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Test_I_3331_I - mum “‘70 w aafl am I NOMENCLATURE(16...

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Unformatted text preview: mum “‘70 w aafl am I. NOMENCLATURE (16 pts; 4 pts each) Give the acceptable IUPAC name for each of the following compounds, or draw the structure that corresponds to the given name. Be sure to indicate the STEREOCHEMSTRY where appropriate. 1) 2CH2CH3 CH3CH HCHfiHgiHCHg HCCH3}a 3) _ ./ (.33 >\/E'\\r. <¥%Br / i L '11. raters (33 pts; 3 pts each) 1. Identify as some or isomer the reiationship between structure (I), and structures (H), (DI) and (IV) (Please circle the correct relationship): maCHCHzCHCHzCHs CHEeHCchacrrg ctr; “ECH . H3 -‘ Hg st “tr CH3€HCHCHQCH3 ' {ISH3CHCH2CHCH3 " :53.- CH3 'CH3 CH2CH3 J (m) (m 'a- (11) same, (IKE) isomer and (IV) same. 0) (11) same, (BI) isomer and. (IV) isomer. 'c) (E) isomer, (H1) same and (IV) isomer. 2‘ Rani-c the following compounds in order of decreasing acidity of the hydrogen of the CH3 group (most acidic. = 1, least = 3): /f' ‘i\ CH3-—CH—_=Ci-I-—CH:CH2 CHgfiHr—CH—flt’ 'CH3~CHg——CH__CH~,_. 1" ‘ :72- . _ 1 ‘_ it . . l I: I ' ! I . I 3. Rank the following compounds merrier-of decreasing boiiing point (highest = 1, lowest = 3): A . . 0cm - " fl H 1.; . 1/_ JOE LJ L__J 'J ' . - i , 'l I . - £5J¢¢\ _ l . 1 _ t __-_1 . L__f Lo I») .. —_ Wm WW .-.-v-—-W. _ __ m1. . “wax-9mg". mmimmfim mrmmflm Hit; 2% “‘“fifi-‘tflft-mfif" a‘fimfl-F‘Il'?‘i-a.-L'Ejjvtjlqufifl.,1:l 331?; a E I"? 1:?" -M ‘4‘? i. {3' NJ 4. Calculate the formal charges on the indicated atoms in the moiecules below: 3‘: 6: E — « CH3"— -—CH3 CHg—"t —~ EN: CH3—u \ .. (:é: Q: T Y 6. Indicate the state of hybridization for each of the indicated atom-s in the molecule below. The lone pairs of electrons are omitted. You must decide if they are present or not. ' ' I ' _ W TrTHCOCI-Ig Nam TwNw—Tff t1 ‘ ij—J U“: - I? .1..— r~ 7. Draw the Newfilm projection tor the conformation of 1,2-dibromoethzme (CHQBI—CHjBr) that has no net dipole moment: ' bJ 3. Given the bond dissociation energies (BEE) below, calculate the overall Alf-1° for the following reaction (please put your answer in the box): _. hv (CH3)3C-H ‘5' Bf: —'—"—+ (CH3)3C-Bl‘ + HBr Compound (BITE, kcal/mol‘a (CH3)3C-H 91 (CH3)3C-Br 65 Br-Br 46 H—Br . 88 CH3 ~Br 70 gig . ‘ .1 . 9. Indicate the direction of equilibrium for the following reactions. Place your answer in boxes provided. Ift'ne reaction is shifted towards (l) more product side, indicate -———* ' (2) more reactant side, indicate +———— 4—,—-—-_ ; and (3) if‘ooth reactants and products are present in near equal amounts, indicate -———-—r—. , "The acidity constants (pKa) are provided): a) (——\‘\__ - .'./m_\ ' , . . \ ,r, CH2COO + CHsCH2COOH : \\ /r-—CH2COO:I+ CHaCHfiIOO \:\ If} - \l—x’f _ (pka=4.9) (pka=3‘_8) _ _ 5) CHgoH + I. aOI-i ' “" I CH30N3+ + H20 Vi}. ' (plot-715 5) (pka=15,7} (pkg = 25) Lv. .i. u- wile-gs I‘d. w" "k—<:; tic-u. -.... . c-c' '.:\_'...'..‘. .\'.\ __--...._,.l_.\': '...| the resonance hybrid structure: NP NH; | . re 8} CH3CHf—Ig—“N—Hg +——+ Cia3CHf—C-z‘istg fiflflfiu Q ~ . Q9 C H l “'1 _ b) CHTC—NtCZHfi: H CHs’Hcl‘; (CH3): _ c- T G t C) CI—lg—owCE-‘N +~m~+ ChngZC:¥.1 i ' l H H 11. Circle the most stable confomer or structure in each of thc following pairs of compounds: ‘ H i: H H b) VS ‘ H l H H H F H (Imam): C) / VS J" / HY/ CH3\fr'l// . CH3 IEI L11 canfOrmationai Analysis: Total Points = 13 l. Use the table of strain energies given below to provide answers for parts a - c. -a. Construct a Newman projection about the 02—03 bond that represents the most stable eclipsed conformation of 2,3~dimethylbutane. Place your answer in the box provided. (3 pts‘) ; b. Construct a Newman projection about the'Cg-C3 bond that represents the most stable staggered conformation of 2,3-dimethylbutane. Place your answer in the box provided: (3 pts.) ' _fl_ i '0. Calculate the difference in energy between the Mo conformations provided in a and b. Show yourcalcuiation and theanswer in the box provided. (1 pt.) - strain energies: H, H eolipsing : t Real/moi Cate); H eclipsing : 1.8 koalfmoi ' CH3, CH3 gauche = 0.9 kcal/mol (H3, CH3 eclipsing : 3.0 kcalr‘mol Place-the fettowing substituted cyclohexanes in order of increasing stability (1-..- Ieast, 3 = most stabie). (6 pts.) mot-13):, grows gCHsta in e e . _ :1 r1 [1 ii. .Isomers; Total = "i 4 points raw structures of all of the dichlorinated products that may be produced in the free ldlcal halogenation of cyclohexane. (Please note: duplicate and incorrect structures 1“ He penalized.) CD _....__ . “W _ynafiégszotal Points = 6 PEJKE‘JLB ' . :batgitgpportant resonance contributors for the compound beiow and circle the major t : i . CH3 ”fajxéfiw’ffixéwilr, q Thermodyhamics/Kinetics: Totai = 18 points isider the conversion of A to D through Intermediates B and C and the data given: _._., B —.-——» C ———+D step 1 A ————a- 8 E3 = 15 «cal/moi, AH” :13 Real/moi step 2 B -———r C E3 = 10 kcai/moi, AH° = ~ 6 koai/moi step 3 C ——~+D Ea = 2 kcai/moi, AH" = - 20 kcai/moi Construct a reaction energy diagram for this reaction. Make sure to show how the en energies are consistent with your diagram. Label the positions of species A, B, and D, the position oi-the second transition state, and oieariy iabei aii Ea‘s and io‘s and the overaii AH° (approximate AGED-112 pts)‘ M a f WI” ”I: 1192 "P- -.-j-':_- ’“. it: r'n ,1“. Pin” r: w' .Which step is the rate determining step? (2 pts) I [I A ~ . ' i . Calculate the overaii AHC’ (approximate 25.60) of the reaction. {2 pie) r i Q .. u. the production oi product favored at equiiibrium? (2 pts) _ _ I f0 ...
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