key exam 1 - Exam 1 1 A exaoHy probtcm L49 Name AL“—...

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Unformatted text preview: Exam 1 1. A. exaoHy probtcm L49) 9/19/13 Name AL“— Provide the IUPAC name for each of the following compounds (25 pt). 3L| CHa—CHCHZCH3 (CH3)3C—CH—CH2CH2CH3 II C C(CH3)3 CHchz—CHCHCH3 CH(CH3)2 U 1 W t BW’V'IL'M/ W X M 6 ’ eye/cpom‘y/— 3 7,75%?! , 4'1”” y/ocm 3 , 3«M~2,2,4,S~WWWW 33.2w" V’isaffonL 3'MM00M C 2. Draw a Lewis structure for each of the following. Show all non-bonding electrons. Show any octet resonance structures. Place appropriate formal charges on atoms. (30 points) [4. fie” l—u PWWW u—cl 9 9—6.: ea .. e .. __ l _... s «02 l l4 “ :1) 3. Draw five structural isomers for the compound CaHu. If you draw the same compound twice you will not receive credit for it. (10 points) M ML 4. W .. 7%” m 4. Draw all possible all-octet resonance structures for the following. (10 points) H- 9» l4 H ‘1 (4 l —N- C y (L \C—é—Eic:N. a. [CHZCHCHCNI ;¢=£“E”C=’ ‘ é A H (ii i, H l" H” . :1 P.‘ . ’H \d’ b- ”L, ,H "a; “In 4“ NH | // §iéfiwr 2 i2; 1:3 <ér—57 [iii:l\ <E-€9 L§:::L>6. 2‘31; 6 / 6’0“: .55”: a ‘04} at” monoclal/ odd" color ch,“ 6 OCH3 5. a. b. C. Using curved arrow notation, show the most likely acid-base reaction for each of the following pairs. Indicate whether the equilibrium favors Reactants, Products, or Neither. (21 points) KOCH3 + HCOOH . ‘ {(9 NaN(CH3)2 + CH3OCH3 a9 :N’CH; [La-cavo— CH3 9“” :N -(H a—é—o—q-i l i ..~,. I 3 , .3 Ava/s reach/M’s CH3COOH + Br' C3 . t: “6 K“ a 6‘6 H ‘3 c“ ._C -9...“<./‘\;13V: -—9 Ci+3,.C ., , . Y' «if, wflw q’V 6. Draw a picture of the following compound showing the geometry (appropriate positioning of all atoms in space). Indicate the orbitals making up the sigma framework for each bond. Show the positioning of the pi bonds in space. (15 points) CH3NCNCH3 CRT-l}? : c; : 10-»6 H1, 7. Place the following acids in order of acid strength. CH30CH3' [CH30H2]’, CH30H, CH3(CO)CH3 (12 pt) strongest acid 9 0 H3- 0 — ‘C “H ICHSOHg. 5+ H H.4- cw’éia “+ Cl 0 CH 9. a 6 'C'é-4 H ,0, c% i weakest acid 8. Place the following in order from weakest base to strongest base: [NH(C0)CH3]', [CH2(CO)CH3]', [CH3]; [CH2CHCH21- (12 Pt) strongest base 8 all {4 O i ll CRLCHCH? (Jr’gwc'chs 6 6 e H H Ell—lac.» (1939 ‘k l @x" c::C-— C {4/ \l4 weakestbase 9. Indicate the dipole moment in each of the following compounds. If there is no dipole, write "zero dipole.” ( 15 pt) a. CCI4 2,9413 d1(0(? ...
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