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322asu09_e1_key - CHEMISTRY 322aL Please K E Y EXAM NO 1...

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Unformatted text preview: CHEMISTRY 322aL Please K E Y EXAM NO. 1 Print Last Name JUNE 1, 2009 First Name @0117 A) 6/ First 4 digits of USC ID _ _ _ _ ‘XXXX-XX / ——.__—.._——__ name of TA Grader (1) (20) __ (2) (15) __ __ (3) (20) .__ _. (4) (20) __ __ (5) (15) __ _____ (6) (10) .... __ (100) first letter of last name I will observe all the rules of Academic Integrity while taking this exam. Signature Chemistry 322a -2- Name Exam No. 1 (1) (20)) Answer the following questions. (A) (4) Provide detailed dash-line structural formulas inside the boxes for the two organic molecules written below as condensed formulas. Your detailed structures must show all the atoms and all the bonding and nonbonding electron pairs. Show each pair of bonding electrons as a dash or line and show each nonbonding electron pair as dots. (CI-I3)2CHCHC1CH3 CH2=CHCH2CHZOCH3 B.- (B) (2) Draw inside the box to the right, a bond-line structural formula of the condensed formula below the box. CH3CHBI‘CH2CH2CH(CH3)2 (C) (6) Provide the missing charges on the structures below, Where all the valence—level electrons are shown. Place the charges immediately next to the atoms on which they reside. (D) (8) In the organic compounds below, identify each functional group by selecting the proper name from the list of choices and writing it on the line next to the arrow. la. . kgi'O'ng cm \QPL/ “\CO he \ W in 0—0 9K CH3CHCH2CH3 M93 CH3CH2COOH CH3CNH2 CH3CH2CH2CH = CH CH N(CH ) CH C~CCH 3 2 3 2 3 3 m \éibL—V— 2942;35— Choz’ces: alkene, alkyne, alcohol, aldehyde, amide, amine, aromatic, carboxylic acid, ester, ether, ketone. Chemistry 322 -3- Name Exam No. 1 (2) (15) Answer the questions below. (A) (6) There are three constitutional isomers of C3H80. Draw the condensed structural formulas for these isomers in the boxes below and provide the alkyl group name for each on the line below each box 0 H ‘ I CHSCHfoit-k CH3CHCH-3 C\~\3<H20<H ‘ grueg‘\ o~\qokol lSofimPgs alcohol e_+\\:q\ mo.%l S'HAQV (B)(9) Answer the following questions about HZCO. (i)(2) Draw a dash-line structural formula for HZCO inside the box below. Show all bonding electron pairs as dashes and all nonbonding electron pairs as dots. (ii) (2) What is the geometry around the C according to the VSEPR model? +V\% D'“°'K (Ela‘na [: (iii) (2) According to the hybrid molecular orbital theory, what is the hybridization of the carbon atom? 2—. ___§_L__ (iv) (3) Draw and label the set of orbitals for this hybridization using the axis system below.. Chemistry 322a -4- Name Exam No. 1 (3) (20) Answer the questions below. (A) (8)For each of the three structures below, add any missing formal charges immediately next to the atom on which they reside. Draw a geometrically correct structure for each compound or ion inside the appropriate box. Write a geometrically descriptive term or word inside each box. (B) (8) The table below lists some bond dipole moments. For each pair of compounds below, circle the one with the larger molecular dipole moment based on these bond dipole moments. Draw geometrically correct structures of the compounds in each pair with bond dipoles and explain how you made your choice. Bond Dipole Moments OH 0.30 D C—F 1.51 D C-Cl 1.56 D (nu CC13F F 3 A d l H on \PD 4—3 B, «A A ~ Q\ MOS+ (Q'WCJL.\ Leobg [email protected]/%U\‘& C‘LX/Cfiq‘ Cl (B) (4) Indicate whether the following pairs of structures are the same compound (8), constitutional isomers (C1), or two different compounds that are not isomers (NI). Write your answers on the lines below the pairs. H 1 H H C 3CHCC (C 3)2 {:>»CH3 H2C=CHCH2CH2CH2CH3 5 Q1 Chemistry 322a ~5- Name Exam No. 1 (4) (20) Circle the correct answer for each question or statement below. (A) The numbers of valence-level electrons in the two ions below are (circle answer below) + NO ‘ CH3l;lH3 H 3 I 15’ II 23 I 14, II 23 11511 24 (B) The molecular formula of the structure below is (circle answer below) DOE]: C5H6O C5H7O C5H100 (C) The isomers with the higher boiling point (pair A) and higher melting point (pair B) are 9H3 \"C\ H3C\ CH CH3CH2CH2CH2CH3 CH3CH=CHCH20H CH3CH2CH23'T H3C/ 3 gLTL/ W A (higher bp) B (higher mp) (circle answe A I, B I A I, B H A II, B I A II, B H (D) Among the labeled C-C bonds in the three hydrocarbons below, (circle correct statement below) A A is the longest and the strongest. l B is the shortest and the weakest. B CH3CH2 —CH3 H2C=CHiCH3 HCEC CH3 C is the shortest and the stron ; est. A is the s ortest and the strongest. C (E) In each pair below, which structure has the larger dipole moment? F F C 1 (circle answer below) \ C \B—‘F B“H kczc/H l\C=Cf: A I, B I A I, B 11 H \ AILBI (AILBII ) I II L_____V—_J \———-\/———-—/ A B Chemistry 322a —6— Name Exam No. 1 (4) Contd. (F) What is the relationship between the structures in each pair below? ‘ ‘ -- 9).; H’EQ -- H/Kk H H‘ ‘—l'\l_H H—C—N‘H __N_H I—{C__$: H a «CI HH \____V____J L___W___/ A B (circle answer below) —A and B both have structures that are constitutional isomers. - tures. «-A has resonance structures while B has constitutional isomers. -A has C0115 I ona ISOmEI‘S W l e has resonance struc UI'ES. (G) Identify all the secondary amines among the structures below. NH (circle answer below) 2 CH3CH2CIJ(CH3)2 CN-H CH3QHNI-I2 (CH3)2NH 1,111 only 111 CH3 only IV I II III IV (H) In each pair of structures below of comparable mass, intermolecular attractive forces will be stronger in CH3CH2CCH3 CHgCHZCHzCHZCH3 CH3CH2CHZOI—I CH3CH2CI MW 72 72 MW 60 64 \ I 11 / . 1 11 , A B (circleanswe ALBr ALBII AII,BII AILBI (I) When acetone (see below issolves in water, the solute-solvent interactions will be a combination of which of the following types of intermolecular attractive forces? CH3§CH3 ion-ion ion-dipole dipole-dipole hydrogen bonding acetone I II III IV (circle answer) II and III II, III, IV I,II and IV (1) Which of the following diatomic molecules are "ir active"? (circle answer below) C1-C1 H0 H2 N2 CO I d II I III d IV I II III IV V a“ ' an II and V II, IV and V Chemistry 322a -7- Name Exam No. 1 (5) (15) (A) (5) The anion C3H5O- has the linkages shown in the box below. (i) (1) What is the number of valence-level electrons in this ion? 2 E (ii) (4) Draw two different resonance structures for this ion in the box above by adding the missing electrons to A and B. Each structure must obey the Octet Rule. Clearly show the location of the negative charge in each structure. (B) (10) Identify each pair of structures below as resonance structures or constitutional isomers on the line below each pair. . - + + . , . . CHg-Q‘CHZ CH3-Q=CH2 H2C=CH "NHZ CH3-CH=NH PCS om’kgc Sfig‘hv‘d comsji‘ku {1mg 35°,“ch : : :9H CH3—CH=CH-3H H2C=CH-CH:CH ng H3 CH3 CH3 \‘1S0’ncgmkl S+Pve4cvr~cs Chemistry 322a —8- Name Exam No. 1 (6) (10) Match the structures below to infrared spectra in the Appendix, as requested. (A) (5) Assign each of the three structures below to infrared spectra in Appendix A by writing the number of the spectrum on the line below the structure. In the shadow box, briefly indicate the characteristic absorptions in the spectra that you used in making the assignments. assignment benzene cyclohexene cyclohexane spectrum no. “T T \ \-Q\\ C~+\ S’fin‘tck belong 3000 Qm~\ Z n Shel—OS C‘H Sfig‘fl-e‘k loci—iota, (AKA CL\QD\J§ 1000c; g " CL\\ C.-\‘-\ S'JH’I‘h-gk CI..\'QDV( ’chzo waf‘\ (B) (5) Assign each of the three structures below to infrared spectra in Appendix B by writing the number of the spectrum on the line below the structure. In the shadow box, briefly indicate the characteristic absorptions in the spectra that you used in making the assignments assignment cyclohexanol benzyl alcohol cyclohexanone .. “T— SLOHD‘S 8"!»me Sfim‘kuM Midi-P \7ou aK‘ .Qh Q=o spectrum no. q- E" SMOHDS \phomé “bier-DHO‘N 73290-3L¢OCM.( ~COA OH amé u\\ Cf—R S‘i‘m‘kgk b7..\O‘-Q Swoqh~k hakd $2.96 ~3~goo wa“ —ér~ 0H, C: Q SL‘DHJS broqg‘ Cgfm$ ‘ C—H stuckbx \S QLMK 4—\.¢\OQ 3°°°<wi\ Chemistry 322a Exam N0. 1 E E E 3 All ¢~H 4000 < 3000 CM" M +50%” b NM (05008 ?000 TRAN SM ITTANCE -9- Appendix A Infrared Spectrum 1 3000 2000 Wavenumber (cm-l) Infrared Spectrum 2 ‘3000 J 2000 Wavenumber (cm—1) curl infrared Spectrum 3 w 2000 1000 Name Chemistry 322a -10- Name Exam No. 1 Appendix B Infrared Spectrum 4 0.8 LLI g 0.6 E 3 0.4 l— E \ E 0.2 V S C 2 O 0 0 _ \ ‘ 3000 2000 1000 5%." N17 3'0 CM / Wave-number (cm-1) Infrared Spectrum 5 0.8 5 0.6 01/ E 5 0.4 O E ’- 0.2 3000 2000 1000 (La C‘H { rh- < ?w%w;~/I Wavenumber(cm-1) Infrared Spectrum 6 0.6 0.4 TRAN SMITTANCE 0.2 4000 3000 2000 1000 3 Wavenumber (cm-1) ("17/ 51‘» «AN? 1“ LAW- 3000 cm/ ...
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