chem-3332TestIB_Key - A. Nomenclature (3 points each; 12...

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Unformatted text preview: A. Nomenclature (3 points each; 12 points total) Please provide an acceptable name for each of the following compounds, noting stereochemistry where appropriate. O QCHgCHg :33 CH3 2. ~ - -‘ I CHECHQCI l CHSCHszCHgoH 3. 4. CH3 ‘ * . CH3CECCHCH20H if " BEFACTS: Total Points = 15, 3 points each 1. Rank the following compounds in order of increasing acidity. (i=least,‘ 3=most) CHgCHQCHs ‘ NHs CHBCEC-H VE] ' E t 2. Flank the following compounds in order of increasing boiling point. (1:IOW€$T, 3=highest) cescE CCH2-OH CHBCHZCH2CHZCH2OH 0\ > if] 3. Flank-the following compounds in order of increasing reactivity in HBO/H30“. (1 =ieast, 3=most) HsC\4>/cll3 CHBCHEOCchHa A E 4. Circle the halide(s) that will produce a terminal alkyne as the major product when treated with KOH at 200 C. Br . _ Br ?r ?F I ' I BrCHz-CH-CHZCHZCHS CHg—CIE—CHECH2CH3 CHs—CH—CH-CH2CH3 Br Br I any“. :. n. f 'r .' L'fin- . . w Cngc—CHgCIHzCl-ia ‘-' '- ‘ “if 5. Circle the compound(s_); that will produce a Grignard reagent in good yield when treated with Mg in dry ether. 9* i " fr CHBCHz-CH—CHzBr CHSJC-CHZCH2Br CHs-CH—CHECHENHE x, A” ‘ ../" (-1»... _ 2L ' Tl 0. Reactions: Total Points : 35, 5 points each In the boxes provided, please give the major product, the necessary reagents, or the starting material for each of the following reactions. For multi—step reactions, piace only the product of the final step in the box. intermediate products may be placed below the reaction for partial credit. When relevant, indicate the stereochemistry in the product or “starting material. 1 / I ‘N 1 OH H c . __ 1 CHag:—CHZCHZCHZCI 2' HI (XS) 3 was CH, (1 H flatlny _ A 3. CH30' Na+(xs)/CH OH ac: \® 3 - e > . _ atC’llgcl’eC/rrZCm—cap / ~——7‘) .l O . @ I! 1. NaNH2/t 50°C Br Br 2- t r 0:0 3- CHa-CH—CH—CHs —-————-—-———-—————-—>— a. Haot \CD ‘ . ‘4. Na/NH3 CE— 0(3th OH .I "" L.-13 3 ‘ . l —7-_ I/ / , A/x ‘ / 1. Sia2BH 2. H202/OH' 01+ E - I + r -_ fl 4' CHSCH2C 1CH 3' (CH3)ZCHMgBr 3a 2 CH HSO+ a E 5, H2804meat ah, ah CPrLé “H \63” i?“ (4+3 uth »Q-+ — 9—6443 “5 1. Br /H O OH 2. NégOl-El ‘ (“EH3 W CHSCHE"CH'9'.CH3 Cl Br I . 7. CHBCHgC(CH3)2 2. Hg(OAC)2/H20 3. NaBH4 D. Spectroscopy: (10 poinfs; 5 pts each) 1. The [R and 1H-NMR spectra of a compound with the formula C3H5O are shown below. Please identify this compound and draw its Structure in the box below (5 points). 11 u u u mun" an 13 . ‘ V. . ‘uLI it! LllTil'llJl—ltl? , . '“QJ IN‘N‘NW“ /f~whw\\ ____u n . a. ‘. “kw-u ’2 NEAT "* m - - ‘“"”"‘:_2i and um um am: an and mu 1:.» an 2-: m am an an vu “4:3”.H‘ mu ' un- Tou- m _ ECOLE‘Tzwfl'I; mu 1.--.2 ..3 .. g. a e w 39 .. " m 50 5:0 45 30 in 23 '0 B — ‘ If! 9 3 7 5 5 4 3 2 1 G (I. 2. The IR and IH-WR spectra of :1 compound with the formula. C3H7CIO are shown below‘ Please identify this compOund and draw its structure in the box below (5 points). ‘u-uuufig4yflg u s I u I r a I to II r: I! u “1an1. nag, n-é' «i _ lg“. "if-«Iran Dino {Om ummmma 30o!) iscc ‘3“? Ham mg“... ~_1__,_...3...-._.-_,-f__..._J- -__5 _ __5 _ 5 9 m ‘ g l I L I; . k . . . .. 9“? I T'LIT',’ : ‘3“ 5' ; "‘fft‘i‘:t“' ' ‘“' "1!? 50 .-.-. .... -: .-..i.... 30:1. .1; , : i mi ID ; I] U c an »— a Fatwa/713 E. {\‘Iechanisms: (15 points total: 8 pts plus 7 pts.) 1. PmVidc a Clear meChMESm for the fOHOWing maCtjon. Use. curved fm‘ow notation to indicate "€160U0n flow". Show all intermediates and all formal charges. (8 poms) H o H Br NaOH H \ 2 H20 AWE“? L' ‘ ' a 17 ‘33 Wm "awn-«m.»- m.wm;m_u..x mhfi'fiwwaflhw :racm WK ‘ - 51:61:.u1mmk mm... m 11$ 1 ‘ WHQ-«u‘fiéfiémfm .9 IE, ,er ‘ “nut-mu: 2. Provide a clear mechanism for the following reaction. Use curved arrow notation to indicate "electron flow“. Show all intermediates and all formal charges. (7 points) F. Synthesis: 13 Points Synthesize the molecule below using any of the following reagents: alcohols, alkanes, alkenes, and/or alkynes of two carbons or less, any inorganic reagents, any oxidizing or h—mw reducing agents, and any peroxyacids OH DOE-i3 T l: Mao“ _ , ‘2«- 0145074 WW T lmq/ /> (A?) ~ /@ H Kc —— my org W3 4% I“ mail f: J gm 1 / Cn’ -/ ONE. (2H5 QM 5*, CW) f fgrs if ,9 BVM? 0% (/15 (W: 0,36 49H FOH 7‘ Va Cd ...
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chem-3332TestIB_Key - A. Nomenclature (3 points each; 12...

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