Test_I_3331_C - First Exam Name (PRINT) Last, First...

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Unformatted text preview: First Exam Name (PRINT) Last, First Chemistry 3831 Signature Séptember 21, 2001 Ptease circle-the name of your professor and class time where appropriate. Dr. Bean (TIT h 10 AM) Dr. Cat Dr. Bean (TIT h 5:30 PM) Note: Present your student ID when you return the exam booklet 1. Draw the Lewis Structure for each compound. Include all nonbonding pairs of electrons and charges, if any. (6 pts) 21) NH4C1 b) KOC(CH3)3 c) CHasOECHE 2. Draw the line-angle structures of all products of monochlorination of memylcyclohexane. (Please note: duplicate and incorrect structures will be penalized). Place the stereoisomers (geometric isomers) next to each other and circle them. (11 pts) 3. Consider the following structure that only shows the connectiviw of atoms in the molecule: a} Write- down the state of hybridization for each of the 6 indicated atoms (6 pts). 13) Draw a geometrically correct representation of the structure, placing as many carbon atoms as possible in the plane of the paper. (Do not sketch orbitals) (2 pt) c) In your above drawing, the zit-orbital of the C=C bond should be i) in, ii) above, iii) below, or iv) both below and above the plane of the paper (circle one of the four choices). (1 pts) 4. Indicate the lone pair electrons, if any, and write down the formal charge on the indicated atoms in—the molecules below. (6 pts) - /CH3 “SOL /CH3 O Hec CH3 H T -—N \CH3 H~o 1/ W ‘ FSB/ 1 f I i 1 5 a) In the boxes, rank the following compounds in the order of decreasing acidity of the indicated hydrogen (#1 is the most acidic, and #3 the least acidic). (3 pts) \jfi 11/chI \/e\T DD E] b) In the boies; rank the following asses in the ordet'of increasing basicity (#1 has the lowest basicity, and #3 the highest basicity}. (3 pts) ' ' e 9 o CHsCHQO CH3NCH3 CH3 DEE c) In the boxes, rank the following anions in the order of increasing basicity (#1 has the lowest basicity, and #3 the highest basicity). (3 pts) 6) E) e D [I E El 3 6. Consi‘de‘r‘the‘reaction of propane with chlorine to form 2—chlor0pr0pane and HCL (a) Using the bond dissociation energy table at the back of the exam, calculate the AH“ for this reaction. Be sure to show your work. (4 pts) (b) Is the reaction exothermic or endothermic? (Circle one) (1 pts) (0) The second propagation step in this reaction involves the reaction of a secondary propyl radlcal with C12. Write an equation from this step using fish-hook arrows to Show electron movement and calculate the AH” for this step. (4 pts) _ 7. Please give an acceptable tUPAC name for each of the following compounds. (9 pts.) H Ema CH-?H-CHECH3 a. CH3 Elr H as ((-31. go; toe structures given, draw the important resonance contributors, and oiroto the major oontibutors. p s. / o a. + OH 0 O - 9. For the reactions below= provide curved arrows to indicate the movements of electron pairs associated with'bond breaking and bond forming, Let: provide the mechanisms. (7’ pts.) a_ :9—H + CHECHg—Br ~—-—-——+— CHsCHgn-OH + Br + .c b. :CHE + H—Br '——“—” + Br 58:— o ff :3:— I II I _ c. macaw2 + CH30\ - ————y CH30£H2~CHCH3 H 10. Indicate whether each molecule is polar (P) or nonpclar (N) by placing the appropriate letter in the box provided. (6 pts.) a. F— CEO—F b. cmmCHz C. PFs _D_ [3 ll 11. Place the following compounds in order of increasing melting point. {t = lowest, 3 :highest) (3 pts.) 12. Circle the compounds that can form hydrogen bonds when in a pure state. (4 pts.) (3 0 || (CHalsN CH3 -C-OH CH3-C-OCH3 o _ CchHg-O — CH3 CH3 _ 5_CH3 G H - 13. Conformational Analysis: a. Draw the more stable chair conformation of each of the substituted cyclohexane isomers. (6 pts.) CH3 CH3 gems I (Jr/C(CHm CH3 CH3 A B b. Which is the more stable isomer, A or B? (2 pts.) :1 c. Looking along the Cg - 03 bond, draw the most stable Newman projection representation of 2-bromo-3-methyibutane in the box provided. A table of strain energies is given below. (3 pts.) Strain Energies: H , H— -eelipsing-i-nteraction -=' 1 ;O"Kcallmoi H, CH eclipsing interaction = 1.3 Kcal/moi CH , H3 eciipsing interaction = 2.5 Kcal/moi H, r eclipsing interaction = 1.6 Kcallmol CH3, Br eclipsing interaction = 2.3 Kcai/mol CH3, CH3 gauche interaction = 0.9 Kcallmol CH3, Br gauche interaction = 0.7 Kcaifmol TABLE 4—2 Bend-Dissociation Energies for Hcmcly'tia Cleavage:- A:B —--> A- "r- -B Bond-Dimecz‘az‘tm Bond-Dissociaziusa Energy Energy 'Bom-z' kmva U/moi - -- - Bow! kcab’moi b21120! -. H-—K bonds and X—-?{ bonds Bonds to smonday cal‘brsns D—D :06 4-4—1- ECHfiCH—F 106 F—F 38 159 {Cl—33)XCH'- Cl ‘ so 335 CITCL 53 24-2 £CH3}2CH-—Br 63 235 Br—-B=: 46 292- (GHfiCI—E—I 53 22: I~—~I 36 151 (CI-Igflfl—OH 91 38': H“? 1-35 559 Bonds to ternary carbons H—Cl 103 431 {mEhC—H 91 331 H—Br 38 368 ($933194: 105 444 Hfll 71 293' (6.33);ch 79 331 - H0 —5 11.9 493 (may: ~13: es 2T2 HO—OH 51 213 [mzhc_1 50 339 may bands ' (CflghC—OH 91 33: CHE —H 104 43? 013510: C—H bonds CH3 “F 109 45° PhCH;-H (bcnzylicj as 355 CHr-Cl 84 351 CH2==CHCH2—-H (aflyljc) 37 364 CHEWBI 70 293 CizgmflH (vinyl) 108 452 Gift-I 56- 334 PhH-H {aromatic} 110 460 {133.0}? _ 91 381 C —-C bands Bonds to pumnry cal-cons CHE—4:};a 35 353 CHECE‘IQ—ii 98 410 maCHz‘CH: 5 355 CHJCI-Ir-I' \ 4'48 Cflgflfi—CHZCH, Samara ’ 31 3‘39 {mahfl'l‘C’l—L 34 351 CECE"? #38 285 (make—1:541 ' 31 339 CECE—~01! 91 381i CH;C§I¢CH1"*H _ - I mamzcaz ——1= :07 443 2—CHCH2‘BT [allth 3‘) 35 CI-I3Gfimg—Cfl 81 339 Cchl'Izcflgmfir -. 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This note was uploaded on 04/24/2010 for the course CHEM 3331 taught by Professor Bean during the Fall '08 term at University of Houston.

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Test_I_3331_C - First Exam Name (PRINT) Last, First...

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