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9_2536_06_T2a_soln - Test 2a Name “w“ 0 Chem 2536...

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Unformatted text preview: Test 2a Name “w“ 0 Chem 2536 Pledge: I have neither given nor received information on this test” Spring 2006 Table of Some Reagents I) KMnO4 2) H3O+ 1) Zn(Hg), HCI 2) ”OH SOClz MnOz NBS, A, ROOR 1) Provide the mechanism and product for the acyl substitution shown below“ Label the electrophile, nucleophile, and leaving group. (8 pt) 0 o 70 O I n (‘H n + “.9. CH _-C -0 _¢~cu~5 154—51 N ‘ 40 ..—- U' 14 /&’\\_x J? 0"“ D 22 fl, u ’ b / UgAJWG Guam)? H ,0 l O O H CH I‘ oar 3 \l/ 9%“ \A 0 1\ Mac wells 2) Rank the following carbonyl carbons from most reactive (1) to least reactive (3) towards a nucleophile. (6 pts) >‘0 0\ CH3 OYNH H30 >—‘CH3 0H3 :: Ci _..,_Z______ i m3 3) Propose a mechanism to Show the formation of the following product from the given reagents. (8 pt) E? O O O-C~—CH C7: u + + , + “ <—~—— CH éCH 3 CH3®~OCH3 CH3COCH3 3I 3 OWCH3 o o (343 «c, ”all 3 D 3 “s X: (Log _., ‘1 “a ” fl ”3 0 12/1, CH3 _ (1—,; _...—-D “" (ll—(3 o i __(;——(:u Cu? 3 (343“ O 4) Give the following compounds IUPAC names (4 pts ea): an O 0 li I; H30‘C”‘O“C—CH2"CH3 ETHA Ofe— PV’O AND“. ANHVDEIDE— b. O H 001:: ENZWL cu LJIZ 4 pt: 5) Match the term with one correct structure. There may be more than one correct structure and structures may be used more than once or not at all. (2 pts each) E saturated fatty acid 0 gm butylethanoate G. iom/‘N “fl", ethanemide 0 2m cthanoic acid H. /\J1\0/-\ I)... caffeine 0 For i couid be used to make soap 1. /U\CI I: Kevlar (polyamide) J. A. i ”30 CH3 OHHSC CH3 NHZ H30 CH3 0 B. .AJKN/‘x CH3 ! H O c, K H c 91-13 ' 3 x N o N > A / . NHW 0 N’ N -MNH " 3 CH3 L O o D II 0 0 A {03,0 H} OH 13. O O HO N/CH?‘ CH2)” 2 \ H30 OH 0 \ 6) Use the following FTIR and 1H NMR from a compound with the formula 0611320211) determine its structure. (IR. and NMR charts are at the back of the test) (20 pts) 3. Label the stretches in the IR s-eetrum. CFO —-—--——--—> | 2983 l 1588 Wavenumbers (cm ' ) 4. B s 2. a . triplet singiet tripiet (3. Give the structure of the compound and using a, b, c, d, and e shown on the NMR, identify which H’s lead to each signalt 7) Give the major organic product for each of the following reactions. Give the substitution product unless otherwise noted“ (6 pts ea) an _, O 0 u HOH IL , CICCH3 H0 a, 943 b O O CH; 1 ""“x /LL N «~04; o + 2eq HIEICH3 «ms- K¢1 .._ “$4 CH3 {/0 i4«—N"'C“3 0 (Show both eq) 0 ‘CH ” 3 C. A 8 NH2 0 {3%} K ,oH —————————-----> ’" ~————~—I- l \ NaNO ,HCl. 00 ‘~ H o / 2 g 2 d. O O H H C‘OH 5’21 GA 0 + roomy-+20143 / 4» . :4 Swan 29% 7) Show reagents and intermediates to prepare the following compounds“ (6 pts each) a. o 9% NH H30~CH2-CH—NH2 T No} 1314 o ' 1C“ 3 + , ~cu + LN; “0H N3N~CH 6‘12. 3 A +~ a H ( 14:0 H C E 0 H \d ’ k I \ wwfflggwwm ' * -cH”CH~CH KIT 7 b N \ 2 0 CH; 9% CH3CHCOCH3 Cu) 9% (H) CCHCH3 if My? x \0 ,NC‘; 3 C l4 O i 3 Cl g CI CM 3 ~—- .. C‘HD H — m l cwsau u ‘mm—«a cur.o+»cec\ 0 $ H ' 0 Extra Credit (3 pt) What mammal has a heart the size of a small car (and a prehensile penis)? E L0 E: W H ALE. ...
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