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322as05_e1_key - CHEMISTRY 322aL ‘ Please EXAM NO 1 Print...

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Unformatted text preview: CHEMISTRY 322aL ' ‘ Please % EXAM NO. 1 Print Las Name FEBRUARY 7, 2005 N First Name USC 1D K \ name of TA Grader (1) (20) _ (2) (10) E __ <3) (20) __ .— (4) (15> _ a (5) (20) __ ' __ <6) (10> _ __ ‘7)((f§3)— __ first letter of last name I will observe all the rules of Academic Integrity while taking this exam. N Signature Chemistry 322a -2- Name Exam No. 1 ' (1) (20) Answer the following questions. (A) (4) Provide detailed (dash) structural formulas for the two organic molecules below written as condensed formulas. Your structures must show all the atoms and all the bonding and nonbonding electron pairs. Each pair of bonding electrons must be shown in the dash or line formulation, while nonbonding electron pairs must be shown in the dot convention. Place your answers in the boxes. CH3CHC1CH=C(CH3)2 (B) (2) Draw inside the box a bond-line (abbreviated) structure of the condensed formula written below the box. (CH3)2C=CHCH2CH(CH3)CHzBr (C) (6) Add any missing formal charges to each of the following structures. Place the charges immediately next to the atoms on which they reside. (D) (8) Select the correct functional group or family name for each organic compound below from the list of choices. Write your answer on the line below the structure. CH3CH2N(CH3)2 CH3CH2COCH2CH3 CH3CH2C ECCHZCH3 (mu—ng CS‘l‘tr CA\\<:(1\$ gut-lag: Choices: alkane, alkene, alkyne, alcohol, aldehyde, amide, amine, aromatic, carboxylic acid, ester, ether, ketone, nitrile. +—+fi Chemistry 322a -3- Name Exam No. 1 (2) (10) Answer the following questions about C02. (A) (2) Draw a Lewis structure for C02 in the box below. Your structure should show all valence-level bonding (as dashes) and non-bonding (as dots) electrons. Lewis structure for C02 (B)(2) What is the geometry of COzaccording to the VSEPR model? \ {Mun- (C) (3) Within molecular orbital theory, the bonding in C02.is explained using the atomic orbitals of an sp-hybridized central carbon. In the box below, draw and properly label the valence-level atomic orbitals of an sp-hybridized carbon using the x,y,z-coordinates. atomic orbitals of an sp-hybridized C (D) (1) Does C02 have a zero or non-zero dipole moment? 2‘ QFQ (E) (2) The several normal modes of vibration of C02 include a symmetrical stretch, asymmetric stretch and a bend, shown below. Which ones are IR active? We.“ L Chemistry 322a I -4- I Name Exam No. 1 (3) (20) Answer the questions below. (A) (10) Indicate whether each pair of structural formulas below represents the same compound, constitutional isomers, or different compounds that are not isomers. 9H 9*?» CH3CH2CHCH2CH(CH3)2 CH3CHCH2cH0H WA CHZCH3 ’L CH2=CHCH2CH2CH3 O ' ' rs ac A/ O 0 II II CH3CH2CCH2CH(CH3)2 CH3§ZHCH2CH2CH2CH CH3 MW SMK COK$OU«A_ l (B) (6) Provide names for the three compounds below using simple alkyl group (common) names. fill CH3CHZOH CH3CHCH3 CH3CH20CH3 \\ Odo \ Wage; M\ (‘r av- (C) (4) A secondary amine has the formula C3H9N. Draw its condensed structural formula in the box below and write its name (using alkyl group names) on the line next to the box. 3 /x j ff“, 6) QHscHzNHQH3 q-l-lt d' ‘ fig i/L mm , W 4/ M7“ 2/0 amuse Chemistry 322a ' -5- Name Exam No. 1 ‘ (4) (15) Answer the questions below. (A) (6) With reference to the information in the Appendix, provide the products of the following acid—base reactions in the correct boxes below. Where metal ions are shown in the reactants, include them in the products. Use condensed structural formulas for the products. l CH3CH2CH2CH20H + H2504 *—. +/ CH3CCH3 + NH3 ® + H80? conjugate base + 3c CH3 (+3 conjugate base H conjugate acid CH3c'ffi2 Li+ + CH2=CH2 CH3QH 3 conjugate acid conjugate base (B) (5) For the reaction below, draw curved arrows that show the movement of electron pairs, and add any missing charges to the reactants and the product. Identify each reactant as a nucleophile or electrophile on the line below the structure. (C) (4) For the chemical species below, draw in the boxes geometrically correct structures, based on VSEPR theory. Note, nonbonding electron pairs are not shown, but must be considered. On the line below each box, write a descriptive term for the geometr . Chemistry 322a ~6- ' Name Exam No.1 1% A, ' W (5) (20) Circle the correct answer for each question or statement below. (A) The molecular formula of the structure below is 71' H C71‘110O -C7H14O C7H16O (B) In the hydrocarbon below, the carbon-carbon single bond lengths are in the order (longest to shortest) CH3 (circle correct answer below) lJ A>B>C B>A>C HCE C— Q“ CH: CH2 < B>C>A ) A>C>B (C) The compound with the highest boiling point among those below is H (circle answer) 0 0 MW 86 84 84 (D) The least polar compound among the fluoromethanes is (circle answer) CH3}: CHZFZ CI'IF3 (E) Among the isomers of C5H12 below, the one with the highest melting point is (circle answer below) 9H3 CH3CH2CH2CH2CH3 CH3CHCH2CH3 (circle correct answer below) W Chemistry 322a -7- ExamNo.1 ZWA‘ 0% x (5) (Contd) (F) Accordin g to the information provided, the stronger bases in the pairs of compounds below are (circle answers below) 0N aniline and pyridine aniline and a d - Ka c cloh- -x lamine and . ridine aniline cyclohexylamine pyri23dine pyrimidine cyclohexylamine an- pyrimidine PKb 9.4 2'70 (for the conjugate acid) (G) Among the four alkyl bromides, C4HgBr, below, the primary bromides are (circle answer below) CH3CH2CH2CH2BI' CH3CH2CHBI'CH3 (CH3)2CHCHzBI' (CH3)3CBI onlyI land II I 11 III IV only IV (H) In the compound below, the order of acidity (strongest to weakest) of the bolded His (circle answer below) H ® FHOCHzCHZCHzgl-IEOOH AC A>C>B - C>B>A B>A>C A B (I) Which structural feature below is most c onsistent with infrared spectrum A in the Appendix? (circle answer below) (PH RCHZCCHZR' RCHZCH=CHCH2R' RCHzC ECCHZR' RCHZCECH RCHZCHR' (J) Which structural feature below is most c onsistent with infrared spectrum B in the Appendix? (circle answer below) 9 pH RCHZCCHZR' RCHZCH=CHCH2R' RCHZC ECCHZR- RCHZCHR' Chemistry 322a ' -8- Name Exam No. 1 (6) (10) Answer the questions below. Only one compound has ever been isolated (compound A) with the condensed formula of I, but there are two isolable compounds (B and C) with the condensed formula of II. (A) (6) Carefully draw geometrically correct structural formulas of A, B and C in the boxes below. Use the wedge convention to show three-dimensional structural features in A. For B and C, provide complete names on the lines below the boxes. ClCHZCHzCl ClCH=CHCl 1,2-dichloroethane 1,2-dichloroethene C\-n\l Cont» rwth')“ cLs—\ \Z‘dfclm\°m \g O (*4me + vet—ms - l .‘L-dt older-mfg (B) (4) Use the molecular orbital description of covalent bonds to explain: (i) why there is only one compound known with the condensed formula of I. The. Covcc\a~c\- bomd COthefimi +k( Cox‘oo-KS vvx I. \S Q S\5‘mq bond gnome—L Q‘OMOVRP\¢L'P 01$: SP3 ac‘l-DMI‘K OrlorchS, SK‘J‘MO. komdg ark C1l\¢\dr\\c~\\¥ S¥MML+P\§_§.\ C~\o$ +l~§ \oo'nA Cogs~ Qo'K-LHC’K OCCUr—S. A\+\\°Uj\v\ (if z area—uses“ «1—3- mx SPd-LL ahk ¥v€31bl< GP 1k!- sérovxs ‘an—x, macros? (ii) why there are two known compounds with the condensed formula of ll. 0 \J 1- low: AKS' Tkg doublk how‘i \S No.41 up 0‘?“ 0. S‘SMK LOAA 0Q T‘D‘l'G-"C’fb'x 'R'DhmbUIr-Kkp cg SQZ owbfin.\3 GWAQK‘TJ beA. 'G‘DM own-k? a-Q— P a—fl-umxg ohbc‘nAS‘ Tu.“ ‘3 CL \QEK \DCu-r-‘tafi +0 W'l'zrl'w‘o’xq Q.\Oq\% +\.‘¢ csqu CO'AW V'lxg Cow-BOms \DO—Qaucs:\ OUIC‘KL? af- +L1 \S ,DST. The. lace—5K \qur‘qw “9““: +K+_ 'H‘K Chemistry 322a ‘ -9- Name Exam No. 1 _ (7) (5) Draw the two important contributin box below. Be sure to add all valence any formal charges in your structures g resonance structures of nitromethane in the -level electrons (bonding and nonbonding) and show CH3-N02 itromethane 3 According to the resonance structures, what is the bond order (number of covalent bonds) between the central N and each 0? \- '5 .L What is the charge on each oxygen? 2- 6 Lack IR Spectrum A Jr 1’6 ”/7! If? Percent transmillnnlcc I’crchII Imnsmiuancc Appendix 4:C 51‘? “’0- “-1 -- ——...____- .._ -.._+-_._.______ :1 gm , I III a. III I. —- (IO— ' I Iom 50m 51m- MI 2m 2000 mm IMO mm 12th I030 H)" 503 W: l\ cnumbcr (cm") 100 ‘ I i ‘ I I I I W ____ _I_ L I I I __I I I I I I-I—'T I I I I m, __ _ 1.1.4 .L__L_I_.- _. . _L_ _~ . i ; I 1,- I _ _1_ 4- .;._f__2_ - _I__.._ ._ I ' I ‘ I I ‘ ' f I z m - - - + — “4““? I—%— ———!—-+§- — — fin - —_ _ _ _;__i_ ’_;__ ._ . i ‘ I ' ' I V 2 : I I- i I I 1. —. __ 144%? 1.1-1.1-- ‘ . I I I ' I I I I In —-— - ~ .--—~-°--‘—-—7—.‘-—-—'——~&—'—- I I I I I I I 3 I I I“ __:_l __ ...._.L_ I l ‘ “—3.“... i I“ I I f I I 10 —~ — «-—— — —— - —---——~—:f——§-;--r —§——L———— —- n I I I i I I I MW... ..,...l...(...,'...,..= 40‘“ 5mm 5:00 :30" J-IIXI :00" man loot) MOI) 1:00 1000 800 can \V’m-‘cnumbcr (cm' l) ...
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