 4. (8 pts] Proride the appropriate starting materials for each reaction type tistéd below that will generate the ether product shown below in the best overall yield (ie. minimized product mixtures}: fit}? Wiiliamson Ether Synthesis: Alkoxymercuration: —‘§|/\NY#\ II-J 5. (9 {its} {a} Rank the acidity,r cffltc fallcwing acids from law [1} to mcat {11) acidic. Write flic ccrrccpcnding number for each compound in thc bcxcs prcfidcd below: H OH OH 6 (1]) Indicate your rcaacningliarr drawing thc conjugatc basa cfthc strccgg' st acic'i1 showin- all rcs'cnancc farm . Ccniugatc Bacc- c_f th_a Strangest Acid: 6. (1|) pts} Prmride the major product for the reactipn 511mm helaw. Draw the majnr product in the appropriate box and than, using curved arraw formalism, Show the step- wise mechanism fur this reacfiun. DH 2. NaCICHzCl-ia T. {5 pts} Using reagents from the table shown, suggest a synthesis for the fullawing' transformation. Show all reagenfljs} and intermediates: Bangui; 3. area. H313” r. H2. Pd k- CH3CH2MgBr I b. Mg. Etgfl g. PBr3 |. heat C. H200 I'r. FCC. GHECIE m. H301.- d. EH3, THF I {CF3CDfl2I’I'g [1+ NEH e. TMS-CL j. NaBHg 0. H202. GH- NIGWGHfla D x" DH :1) 3. [5 p15} Using reagents frum the table shown, suggeat a synthesis for the fallowing transfurmation. Show all reagentfi} and intErmEfliate's: may; 3.1;":ng H311")? 1‘. H2. Pd k. CH3CH2MgBr h. Mg. EtQQ g- PBr3 L heat a. HECO h. PCC.-CH2{}I2 m. H3? :1. 3H3. THF i. {CFafli‘szleg n. NaH '9. mam, ;. Halal-L1 0. H202. DH- momma}; DH - H0 H3 9!. (5 pts) Using reagents tram the table shuwn, suggest a synthesis fur the fipllnwing transfsrmatinn. Shaw 'all reagenfls} andjntsrmsfliatias: mm; a. Crag. H30+ 15 H2. Psi k. CHacHgiulgBr b. Mg. Etgf} 9. PH} 1; heat c. H2110 h. Pes'CHaslz m. Ham :1. 3H3. THF i. {BfidflflgHQ n. NaH 3. TMS-CI. j. NaBHJl1 0. H202. DH~ mums-7mg OH OH G + firm :3.- 0 ll]. {23 pits} Complete the following reaetiu schemes by providing the appropriate start materiefls], reagents{s) er-all possible predue.t($): 3 § 1.be0HH20.amec.1?eauj OH 211,131+ | OCH-gmlhj L- 1} ”30" ‘ 1. p—Teiefl. Wfidinei Z CHEF-[2 CINE 1. exe'eefi GHact-bhflgfir + MED H 2 H3? 11. (22 pts) [Sample-ti; thefnllawing reaction Schema by pruviding the appropriate starting materiafls), reagentfls) or maimj- pmductfi). Be sure to indicate pruper I stereochemistrywhére-necfissmw: ' 'fi 1. H2“ — [:“NHZ —h—- 3“ 2. H20. NaBH 5 H 9 ———J HBF 1- H3113!+ ————p... HBIEHH [hail-KM. I) H.391" —I- Nl‘hU'H. Hzfi. EfDH W 1. mum. H29. MIDI-l '2. Hair HJnt: 3W Readim 11 ...
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