exam-1J - First Exam Name(PRINT Last First Chemistry 3331...

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Unformatted text preview: First Exam Name (PRINT) Last, First Chemistry 3331 Signature September 27, 2002 SS# Please circle the name of your professor and class time where appropriate. Dr. Bean (T/T h 10 AM) Dr. Cal Dr. Bean (T/l' h 5:30 PM) TOTAL Note: Present your student ID when you return the exam booklet I‘L‘ 1. NOMENCLATURE: (15 points, 5 pts. each) Give an acceptable IUPAC name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. aw— H . |\\‘\\\ 2. For each structure given, draw the important resonance contributors. Circle the major contributor. (14 pts.) 0 a- W e b. CH30\/\/ N(CH3)2 3. Place the following compounds in order of increasing boiling point. (1=lowest, 3=highest) (6 pts.) Aw M w E D D 4. Circle the compounds that can form hydrogen bonds in a pure state. (4 pts.) 0 0 o \ ll M NH C-OH CH3CH2 -C-H M F ——/ 2 D 5. Place the following compounds in order of increasing acidity. (1=least acidic, 3=most acidic) (6 pts.) 0 O H H CHaCHchzNHz CHgCHz-C-O-H CH30H2-c-NH2 D D E 6. Predict the products that would result from an acid/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.) (arrow) 0 ' Na + 7. For the molecule below determine th in the boxes provided. (10 pts. ) all in CHa—CEC e hybridizaton of the indicated atoms and place the answers 8. For the reactions below, provide curved arrows to in dicate the movements of electron pairs associated with bond breaking and bond forming, i.e., provide the mechanisms. (10 pts.) ‘3“3 ?“3 sto $“3 H °~ ?”3 _ _ 2 o H 0° aCHa Cl? Br -> orig—(In —> CHs—c—ofi —2—'> CHa—C-OH + Had I l CH3 CH3 CH3 H CH3 + Br' ,9. b. orig—0° 0°. + CHa—Br —> CHa—O—CHS + Br' 9. For the each of the followin large box. Place the cyclohex g substituted cyclohexanes, draw the more stable conformation in the (12 pts.) anes in order of increasing stability (1 =Ieast stable, 3=most stable). H3 -I||l|O 9H3 H3 -I|IIIO CH3CH2\\“ CHQCHa CHscHg CHQCHg CHSCH2\\\\.. [j E D "’"ICHQCH3 MOIYD 10. Draw all structural isomers and geometric isomers (cisltrans) resulting from theXbromination of ethylcyclopropane (structure A). Place geometric isomers next to each other and circle them. (11 pts.) ACHQCHg A 11. Consider the following reaction: (CH3)3CH + I2 a. Given the bond dissociation energies (BDE) below, calculate the overall AH° in the box provided. (4 pts.) ————’ 4—— (CH3)3CI + H1 b. Are the products or reactants favored at equilibrium? (2 pts.) Bond H -—X bonds and X --X bonds H—H D —D F—F C1—C1 Br—Br I—I H—F H—Cl H —Br H—I HO --H HO-—-OH Methyl bonds CH3 —H CH3 —F CH3 —Cl CH3 -Br CH3 —-1 CH3 —OH Bonds to primary carbons CH3CH2 —H CH3CH2—F CH3CH2_C1 CH3CH2—Br CH3CH2—I CH3CH2 “—OH CH3CH2CH2‘H CH3CH2CH2—F CH3CH2CH2—Cl CH3CH2CH2—Br CH3CH2CH2 “‘1 CH3CH2CHZ _OH Bond-Dissociation Energy kcal/mol 104 106 38 58 46 36 136 103 88 71 119 51 104» 109 i 84 70 56 91 98 107 81 68 53 91 98 107 81 68 53 91 Bond Bonds to secondary carbons , (CH3)2CH—H (CH3)2CH-—-F (CH3)2CH—Cl (CH3)2CH—Br (CH3)2CH-—I (CH3)2CH—OH Bonds to tertiary carbons (CH3)3C —H (CH3)3C —F (CH3)3C —Cl (CH3)3C _Br (CH3)3C —1 (CH3)3C _OH Other C -—H bonds PhCHz —H (benzylic) CH2=CHCH2 —-H (allylic) CH2=CH -—H (vinyl) Ph —H (aromatic) C —C bonds CH3 “CH3 CH3CH2 —CH3 CH3CH2 —-CH2CH3 (CH3)2CH ”—CH3 (CH3)3C —CH3 Bond-Dissociation Energy kcal/mol 95 106 I 80 68 53 91 91 1.06 79 65 50 91 85 87 108 110 88 85 82 84 81 ...
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