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Test_I_3331_A - First Exam Name(PRINT Last First Chemistry...

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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 aooeptab|e iUPAC name for each of the foilowing oompounds. Be sure to indicate the stereochemistry where appropriate. 0W- H b magmas H .m‘“ C. 2. For each structure given, draw the important resonance contributors. Circle the major contributor. (14 pts‘} *1 CH30\/\/ 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.) m <3 <3~c~s 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 CHSCH2CH2NH2 CHacHz "G-O-H CHQCHg "C-NH2 C] E] D 6. Predict the products that would result from an acidr'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.) (fHS CH3 u CH3 0. CH3 a CH moms: _,. ' H20: ‘ x” H20: " ' 3 I CHs—ClH -—*+ ammo—~03 ——-+ CHamflJ—OH +H3c5i I H CH3 CH3 CH3 CH3 + Br' .5— 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 cyclohexanes in order of increasing stability (lzteast stable, 3—most stable). (12 pts.) mum :1: l3} H3 ”IlllC‘) ullllO I m \" CH30H2\“ CHQCHQ CchHg D C] CchHg CHSCHZ‘N. ""troHeoHa Mont? to. Draw alt structural isomers and geometric isomers (cisftrans) resulting from theXbromination of ethyfoyclopropane (structure A). Place geometric isomers next to each other and circle them. (11 pts.) ACHQCHS 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 Bonanfssociaz-fon 1| ___§___g3__ Energy ' Bond kcal’mol Bond kcab’mol ' HEX bonds and X-WX bonds Bonds to secondary carbons . H_H 104 [CH3)2CH-—-H 95 D—D 106 (CH312CH-F 106 F—F 38 (CH3)2CH—CI ‘ so ClflCl 58 (CH3)3CH—-Br 68 Br—Br f6 (CHQZCHwI 53 1—1 :6 {CH3JZCH—OH ' 91 3:; i3? Bonds to tom'my carbons 11:1 r 71 (CH3)3C HF l_06 H0——-H 1 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’ 55 CH2=CH ~—H (vinyl) 103 CH; *1 Ph mH (aromatic) no GIL—0H 91 ° . C "—C bonds Bonds to pnmary carbons CH3H_CH3 88 Egggz—H 13$ CH3CH2—-CH3 85 cnfinig 31 CH3CH2—-CH2CH3 32 CHECHEWE 53 (CHabCH—CHg s4 2 '2 * (CH3 )3C—“CH3 31 CHSCHQ—I 53 CHSCHg—OH _ 91 CH3CH2CH3—H 98 CHECHECHng 107 CHawng—Cl 81 CH3CH:CI{3——Br 68 CHECHECHz—I 53 CI-I3CH3CH3—OH 91 I: ...
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