Test_I_3331_A

Test_I_3331_A - First Exam Name (PRINT) Last, First...

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Unformatted text preview: First Exam Name (PRINT) Last, First Chemistry 3331 Signature _ September 27, 2002 '. 88# Please circle the name of your professor and class time where appropriate. Dr. Bean (TIT h 10 AM) Dr. Cai Dr. Bean (T/I'h 5:30 PM) TOTAL Note: Present your student ID when you return the exam booklet Il‘ 1. NOMENCLATURE: (15 points, 5 pts. each) Give an acceptab|e iUPAC name for each of the foilowing compounds. Be sure to indicate the stereochemistry where appropriate. am H b CHéinah H .m‘“ C. 2. For each structure given, draw the important resonance contributors. Circle the major contributor. (14 pts‘} *1 N(GH3)2 3. Place the following compounds in order of increasing boiling point. (1=lowest, 3=highest) (6 pts.) /\(O\/ M /\’/\/ 4. Circle the compounds that can lorm hydrogen bonds in a pure state. (4 pts.) QM <3 G0 fit 0 “—\NH Q00“ ' CHsCHe'g-H M F ———/ 1 E] 5. Place the following compounds in order of increasing acidity. (1=least acidic, 3=most acidic) (6 pts.) 0 o n ll CHBCHchENHQ CHacHz "G-O-H CHQCHg "C-NH2 [I E] D 6. Predict the products that would result from an acidi'base reaction between the two compounds below and place the answers in the boxes provided. Predict the direction of the equilibrium, and indicate the direction by placing an arrow in the box. {6 pts.) 7. For the molecule below determine the hybridizaton of the indicated atoms and place the answers in the boxes provided. (10 pts. ) + 8. For the reactions below, provide curved arrows to indicate the movements of electron pairs associated with bond breaking and bond forming, i.e., provide the mechanisms. (10 pts.) ?H3 CH3 u CH3 0. CH3 a CH --C-—-Br —y ' H20: ‘ x” H20: " ' 3 I CHs—ClH -—*+ ammo—~03 ——-+ CHamflJ—OH +H3c5i I H CH3 CH3 CH3 CH3 + Br' m- b. GHQ-"‘3: + OHS—Br “"1" GHQ—O—CHS + Br‘ 9. For the each of the following substituted cyclohexanes, draw the more stable conformation in the large box. Place the cyclohexanee in order of increasing stability (lzleast stable, 3—most stable). (12 pts.) unlit-J :1: l3} H3 nIlllC‘) ullllO I m \" CH30H2\“ 0H:on3 Cir-130142 D C] onchg CHSCHZ‘N. “"HoHeoHa Mont? 10. Draw an structural isomers and geometric isomers (cisflrans) resulting from theXbromination of ethyfoyclopropane (structure A). Place geometric isomers next to each other and circle them. (11 pte.) ACHECHS A 1 1. Consider the following reaction: (CH3)3CH + [2 4...”, (CH3)3CI + H1 a. Given the bond dissociation energies (BD E) below. calculate the overall AH° in the box provided. (4 pts.) b. Are the products or reactants favored at equilibrium? (2 pts.) Bond-Dr's satiation Bondnpfwociafim: 1| Energy ' Bond kcaL/mol Bond kcanOI ' HEX bonds and X-WX bonds Bonds to secondary cachet-15 . H_H 104 [m3)2CH“’-H 95 D—D 106 (CH312CH-F 106 F—F 38 (CH3)2CH—CI ‘ so creel 58 (CH3)3CH—-Br 68 Br—Br f6 (CH3);er 53 1—1 :6 {CH3JZCH—OH ' 91 1 i Bonds to tom'my carbons H; r 71 (CH3)3C HF l_06 HOuflH l 19 {CHalsc—c: 79 5 HO_OH 51 (CHShC—Br 65 (Cnggc—I 50 Methyl bonds (CLIENTS—OH 91 CH: “H 10“; Other c —H bonds CHs-F 1g: PhCHz—H (benzylic) as (3143:? 70 CH2=CHCH2—H (allylic) 87 CH: 1’ 56 CH2=CH ~—H (vinyl) 103 CH; *1 Ph mH (aromatic) no GIL—0H 91 ° 1 C "—C bonds Bonds to pnmary carbons CH3H_CH3 88 Egggz—H 13$ CH3CH2—-CH3 85 CHsEH2:§I 81 CH3CH2—-CH2CH3 32 CHaCszB’ 63 (CHabCH—CHg s4 2 '2 * )3C—“CH3 31 CHSCHQ—I 53 CHSCHg—OH _ 91 CH3CH2CH3—H 98 CHECHECHng 107 CHawng—Cl 81 CH3CH:CI{3——Br CHECHECHz—I 53 CI-I3CH3CH3—OH 91 I: ...
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Test_I_3331_A - First Exam Name (PRINT) Last, First...

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