Spring 2006 - D Please check here if you wish To have your...

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Unformatted text preview: D Please check here if you wish To have your exam reTurned To The boxes ouTside The classroom. Exams noT reTurned To The boxes may be picked up aT Professor Gray's office (487 KolThoff) during office hours (2:30 - 3:30 M'W'Th'F). LasT FirsT Name Name QuesTion 1. (please print clearly) 2. ID. number 3. Organic ChemisTry 2301 Exam #1, February 15, 2006 4. Professor Gary R. Gray 5. 6. Please answer all questions in the space provided. You may 7. use a calculator but not molecular models or notes. 8. ToTal The exam must be taken in ink in order to be submitted for re—grading. 1. (10 poinTs, 2 each carbon atom) PredicT The hybridizaTion of each carbon aTom in The following compounds or ions. Note: Unshared elecTron pairs are noT shown. a. C02 b. [H2COH]+ c. HCN d. [Hzccm' 2. (14 points, 2 each) Assign formal charges To the individual afoms fha’r bear Them in The following compounds or ions. All unshared electrons are shown. If there are no formal charges, wri’re “none.” T a H—c—H b H—?—CEN. H H H H u H A 5 H H A /q H H H n 'I I e H—C=f-H f H—c—N—c—H H H H—c—H H H—C=C—C—H 9 I | | H H H 3. (8 poinfs, 4 each) Give The systematic names (IUPAC rules) of The following compounds. $H3 sz‘CH3 a_ H3C—f—CH2-f—CH3 H H C(CH3)3 CH3CH2 4. An unknown was found to contain 56.4% carbon, 8.29% hydrogen and 16.5% nitrogen. No other elements were detected (oxygen was not analyzed). a. (8 points) Calculate the empirical formula for the unknown. You must show your work! Note: C = 12.01, H = 1.008, N = 14.01, 0 = 16.00. b. (2 points) The unknown was analyzed by mass spectrometry and found to have a molecular weight of 85. What is its molecular formula? c. (1 point) How many elements of unsaturation does the compound possess?. 5. (12 poinTs, 6 each) Draw The Two possible chair conformations of The following SubsTiTuTed cyclohexanes, labeling each of The subsTiTuenTs as axial (a) or equaTorial (e). In each pair of conformations, circle The one ThaT is more sTable or if The conformaTions are equal in energy, so indicaTe. a. Q (d5) H36 CH3 CH 3 b_ (Trans) Br (20 poinTs, 4 each) For each of The following compounds or ions, give Kekule’ sTr'ucTur'es for' The impor'TanT resonance conTribuTor‘s. IndicaTe which sTr‘ucTur'e is The major conTr‘ibuTor‘ or' wheTher' They have The same energy. a. H2CNN b. [HZCNOZJ' C. N02— (16 poinTs, 4 each) For each of The following compounds, indicaTe The number of elements of unsafurafion presenT in The compound and draw a Kekulé sTr‘ucTur‘e (elecTron pair‘ bond shown as a single line) or line angle sTr'ucTure of a compound having ThaT molecular formula and The indicated funcfional group. a. C2H7N (2° amine) ElemenTs of UnsaTuraTion: b. C3HyBr (2° alkyl bromide) ElemenTs of UnsaTur‘aTion: c. C3H60 (aldehyde) ElemenTs of UnsaTur'aTion: d. CeHeO (aromaTic keTone) ElemenTs of UnsaTuraTion: (9 points, 3 each) Give the structures of the products of the following acid- base reactions. From the pKa values given below, predict whether the equilibrium will favor the reactants or products by writing "favored" under the reactants or products. _____91<a________r£°_ H2504 -5 H20 15.7 CH30H; -2.5 CH3CH20H 16.0 NH4+ 9.4 NH3 36 CH30H 15.5 CH3NH2 40 a. CH3CH20H + CH3NH_ : b. CH3OH + H2504 ‘_‘— l c. H20 + NH3 ‘—— it!»— §E5@ .EEBIEEIIEEua-flfliggfifluilsgigigisgglggg I: h: +m m3 .3 N3 02 SH 22 2: En— mm mm— wa "—U a xm E a E< «a 3n. ma a2 .5! Ella. ii. all! i RN NE SN in: = .5 E .5: c: 55 2: mm i Sufi mcH Dn— flip + 3 tn. 1” 3 an ,4 . 3 i ‘ RSNNN mania 333: Sn: 35% w QM. Em fit: an: “hun— hh h— finan— lb: 55.2 i! MN +m . +u 3 +m 3 $ I a 2 +N 3 L we . 3.3 325% «was 32:3 3.5 “:33 «UP N'OEHCA—z O'hN QM> “Mum hMA—M— . +N 5 +m 3 +~ 3 4m 3 z 3 ¢ m." +m 2 , $88 “in... 3equ $2.3 33.8 8.: flamma: . wN—z RNA-U UNOEmfln-E 'Nhnv MN> NNFF HNUW a muhdw fins 3N BU .— hahudm 6H M2 . <=> <_> <> <2 <___ a a a s a 3:050? 93 mo 3&3 Ummuoiom mlSOMO—Z ...
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This note was uploaded on 10/30/2011 for the course CHEM 2301 taught by Professor Gao during the Spring '07 term at Minnesota.

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Spring 2006 - D Please check here if you wish To have your...

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