Test_I_3331_G - Kev Hm; an g INF?” ONE-fl First Hourly...

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Unformatted text preview: Kev Hm; an g INF?” ONE-fl First Hourly Exam - Dr. T. Albright 617l02 name - please print Note: A Periodic Table and a table of bond dissociation energies is on the last page. You may tear it off to use it. I. (35 pts.) Name thefollowing compounds using lUPAC rules: Ha'c ‘ CHa—iefifECHz “IECIIJHT‘IIIIHLCHg—CHQ _ HaC u ‘ C L}. (_ 'C'.,l‘.:'\._c v» l I: -5 -' . - .l J ':' -' . é. -- 5' .o /.:3 - / ._r' MM: 2. (I 5 pts.) Draw a Lewis structure including all nonbonding electron pairs for the molecule: NCCHzCOCHzCHO 3. (I 5 pts.) In the foliowing reaction labe! each reactant as an electmphile or nucleophile and show by means of curved arrow(s) the movement of electrons. 4- gal A .. g9 HST- CHg—E—‘éHs -' + O- | + / \ / \ /+\H CH3 H H CH3 CH3 H K3 ,, - ':= .--.i :5 t-‘r‘c—I.c.ésw=-€° '- 4. (I5 pts.) Circle the compound which has less ring strain. Give tW-O different reasons (just one short sentence for each reason} for this. ...-F"~'?!.“-:‘v.~'—'<=‘1'-'-‘-'r_'>5'—;;i.-L:_ .. . ..«- I” With. D versus % I “ r" / ‘Lj'. ma- we Q—LPLL (I... a» 2 ~ , , S. (10 pts.) Rank the following in order of decreasing bascity: ,1 in, IUNH3 CH3COOH CH3COO‘ NaOH NH2' "’ compd: A f,” B C D E Bascity: > i > (greatest) . (smallest) 6. (I0 pts.) Rank‘order the stability of the radicals shown below using the table of bond dissociation energies on the last page of the exam: H30 l- ‘ -CH3 CH2==CH- CH2=CH—éH2 orig—(:2- . H3C compd: A B C D E Stability: > > > S (greatESt) (smallest) Exam #1: CHEM 3331 A1. Nomenclature (3 pts apiece): Give the IUPAC name for each of the following compounds. 1. (CHg)2CHCH(CH3)CH2CH(CH2CH3)2 H 2, CHZCligfL-H a, t \l X l I CH(CH3)CHECH3 2. 3. A2. Nomenclature (3 pts apiece): Write out the structural formula corresponding to each of the following IUPAC names. _ — u. If ‘ C “- LI. 1. 4—(l—chloroethyl)~3,3-dimethylheptane g; z; 24:32: u l; ;__- r, 9, fl C g? 2. 4-isobutyl-1,1-dimethylcyclohexane "" "“___ 2+ 6. a .- B. Facts (Draw in all missing lone pairs) 1. In the following species, specify the formal charge on each indicated atom (8 pts). Jl-r’ ‘_ a. N =' ?; 0 == ? OWN-—Q'- F—w—IT—F b. 899:? 'F; 2. Inorganic molecules can possess conformational mobility (i.e., they contain rotatable single bonds) just like organic molecules. Please draw two different planar conformational structures of hydrogen peroxide (HUGH). (Hint: In both structures, all four atoms should lie in the same plane; think about which bond you should rotate)- (4 pts) “gra- . Determine an acceptable Lewis dot structure for CH303N. _ Show all lone pairs of electrons. (Hint: One oxygen is betWeen carbon and nitrogen). (5 pts) . Determine the hybridization of each indicated atom. Draw in any missing lone pairs. {4 pts) ,--,—o CH . \+ 43 c duff/j \T H. . Order the following hydrocarbon compounds in order of increasing boiling points (i.e., 1 = lowest b.p., 3 = highest -b.p.). (3 pts) 9M0 . Answer yes or no to the following questions regarding the isomeric relationship of the following pairs of compounds. (6 pts) 3. CH3CH2CH(CH3)CH2CH3 VS. CH3CH(CH3)CH2CH2CH3 Constitutional isomers? Stereoisomens? ; r; Cl “3 b. Bf vs. BF Conformational ismners? Stereoisomers? OCH3 H ' H H Conformational isomers? Stereoisomers‘? 7a. Write the conjugate base (including charge) of the following compounds. (4 pts) Compounds pk I Conjugate Boar W— CHsCHzofi — HCN _ 7b. Arrange the compounds in 7a in order of increasing acidity. (2 pts) C. Conformation problem I. (12 pts) Consider the following interaction energies (kcal/rnol): H,H eclipsing = 1.0; H,C}-I3 eclipsing =~ 1.4; CH3,CH3 eclipsing = 2.5; CH3,CH3 gauche I 0.9; H,Br eclipsing = 1.6; .CH3,Br eclipsing = 2.3; .CH3,Br gauche = 0.7 To answer the following questions, construct Newman projections representing rotational conformations about fire C2-C3 bond of 2-bromo-3—methylbutane. a. Show your calculation of the total strain energy of the most stable eclipsed conformation. Draw the corresponding Newman projection. (6 pts) - b. Show your calculation of the total strain energy of the least stable Ego-ed conformation Draw the corresponding Newman projection. (6 pts) D. Conformational problem II. (10 pts) 3. Draw both chair conformations of m—l~terI—butyl~4—ethylcyclohexanc. Circle the more stable conformation. Briefly explain why your choice is the more stable isomer. (4 pts) 1). Draw both chair conformations of gig—1—tert—butyl-4-ethylcyclohexane. Circle the more stable conformation. Briefly explain why your choice is the more stable isomer. (4 pts) c. Which is the more stable isomer, 315— or m1—tert~bntyl-ethylcyclohexane? Briefly explain why your choice is the more stable isomer. (2 pts) E. Identify the hybridization of the carbon and oxygen atoms in the following structure. Draw the three-dimensional bonding orbital picture of fire. following structure. Draw all lone pairs. (12 136) H Hztzzc—om—CH3 F. Monochlorination of the following compound (Cal-124) gave a mimre of monoohloroadducts that had a formula of C12H23Cl. Please draw out all of the monochloro— isomers in the chair conformation. Please ignore conformational isomers. (15 pts) ...
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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_G - Kev Hm; an g INF?” ONE-fl First Hourly...

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