exam 1 version 3

exam 1 version 3 - Chauhan‘Hanifl18l0204535

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Unformatted text preview: Chauhan‘Hanifl18l0204535 lllllllllllllllllllllllllIllllllllllllllllllllllll Exam 1 February 4, 2009 . SCORE Be sure to read each question carefully. Partial credit will be assigned where appropriate. 7. To receive full credit you must answer the question completely. Relax and good luck!! / l. 1 (10 p15) Draw structures for five c0nstitutional isomers that share the formula C4Hmo_ You do not need to indicate the specific bond geometries; simply provide each isomer’s general skeletal structure. WW NAME 2. (8 pts) Name all of the highlighted functional groups in the molecule shown below: 3, (8 pts) Complete the Kekule structure (i.e., write multiple bonds, unshared electron pairs, and assign formal charges where appropriate) for the following overall neutral molecule. Only (5-b0nd frameworks are shown. H H >0 4«,/ \ {Hg 4;: H H 5; l @ . 4 t 3’ «r«x ta) Né/i” 2 Wffl'l) 4. (6 pts) Name the following compounds in the spaces provided using IUPAC guidelines. 3' 77 K g {i p .U 5. (4 pts) Provide the appropriate skeletal structure for each of the IUPAC names given below: 4—sec- butyl-7—ethyl-5-ismpyl-2-methyldeca ne '5 6. (6 pts) Convert the following condensed stru - . Cturest sk l prowded belpwz 0 w 1n the boxes (CH3)2CHpt-IC(CH3)CH200H3 yV-K >/)\/"\ >/\\~»J/\é/L CH3CHZCOC(CH_3)ZCH2CQZH ‘ VT '7. (4 pts) Convert the following skeletal structure in toa line-b d all atoms. You do not need to indicate specific 31b ng that Clearly Shows 8. (8 pts) Draw a detailed valence orbital Sketch ofthe central carbon atom of allene on the template provided below. Include all of the necessary orbitals and clearly label each of them with the appropriate orbital designation (ex. 5, p, Sp3 etc). You only need to draw the orbital scheme for the central carbon atom, not all three. z‘ 9. (6 pts) Arrange the following compounds in order of increasing C—C bond length between carbons 2 and 3. (l = shortest and 4 = longest). 5/6 t W Jr? sr‘i’ 9/3 I??? if“? < f 3 2 3 _4 ""2 4 2 4 0/4 * _—+ 1F 1Aé/ 1W 1N Li ( if) Considering the structure indicated with a star above, the Carbon 2 e Carbon 3 sigma (0) bond is formed by the overlap of what orbital type(s)? Orbital Contributed by Carbon 2 Orbital Contributed by I\/ \a Carbon 3 10. (10 pts) Provide the appropriate product(s) or starting material(s) for the following acid-base reactions: @ e CH3CH29H2 + H804 t ' I 4 g , r . . . i . I - J-,-r t. i": "\ ‘ My _; / n. t r If ‘ . v 4,? . -f ; l . : . It, ' - / ,-’ 1, r / ' / ' Which of the following substances js/are strong enough to react complete (reaction favored from left to right) with NaOH? yfie pKa ofwater is 15.74. Clear cir e our answer 5 . ../' -‘ /" / , <9. / 9 fl / CH3CH2NH2 l- t g‘ Ethyiamine Acetone Acetic acid If pKa = 36 pKa = \ pKa : 1/. “x, /": K» ‘7 VJ/ f 7 11. (fipts) Provide all of the appropriate resonance structures for the following compounds. You do not need to 1ndicate electron movement to answer this question. Simpl draw the appropriate skeletal structures: G.‘ ‘ @ 12. (10 pts) Indicate the hybridization and approximate bond angles for each of the atoms highlighted in the structure below: Hybridization Bond Angles 13. (8 pts) Draw a three-dimensional line-bond structure of butanamine (see condensed structure below). Be sure to clearly indicate the appropriate bond geometry of all carbon and nitrogen atoms using wedges and dashed/ straight lines where appropriate. Indicate the polarity of the C-N bond using a directional arrow as well as partial charge indicators. CHacHZCchHgNHz Butanamine j—--/ i H‘ x- "2 ‘/ r / .EFmEaEw—Quczri 73.35;..— .£ 9.35. Ezcttm >KFEEH chufitum _ :rfiE h; EEC. 3:2...Zz 2:. :2. is is $2: 3 03.2“ v. :58 Em. a”de a 3 u own m. :32 m. .35 N. .932 >9 3:53 i. E B $3.an 9.: =2: umm: ma :5, m9. 962m EmnEzc BEBm E EcmEmB Hz mania mam wwEmc u=mE2m>m 9P. ............................. .- «I. --....-..- w: w: 2:. we 2:. E: m:— 25 25.53%: _>_ m: .5 mm 3 GE 52 EN. 35” is 5%. cm: can. 52. wiTNTw—n w.mf~m.$. “Tm—.mmé? «Tm—.mméfi firm—ATE. “$73.3. 73.3.5. 7.5.3.3. Wmfmné... m.:.wm.mr. m.9.wm.m—. WNTNWm—U w.f_..wm.m—. mu 5 cm ., E n. ESE £37m.“ «.mr.fi.m.~ 93.8 B an :— 33 m. m>onm 3cm NH wEmEEm Ev Iva 6 mucmmma 9: 36:00.. . m.wr.wm.wr. $2.3m...“ 3 no. .3 ma mSmdm m+ Wmmmdm ma 2. E amvmmdn m . duo.ka coEEou .o £25m VIN ll 3:539.ch :EEEm :55 m. as EOE 9.: B EwnEa... mme Ex .3. m: mwmszEma E 93:5: 332 “202 34:3 5 m- t m: 3 95.0 . coo S u 09 co cm.me Em mmmmmE u_E2m 02.2mm at...“ T _ooE>w me—m ccszxO thEmfi II. VI :QNr AI $85 2824 385$ 9.: B 2an 2.923; ...
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exam 1 version 3 - Chauhan‘Hanifl18l0204535

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