8aS10Quiz1_key

8aS10Quiz1_key - Name: Last, First (PLEASE PRINT CLEARL X )...

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Unformatted text preview: Name: Last, First (PLEASE PRINT CLEARL X ) CHEMISTRY 8A Spring 2010 h \C}l’\ Q C‘I’ +32, ;1 Quiz/Exam 1 A my. CH April 19,2010 Professor Sheila S. David For students to read at exam time: Closed book and notes. Please read exam carefully. Partial credit may be awarded if you show your work. For students to read after exam is returned: If you have any problems With the grading of a question, return your exam to Dr. David or one of the TAs by April 26 with a note attached indicating which problems should be regraded and a brief explanation. All of the regrades will be done at one time. Tests will not be regraded after April 26. Note, we will not regrade extra credit. ID Check D Student ID Number: Name: Last, First (PLEASE PRINT CLEARLY) 1. (22 pts) Appetizers A) (4 pts) Draw the Lewis structure for nitric acid, HNO3. Show all lone pairs and indicate any formal charges atoms! \\ J . r, 7" . —‘ ,a +:" ’I r‘ ‘ -t 4H .,t 1: t " 4! a W l 'l‘ 1' '2 V, t “I \ _. rt ____ ~ ‘3 ,N -: c. : 71 ~(, »-~ Iu - O; 0‘, H :O-b“ u. 4»——9~O,~I‘r ,Cfi 1- 7 i - g H / I" | " . I . t y - O: :0: _ ; C": i ‘r 0 - ~- ' ' . a r *. t. Chink "~:«'f‘»_:‘v:)\,’\:fi; 5‘4 " t z 7 "W B) (4 pts) Covalent bonds may be polar or nonpolar. What property of the atoms forming a given bond determines this? Provide an example of a compound containing both types of bond (indicate the polar and nonpolar bonds). W" (W{ {nail m {\Qfitf‘dz’k‘K/li y I .‘4?’ I, I. C "L\W V w ( I in b , (Vlmgy '~ 3 , ' OH .1 T T “‘1 ~ m3 511/ 3 9| "t V yum it (PM; my) | p f hp P P — strut turd - 1 p“ C) (4 pts/2 pts ea) What are the formal charges on the indicated nitrogen and oxygen atoms in the molecule shown below? A} (M‘s E) (2 points) which intermolecular force is primarily responsible for the interactions among alkane molecules? vcmcu f Wtkctlg Op MEL/((02 (7? 02A Uh lynch (Lt S pref”; tU'Yt CL; F) (4 pts) Based on the Kekule (Lewis) structure of CHZCHCHCHZ, how would you describe this compound. molecular shape? ’ m“ {0mg / Ct ll 3 P?" C at‘KLID‘fl,&., 9 WW 961‘; their») / r- . 4 ‘ we) W “Le; +Y‘190‘nall fliram::m am“: 96 ch . ' i— \ fl r 5:311“??? (5 “mt” \ j V 54?" Carports rash: 0 t“ I” ' IOU”); he m [0 50‘“ ma pier/M? Name: Last, First (PLEASE PRINT CLEARLY) 2. (3 pts each, 18 total) Finger Food (multiple choice)—-Put answer in the box at the right. 1. Which of the following is not true about methyl anion (-tCH3)? A) The molecular shape is trigonal pyramidal B) There is a lone pair in an sp3 orbital D C) It is a polar molecule D) The carbon is sp2 hybridized E) The C-H bonds are made by sp3-s orbital overlap 11. Which of the following has the greatest solubility in CH3CH2CH2CH3? A) CH3OH B) CH30'Na+ C) CH3NH2 D) CH30CH3 E) (CH3)3CH M 111. Which of the following has the lowest boiling point? A) CH3C1 B) CH4 C) CH2C12 P) D) CHC13 E) CC14 IV. The eclipsed and staggered forms of ethane are said to differ in: A) molecular formula B) configuration C C) conformation D) constitution E) stereochemistry V. What types of interactions are possible for (CH3)3N? A) induced dipole-induced dipole B) hydrogen-bonding C) dipole-dipole D) A, B and C E) A and C VI. The following compound would be considered a: A) ' 1 h 1 OH primary a co 0 C B) tertiary alcohol C) secondary alcohol D) an alkane Name: Last, First (PLEASE PRINT CLEARLY) 3. (10 pts) Confounding conformers a) Draw the condensed and line (skeletal) structures of 2-methylhexane. “ fl 7;; t‘ H (CH1)3CH:§ {HI/g /‘k/1\/ Y 9 {1’ . 1 y (ctr-5h c H cam maxim} . ,, 3 b) For the rotation about C3-C4 bond, draw the Newman projection of the most stable conformation. '0 r' L,H1C"‘3 H H \ n 8441996 (Cd 1'?) pk. ll C m, C H 9 C) For the rotation about the C2-C3 bond, draw the Newman projection of the least stable conformation. . at) . V) a,“ VH3 4. (8 pts) A smelly situation Butanol is being favorably considered as an improved biofuel or fuel additive, while butylamine is not. The boiling point (and smell !) of the amine, might be part of this reason. Provide a brief explanation why butylamine has a lower boiling point than butanol. (Hint: consider the types of interactions possible and how they might differ in the two molecules). b0‘H‘ Pan AF'Drrm ~ bCYM‘K-v am Cm M has -2)“ 9m) Mum” Wt MC MW M i 8 "mo/U» fix) Em ~ Edema/1L I” ms ‘l‘i’c y . (9?“ H v blind. Cc‘nwf) Cum 1 avnwg 4 Name: Last, First (PLEASE PRINT CLEARLY) 5. (16 points) The following Lewis/Kekule structures A-L are isomeric (same molecular formular CN2H2). To answer this question, begin by locating all of the formal charges and electron deficient atoms (atoms that have not achieved a full valence shell electron octet through covalent sharing). H\ LU rl ~i .. .. .. H_CEN_N_H (:CtN—NHZ HEN—GEN: C=N=N .. x/ a" " A ‘ B c H D N: :NH2 Heb—NE : H—N=C=N—H :c:_=_N—NH2 E F e H r .. @Qy 6—9 .. r“ W (H @ZN—CHZ H—CZNzN—H N:N—©H2 H—N—N=@}H I .1 K L Using this information answer the following questions, put answer in the box: _ i w I? (A) Which structures have no formally charged atoms. ‘ B) C I C4 I fl 0 1 (B) Which have at least one nitrogen With a (+) formal charge. A) D ; t [h H J, L / ‘ \ (C) Which have at least one nitrogen with a (-) formal charge? A) 0' E; ) K) L (D) Which have at least one carbon with a (+) formal charge? | k L i i i ’ i (E) Which have at least one carbon with a (-) formal charge? ‘ F, H, I: 5 l ) i (F) Which have electron deficient heavy atoms (N or C)? ‘ B M L I l l l _ ' (G) Which are the best structures based on our discussions in class C ( a .i and your answers above? . I? g _ Name: Last, First (PLEASE PRINT QEARLX) 6. (18 pts) An important anticancer drug Ixabepilone, shown below, marketed by Bristol-Myers-Squibb as IXEMPRA is used clinically for patients with metastatic breast cancer that has become resistant to Taxol. . If, (ii/1’51 Hug Ixabepilone a) How many sp2 hybridized carbons are present in Ixabepilone? b) Provide the chemical formula (CxHyOszSn) for Ixabepilone. c) How many lone pairs are present on all the oxygen atoms present in Ixabepilone? lo pairs 17’9" ned. Indicate this d) Ixabepilone has several ring structures, one of which is highly strai ” Discuss portion of the molecule in the drawing above with a box/arrow and the words “strained. briefly below why that portion of the molecule is strained. A r7 Owl 6W anch'zrm' ’ 4 3 1- pgdi‘a 7/1— th med 59/5 (gt/WM, G hat/Q l3ch mgHZ 73qu JVIIDF Mug ,bond oque was cmpmsrcfl *0 {were e) Though drawn above completely flat on paper, the molecule has a complex three- dimensional shape. Circle the portions of the molecule above where all of the atoms would lie in the same plane based on the type of hybridization that is present at the atoms. 3 p} .5 Name: Last, First (PLEASE PRINT QLEARLY) 7. (18 pts) Orbitals are everything (a) Draw both the Lewis and Line-bond structure formaldehyde, CHZO H _ i \ . ., r , . ‘ a ‘_ I 0 if, >59 or _: ~ ,‘ g t H it” k5; RAJ/Ml L421} (— , (b) What type of hybridization is present at the carbon? Place answer in the box: (c) What type of hybridization is present at the oxygen? Place answer in the box: ‘ 9131:] ((1) Draw an orbital picture of formaldeh de. Clearly label each bond type (sigma or pi) and indicate the type of orbitals (s, p, sp , sp3, sp) on all atoms involved in each bond. [Md 4 P” d {LLUVUL Co r N d H14 Name: LaSt: First (PLEASE PRINT CLEARL! ) Extra Credit (5 points tnax possible) Please only try this if you have finished the rest of the exam Petroleum jelly (like Vaseline) is a protect baby’s skin from diaper ras present in petroleum jelly?? semisolid mixture of hydrocarbons that is often used to h. Why does this work?? What sizes of alkanes are likely WMv we cm was flqf M W Wfifl mtuaut l7? ‘3‘. llbvbtj‘fi bottom 10(0le , {a m‘l’ivi‘flv AFC) mm Slave on C (th LU; H1402.” (“a {Li/(j)ng CM (9,, V‘Ofl» Cl? ’2 L1; (Liv i) m wcdfl‘ . (“'(i‘vé‘ I" with \ "ilkfi Hebe/s 8 lat n oncl (A HCl Cl (adj FOKVCVLQ (A Pa r VCLQ h mean“ be we s mi m Lt.«“‘»'\cj€ v a l (Lari as H lg ct Solid}: (71¢: (it Sc («we 9] “a ...
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8aS10Quiz1_key - Name: Last, First (PLEASE PRINT CLEARL X )...

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