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mt1 - Chemistry 118A Winter 2008 First Midterm Tuesday Jan...

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Unformatted text preview: Chemistry 118A Winter 2008 First Midterm Tuesday Jan. 29th Instructor: Lievens This exam contains seven (7) pages and three (3) sections. Please make sure that your copy contains all seven pages. If there is a problem, please tell the exam administrator prior to beginning. Please answer all questions. Remember that UCDavis Code of Academic Conduct applies to this exam and all other graded work in this class. Name: Student ID. # T.A.l Lab Section: I. Nomenclature: (14 points) Give the IUPAC name for each of the following compounds, or draw the correct structure for the given name. (EHZCHS (EH2CH2CH3 1} A) H3CH2C'CE‘CH2CH2C"CHZCH3 3 ,3'L-1'r‘e‘h‘yi ’ (rme 7] NM s-e (3+4ch3 CH3 2 ,€-o\'.\o«omo - 1.. SW - Z." We flock.” B) , \ 3Ji\$°i"°t"l‘ CydaMXC‘N C) 1 3 A; (4 me’fkyl e‘hay‘ )Cydahem I—,3 56" 3 max ilehyncydo‘flemue D) m 5' Homo ' S’C‘Wlara Veto/[-2 2-”. e111,! OC‘IH‘L E) :3:>< 3]” -A1‘(er10vb-l,1-Cjimeh\y' 0/40??th Br F) 1,1-dibromo-Z-chloro-S,3-dimethylcyclobutane / B, C H3 CL G) 1 ,1 ,2,2-tetrachloro-3,5dimethy1hexane Cl C\ 7 Bonus +2: - W 1' 56013051 ';~I'Sopf°Pyl 4-531:li Cyclfikeptnnz 2&5 tsdcww-z (smwen,t>-1 (ImeMpmpyu NW C Yc tokepk N. ’\ 32w Keno“ W W211 Wmmmmn wrangoroler 2. Vocabulary: (30 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) A nucleophile is considered to be electron f l d" . B) A pi bond is made when two 2 orbitals overlap. C) Electronegativity increases as one goes g 29 t Y! gh‘l on the periodic table. D) The activation energy of a fast reaction is relatively large B) E romm is the least reactive halogen that will still form products in radical reactions F) A bond that has an electronegativity difference of less than 0.3 1s a flQn Qolar covalen'l' bond. 1 £91 radial while a double G) In a mechanism a ‘fishhook’ arrow represents headed arrow represents 2, £9 Z Q YT! 0 V» H) An atom that has more than eight electrons 1n it’s valence shell has an ego/MAM OCH 1) A reaction whose products are higher in ener starting materials will tend to be Chdoh‘ erm 1C. and have an early @F/tmmtion state J) An electrophile IS likely to have ’negative charge. K) The London forces that hold alkane o gether increase with 7‘19». 0 r S" 2 g L) A Lewis acid g (Ciel-:5 electrons. M) The reaction of methane with fluorine radical has car / late transition state and is endothermic exothermic. N) Ansphybridizedcarbonhasa \ingar shape. 0) The ener it takes to rotate a carbon carbon single bond is {Qijfingz or irgiami energy and it increases wi larger smaller groups in a phenomenon called fi rig= Mintfil {61th Z ${Sl6fl‘e She/H P) Which will boil at a higher temperaturqoctane Dpropane? Q) All lewrs bases are nucleo a~h11e False. R) Primary / secondary .ydrogens are most likely to react in a radical reaction. S) Eclipsed @nformers are lower 1n energry. For butane the lowest ener co ormer isifb____ T)fl Cg r9 \¥h£ cleavage breaks a bond leaving each portion of the T)molecule as ions. U) The phenomenon that allows neighboring alkyl groups to stabilize a radical is r n u on» V) What are the names of the three steps in a radical chain reaction? ‘1 l when Yo ‘k’rmska \?3f \DQF 0:03th (Lift ”th5 )% \YK OWSWJQY is \{m gran)“ ‘ 3. Short Answers: A) What is the hybridization at the indicated atom (6 pts)? 3 v C D \N\£W 5 2/ O/CHa <——— F A\ i I ’Z A: ,5}? B= 523 C= $32 \P\‘eg\c‘/\ D= $533 E= 532 F= 523 B) What IS the shape at the indicated atom above? (3p) A= lmeor B= mwdn—UW'J’ C= {nggm-Q flower; 5M— D= filmlnedvd— E=1ln )aNr F= {YEMAM-‘Q ‘Qaclq C) Look at the following molecules. List two functional groups for each molecule. (6 PS) 0 1101 1/“ 1§1w A= egg! B= (1)1114: C=_% :Carloomflakmid A= 0.99:1an B= alkyme c: GMlV-L or ' (Aldo/0a, [<4 hL/ 1% loalkmu— qh/Z D) Using Newman Projections show the six major rotamers of the C-2/C—3 bondof ' 2,3-dimethylbutane. Indicate which are staggered or eclipsed and indicate the relative energy of each confoxme: using a potential energy diagram. (8 pts) Bonus: Which rotamers have the Hydrogens anti / gauche. B,D,¥ —> sawed A E '7 H 04),; T: *7 HEN 52 IP+€ACL E) Draw the Lewis Dot structures of the following molecules. Show the major resonance structures. (6 pts) HC03- (0'. .. G) 2: :0: 19 6.61C 0‘ (‘7 ...C.. . w a u H :.C')I ‘QH J CH3CN H H:C; c.::N' H CH3C02' ff 0,6 ,4 9: Q chuCL‘ 6-7 H;C'C, “é lv ’0'. H '0. F) Show the possible products of the following radical reactions. Indicate the relative abundance of each product (10 pts) 3 ad: 1x5“— \JY m2 7 21 /q-— 3 ‘ 3x1: 3 / WKS: Cl W\Q\ (“lg Q: ._ Br Ar\ Bur2 (0x129 , . _ 9x86: 310 , hv /\r\\ o 5/5l‘mcl71fe. gr ‘ .S'l CofltC—l QEUHAGHLQ Ab /\(\ B - M700 .— 3“ ' 3 zI700 G) There are eight possible constitutional isomers of the formula CSHnCI. Sketch their structures (8 pts). H) Which of the following are electrophiles? Circle them (3 pts) 1 e6“ d" @ Ne OH' _ CH3C1 NH3 H20 ‘ @ I) Which of the following are nucleophiles? Circle them (3 pts) H+ 61—1) BH3 €39 CH3I @ N; l each I) Show the bond-line structures of the following molecules (4 pts) ‘ (CH3)2CH.CHOHCHCHCHO 6H C? 3‘" H O CH3CH2CHC1CHBICH2NHCH2COCH3 /\/l\/N \/ll\ Cl CISGPl‘mhs 6k, K) Sketch the moiecnle C2H2 showing all bondin orbitafs with their proper sha 2g 3 PC and orientation. Label each orbital as s, Sp, sp , sp or p. (8 pts). Bonus label each bond as 0 or 31:. wage—41 \vt oer Correcjflj wow“ I labeldi d rhino. on C- ...
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