Exam1 - {Qt/42f PRINT NAME 1. ‘ The number of hybrid...

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Unformatted text preview: {Qt/42f PRINT NAME 1. ‘ The number of hybrid orbitals in the molecule ‘ - is A. 15 16 C. 17 D. 14 E. 19 2. Which of the following molecules will have a molecular dipole moment? CFzBI‘Z H2C=CF2 CBI’4 A. None of the compounds have a dipole moment. B. All of them have a dipolemoment. C. Only two of them have a dipole moment D. Only three of them have a dipole moment ® Only four of them have a dipole moment 3. The F—B—F bond angle in BF4 9 is A. 180° . 1200 (El 1090 D. 104,0 E. 900 307/315 EXAM I DRAFT FALL 2010 1 my PRINT NAME 4. The correct order of the following compounds by boiling (lowest boiling point first) (1) pentane; (2) l-chloropentane (3) pentyl alcohol; (4) neopentane, (5) isopentane is A. l, 2, 3. 4. 5 4, 5, l, 2, 3 C. 5, 4, 2, l, 3 D. ‘4, 1, 2, 5, 3 E. none of t e other four choices is correct 5. What color is your exam? A. White B. Pink C. Blue D. Yellow 307/315 EXAM I DRAFT FALL 2010 2 Mtg/K7 / PRINT NAME 1X. (10 points) ‘ A. Draw the structure and give the IUPAC name of an isomer of C7H16 that fits each of the following descriptions. _ a. Has only two methyl groups avg/(LOW b. Has more than two methyl groups and no 30 hydrogens c. Has a two carbon branch attached to its main chain Cutglécraflcagwfi mm at gfiAILQCQk/g') fag b. Nam :, , f c. Name: [74%, W l , fiat: new; we s C J . 2’ Lucgil 172ka m i \ “I; ‘ “r I ’ ‘ , m «w, n 5‘”. ,. Jx K, 55 a amp WW W52; (Cl 3* “a it, a (get flew"; 5c“; garter-J? 1:; 4,4 éfidmdk , flaw, W W. i W A u, ‘3 0% B. Draw the structures and name all the primary monochlorides that can be formed from reaction of (CH3)3CCH(CH3)2 with C12 and light. (Use only as many boxes as you need) 01+ , 3 cr-cm‘caeéceg L 307/315 EXAM I DRAFT FALL 2010 3 M7 PRINT NAME I a: (10points) 2.2,: >1 3 Viflcmga, (Z! by, :3” A. Draw the structures and name all the primary monobromides that can be formed from reaction of (CH3)3CCH(CH3)2 with Br; and light. (Use only as many boxes as you need) a. Name: b. Name: a. Name: b. Name: ' B. Draw the structure and give the IUPAC name of an isomer of C7H16 that fits each of the following descriptions. a. Has more than two methyl groups and no 30 Hydrogens b. Has a two carbon branch attached to its main chain 0. Has only two methyl groups a. Name: b. Name: c. Name: 307/315 EXAM I DRAFT FALL 2010 4 t PRINT NAME 2X. (12 points) A. Draw two other contributing structures for the species u-e W O that are more important than this one. Circle the better of the two. HN A flex flew-e» L 3) pm my” ‘ ‘ E? a Wt B. Draw two isomers of the composition CH3NO in which each atom has the preferred number of bonds in its most important contributing structure. Show all lone pairs and all bonds. i” C. Give the name of a dichlorocyclobutane that has 1‘ ' ’ no dipole moment. i \ IQ :1 M m H cfihfip‘mfl +mfi‘éfl/‘S "aw éfi MA. Q L Lg ll Q I‘ v. 307/315 EXAM 1 DRAFT FALL 2010 PRINT NAME ZY- (12 points) Sfiyfi A. Give the name of a dibromocyclobutane that has no dipole moment. B. Draw two isomers of the composition CH3NO in which each atom has the preferred number of bonds in its most important contributing structure. Show all lone pairs and all bonds. C. Draw two other contributing structures for the species o\l "e H that are more important than this one. Circle the better of the two. 307/315 EXAM I DRAFT V FALL 2010 6 'PRINT NAME 3X. (14‘points) A. Monochlorination of cis—l ,2—di1nethylcylobutane produces four different products. Draw their structures using dashed line/wedge projections to show stereochemistry. 4‘ 2‘ 2A 1 .41, 7- r \ g, r. B. Given that the relative reactivities of hydrogens in chlorination at certain I conditions are 3°: 20‘: l0 = 6 : 5_:l calculate the relative percent yields (to 2 significant figures) of each of the four products that can form from monochlorination of isopentane ( V ) Put your calculated relative percent yield next to each product. Work must be shown for credit. No guessing. {Mex g g; x R g :53 ‘5“ £3 ’ j,” :3) “@337” " ‘7 a} fins»? 3 , cw a rm a ‘“ ,. W (64% p m w 6 9 A ’4. n 52/ v‘ ymma 30 , f4” 20 -,* ’ “a; 10 [4 A?) 10 6,. / 1/ 0 Wu —-—-—" ”" “" " ————-’ “” —-——’ ’if g ‘ .. 3 x4, 5 A if”)? m WM” 4% W5? ‘5” mi V "" W 3% S ’ W Wit/é z " M with JV: 0 I, I ‘ mJ/ pt] {b If» I" at 1% tea!» 2r (ML ( 0 307/315 EXAM 1 DRAFT FALL 2010 7 4M PRINT NAME 3Y; (14 points) A. Monochlorination of cis-l ,3—dimethylcylobutane @ / *fiflgmwwmwg%%% “142.0ijfi produces four different products. Draw their structures using dashed line/wedge projections to show stereochernistry. 3299' r 7» 'B. Given that the relative reactivities of hydro gens in chlorination at certain conditions are 30: 20: l0 = 7 : 4 : 1 calculate the relative percent yields (to 2 significant figures) of each of the four products that can form from monochlorination of isopentane ( ) Put your calculated relative percent yield next to each product. Work must be shown for credit. No guessing. (7" l '11, 3Hs3 lx‘f : y W l<7£7 10 11.5% 1° l>/% 7@% 3%? 7“! %w 307/315 EXAM I DRAFT FALL 2010 8 4X. V65 ? PRINT NAME (10 points) A. Draw the more stable chair conformer of trans—l—ethyl—Z— methylcyclohexane using the template given below. Fill in only the alkyl substituents. We" , L B. Draw the more stable chair conformer of cis-l—ethyl—Z—methylcyclohexane using the template given below. Fill in only the alkyl substituents . . fl} WV C. Draw the more stable chair conformer of trans-1~ethyl-3-methylcyclohexane using the template given below. Fill in only the alkyl substituents Ma Lt” D. Draw the more stable chair conformer of 6119-1 ~ethyl—3 ~1nethylcyclohexane using the template given below. Fill in only the alkyl substituents Er“ NEW. ‘ ‘ E. Draw the least stable chair conformer of all the ethylmethylcyclohexanes using the template given below. Fill in only the alkyl substituents Fla, Wfifi 307/315 EXAM I DRAFT FALL 2010 9 gRINT NAME 4Y. (10 points) A. Draw the more stable chair conformer of trans—1—1nethyl—3— propylcyclohexane using the template given below. Fill in only the alkyl substituents ~ as B. Draw the more stable chair conformer of cis—l~1nethyl—3—propylcyclohexane using the template given below. Fill in only the alkyl substituents ~ as C. Draw the more stable chair conformer of trans—1—methyl—2~propylcyclohexane using the template given below. Fill in only the alkyl substituents. » at D. Draw the more stable chair conformer of cis—l-methyl-2~propy1cyclohexane using the template given below. Fill in only the alkyl substituents W E. Draw the least stable chair conformer of all the methylpropyleyclohexanes using the template given below. Fill in only the alkyl substituents W 307/315 EXAM 1 DRAFT FALL 2010 10 M PRINT NAME 5X. (12 points) Draw six of the eight compounds with the formula C5H10 that do not have cis— trans isomers. (Hint: 4 of these structures have a ring) fm 41% 85.0% W) $091,“. CM/ «f- "tr" 5w,” (.2 if“ 307/315 EXAM I DRAFT FALL 2010 11 MINT NAME 5Y. (12 points) Draw six of the eight compounds with the formula C5H10 that do not have cis~ trans isomers. (Hint: 4 of these structures do not have a ring) ngEE SE SE 307/315 EXAM I DRAFT . FALL 2010 12 ’ PRINT NAME 6X (14 points) A.Draw the skeletal structure of each compound whose name is given below (a) diisopropyl ether F94 (b) neopentyl alcohol r713! ‘ E V (c) sec—butyldimethylamine / / “V? W m f \ (d) tert—butylbromide ; “la/é, - (e) bicyclo [3.3 .O]octane CD (f) 4,4—di—(3-ethylcyclobufyl)—3—methylheptane «kl/Z» “307/315 EXAM I DRAFT FALL 2010 13 PRINT NAME B. Using the templates below (Newman Projections) draw three different staggered conformations of 1.2—dichloropropane. Make C—l the front carbon of your projections. Circle the most stable one and underline the least stable one. (END Q g t T M H" C. Given that the energy difference between the two staggered conformations of l—chloropropane is 1.1 kJ/mol and that the energy difference between the two staggered conformations of 1,2—dichloroethane is 0.3 kJ/mol, calculate the energy difference between the least stable and most stable conformation in Part B. J? 91¢ "" i W AL 5’ eh. [ titre?! 6’ Gil/Lam 5‘ Or?) é”) film, I’m t W at M, [g flvl’ f a) t J /fls¢e~cfi '. (7 manta“ ' , . , , [4w -. marl; E“ p ‘f flflm‘flfli . i Ciel—(1M? M»- A It” 9* , ftp » a, ‘ u . ‘ gfi/cxpfl/Q m if tit V “2 Q i 3; 5"" If 9/; 307/315 EXAM I DRAFT FALL 2010 14 jig/£12” P R‘INT NAME 6Y. V (14 points) A. Draw the skeletal structure of each compound whose name is given below MD + I 307/315 EXAM 1 DRAFT FALL 2010 (a) di—sec-butyl ether "\mg / J1 4* (b) neopentyl chlofide Cl (C) isopropyldimethylanfine f >m$ (d) tefi—butyl alcohol {fame fi' (6) bicyclo [3.2.0]heptane (f) 4,4—di—(3~methylcyclobutyl)-2—1nethylheptane 15 PRINT NAME B. Using the templates below (Newman Projections) draw three different staggered conformations of 1.2—dibromopropane. Make C—l the front carbon of your projections. Circle the most stable one and underline the least stable one. C. Given that the energy difference between the two staggered conformations of 1—bromopropane is 1.4 kJ/mol, that the energy difference between the two staggered conformations of 1,2—dibromoethane is 0.4 kJ/mol, calculate the energy difference between the least stable and most stable conformation in Part B Avast/pd (Fr/WM fiawthb :. Ora/ATM iz.‘e)+ ,4 W»?r2 Cg/cwuct’v? a o/coAj’lgww/(f . bLC/‘NQ‘: ‘ was?" LW‘Q Aflfi ivgrm'r ‘1“: I" ‘1‘” 307/315 EXAM I DRAFT I FALL 2010 16 PRINT NAME 7Y. (12 points) A. Write the propagation steps for the reaction of C12 with propane to form isopropyl chloride (2—chloropropane), . x Cu»: 6% + g (31.. ———-a (324/3 my CH3 + {+C/ +2. 4 ‘ "‘9 c a 4, 1, a 50/4 0/3 +0.3; Gag fatal: 1‘C/ ‘1! B. Using the following bond energy data, calculate the AH" of each propagation step and of the overall reaction. Bond DH ° (kJ/mol) Cl—Cl 241 C—Cl 355 { H—Cl 429 t Propyl—H 425 Isopropyl—H 414 A Mtg/JV L, GO 372 W” 4 , A c] +1 Step1 [1054— 4/17 : aim/W \ W _ I ~ gig/(WW‘E‘PLStepZ Q-V/‘o 553 2‘ ’ I’VUM m r W ~34 Overall " I L? A} W C. Using the bond energy data given above, calculate AH" for the chlorination of propane to form l—chloropropane. lqfi)‘<flz_§'r3§f> :; wlfig’M’M D. In ten words or fewer (only the first ten words will be read) explain why the formation of one of one of these products is more favorable thermodynamically than the other. Be I very specific in your answer. VA C” W) i 5 ' (£79 £1] 17% a W W W?! math; 307/315 EXAM I DRAFT FALL 2010 18 KIM ! PRINT NAME 7X. (12 points) A. Write the propagation steps for the reaction of Br; with propane to form propyl bromide (l —bromopropane), +2, Q‘Gpch‘scflgxrlg’“ ~“3 what/Z/Ué' +HZ/L , 9% @4c; 4 ' 4%» Cfiécééyrlfi f L ’7 (3 {fimél‘m +72 B. Using the following bond energy data, calculate the AH" of each propagation step and of the overall reaction. Bond DH ° (kJ/mol) Br—Br 194 ] C—Br 294 l H—Br 362‘ Propyl—H 425 Isopropyl-H 414 LC—C 372 ' «ist- 1 Step 1 rah/5:“ 3"; 3“ é’g .1} M W ‘11 Step2 M; 400437 /'l all PH Overall WM 3" - 7 batofiqu/ W C. Using the bond energy data given above, calculate AH“ for the bromination of propane l to form 2—bromopropane. 1’ L, WV?“ L/fl/l~<3€2+ 2,99) 2 -— 43U7W€ D. In ten words or fewer (only the first ten words will be read) explain why the formation of one of these products is more favorable thermodynamically than the other. Be very specific in your answer. j] Bogfop93Q C’H A w-QQLW aLKhagml/Cwflt 4 J 3% 307/315 EXAM I DRAFT FALL 2010 17 ...
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This note was uploaded on 02/12/2012 for the course PSYCHOLOGY 101 taught by Professor Michaelleyton during the Spring '08 term at Rutgers.

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Exam1 - {Qt/42f PRINT NAME 1. ‘ The number of hybrid...

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