Midterm 3 Key

Midterm 3 Key - page 1 Chemistry C3443 Fall 2004 Midterm #3...

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Unformatted text preview: page 1 Chemistry C3443 Fall 2004 Midterm #3 75 minutes November 15, 2004 Instructions: (1) For some questions, you have a choice of which problem(s) to answer. For these, cross out (X) answers you do not want counted. (2) Notice that for each question, we have suggested how much time you spend on that question and indicated how many points it is worth. We suggest that you first go through the entire exam and answer the questions that are easier for you and then go back to the questions that are harder for you. (3) Put your name at the top of each page. (4) Unless indicated otherwise, all structures should be skeletal (line) drawings. The exam contains 9 pages (including this face page). The total number of points is 100. I. II. III. IV. 1. 2. 3. 4. V. TOTAL: / 100 Name: I. ‘ Mam m Lama v Explain using resonance structures and free energy diagrams Why N,N—dimethylaniline A page 2 is more acidic than N,N,N—trimethy1amine B. What are the approximate pKas (units of 5) of A and B? (10 minutes, 20 points total) \E/ G) I NCB /H\ A B p Y EL 1 " 9’ ‘v \0 \ he} « it 1 ~ \ / + 4' Ix’ 3 ~‘ f w 5 \C T x 4 y ‘‘‘‘ N 7 w \ “ff :2 5 , JEN g 3k ; I “‘ -;~ '—»~ ’ f) ,r- ~- 6 \7 . . , '- L L f HIV {pi/\yw‘uifi f’hle HM; Mud H» M3 aw truism-M? ii» 5 0f ‘ “3 iIQ§ _.H‘+ .\ ,x/ N\ swimwimwzy [w a\i\ \ H i Jr'vu . ‘ ‘ l' A‘ I i " i M mu ‘v"\0~v-L€ 5mm {\W Madam \f i“: “Win? Cim xii/L14 tithe WAQ , . A it i T 3mg \ Ab a I At ,, r. i ‘ * mu Wm“ WM. 4 w 4 t W Name: {\VRCJWV \Cfl ivCiVWC;Ki/B ‘“ page 4 111. Using BOTH a line drawing and a Newman Projection, draw the most Stable conformation of (2R,3S)—2,3—dichloro pentane. (5 minutes, 10 points) HI \Vx\ It“ f \ G. Name: pa 0e 5 IV. For each of the reactions shown below, fill in the box with the appropriate reagent, major product or starting material. If NO REACTION occurs, write “NR”. Choose 3 0f the 4 problems. (15 minutes, 30 points total) 1. ><OH A 2. 1. BH3, THF M 2. H202, NaOH 3. MeONa / MeOH 4. CO —._——> THFzHZO Name: \l‘LClUVlEl lib/Mng page 6 V. FMOC is used as the a—amino protecting group in solid—phase peptide synthesis. Propose a reasonable mechanism for the FMOC deprotection reaction, shown below. In addition, explain why such a mild base as piperidine is sufficient for this deprotection reaction. (10 minutes, 20 points) solid ? )1 O 0 support —07]/\N O . __H_.> O H O DMF solid . support _0 NHZ + C02 + o O )6 : -. K, _ 1 ‘ 5 $5 Fee :Jm fl \~-< A? ‘ >1, * “\5‘ i" ~-~ ------------ w m Mb I A .2 / V /( 3“ a . ’J . “:4 i l- _l ‘1‘ \A \\, 57., i IIIIIIIIIIII Ms M/ “Mt; i U!“ W y, l) H is 1' 0 / ." "r L¢l .31.;- amdm, \l 5 CL'V‘JWSM‘E“ half: ink/mt} *{V‘Qhfifl \5 d W) 3m (m moth-Ci “mil " Cmu> 0‘ \w\o\ page is met-35mg . I. \omc \s VANS WSWde slum.th B; “(L ‘/ wwww WW5 (.1 (a etc.) also OWJZV WW3 I. f Kelflflc’ pl (70-; i8 "vevb “'lavu‘w‘xble, > Name: page 9 Insert Pen'odic Table Here ...
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Midterm 3 Key - page 1 Chemistry C3443 Fall 2004 Midterm #3...

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