Exam2-2-1 - i’ I i | I i E Chemistry 3223 32521 ~2~...

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Unformatted text preview: i’ I i | I i E § Chemistry 3223 / 32521 ~2~ Name W W Exam N0. 2 (1) (15} (A) (10) For {the acidwbase reactions beiow, suppiy the missing structures Within the boxes according to {he descriptive terms beiow the bexes (See information in the Appen ndix as .. ‘vwwfl‘fl (i) CH3CM2<>1~1 + £11.- conju gate acid 1:01:13 11 gate base (11) C1~23c31§cz~12 1: Hp W mfg-1mg .1 1 11,-1.1 1 1:111 1111 (111.) CH3C§C~H + Name m (20:13" agate acid conjugal te base '51 (iv) {3113(3112131211112 + conjugate acid conjugate base elm-«"3“- ii" I v CI---E3CH OCHICHH + 3133 “WW 5 ( ) 2" [I a .. 1 CIi3CI€ZOC§--12Cfig fan-«’5; Féwfi. 1.6411335. 2311.331 (,9 1 (B) (3 ) For equations (ii) and (v), ‘5th all the bonding changes using {The curved arrow formafism “72th the simctures beiow Acid nonbondmg eiectron pairs to the structures as needed for the curveci armw formaiism M __ <9] 65 ___ C1--£3CHC§.~13 1 .17 _____ . ...._\‘& 31:3! (11) CH 1:11 CH2 '1' *H‘E; -;.h,_ 1 1g- -» 1 ‘1‘“: fig (1') C33CH2QCH2CH3 1 “1113123 1.1mm. C1--13c:112%c112c113 (C) (2) In equation (v) above, the nucleophile 1s 1 it 111 {.11 11.1.1111 and the eiectrophile is I}; t” *3; Chemistry 322a / 325a ~3~ Namemmm ,,,,,,,, W Exam N0. 2 (2) {29) (A) (15) I‘mvide IUPAC approved names for the structures, or yrevide structures inside the boxes for the names, as requested. beiow. . . ._ 01“.? i' E .i ‘Lf ‘3' k: ; \ a 5 ,__ 3. CH3CH'2CEHCHQC;I‘ZCN3 _ CHSqHCHZC‘EHCI-ig CH3 (31—13 . CH2c2-._--_13 " ' 515’ ‘3'- "th1"1“-'“':1 11% 23mm. :1: ii. “11/: iv} «~11 1:12:95“; *' e"; C- 1 i {i 22*- ? -"3'.;‘*.?5\ 1. ceecezémecemcm {1 ' ".5 ) ' E 51.3»? €331 EUAW‘IC Beyentenawoé (E) (5) For each of the constitutionai isomers of Gigs in the box beiow, indicate the number of different groups of equivalent H. Exampie using yropane: CH3CH2CH3 2 $1713 “III-t? I ~‘ I C [‘23 I: I . 1k .. . _ > “77; ‘1 _ EES-{meéflfiws W czeiacr‘récwgcrzzcyzgces 573‘ (makccfizmuizmla Z“.- CHsCHzgi'ifiaCHs 4” C1~13CI~I2C}I2C1&2C1{2CH2CH3 ’5? ' (22-13 ' - ' ' CH3 Chemistry 322af3253 —4~ Namew Exam No. 2 (3} (10) (A) (5) Seiect 3}} {he reagents from the list of Choices that wiil accomplish each chemical transformation beiow. Place your answers inside the boxes. -." " t. w, - 4*- M“ “a: w . 2;)“;- ;¢_' . H ; fl --"t;-\" ’M. i a 1: hr. <31~13CZ---12CEC—}-~£ ............................. a, CM3{;}-12c§c§; New '. in w s; as "‘1'; a? :i. a; a . GREGG} 'iNe-‘ifirefhan-ei“ N2? NH; in quuici NH3 - s’» ”l "J‘,‘jfjl‘j.§\ _ .3 . Choices: in m 3'1: . e .. (I CirigEijéyvtNa-methenol Nazi-"1 in diethyl ether Neg AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA a» Na“ 1511-12 «2: choices: Naeni—dndi.ethyi~ether“" eg-zgceeeeme‘mmmm mac-1W '2_ - "“‘W'a'emfhwei' acmcfig: My inhexane (B) (5) You have a mixture of two organic compounds, 4~methylphem3i and cyciohexenoi. Both are low melting soiids with very iimited solubility in water (less than. 3 g per ".108 mL). However, they have very different acidities as shown beiow. H OH pKa : 10.2 pKaz 18 mi: 35-5” C mp 24° c Cfig 4~methylphenol cyclohexanoi You prepare affirflgngbasxc, aqueous soiution of NaOH in water. When you add the mixture of 4~methy1phenoi and cyciohexenoi to this basic soiutioxz and stir briskly, one of the compounds dissolves compietely. (A) (2) Which compound dissolves? ‘ % ”'“i’i-féi-f :33? iii-1' '~-"-~' i (B) (3) Write a chemicei equafion inside the box that describes the chemicai change that resui’cs in one compound dissolving. 2 3 1 i ! Chemistry 3223/32561 ~5~ Na mow Exam N0. 2 (4) (20) Circie the cerrect answer for the fofiowing statements or questions. (A) Which of the foiiowing is mffiwgfgmififigifli? gig. if: it ______ circie answer __ - H303; AICIQ, NHL; 896.12 5" (B) Zhe order of acid strengths (strongest to weakest) for the compounds below rs ' circie answer czmiacfich-Imcm CI--13CI-.I.2CH2CHZOH CRflI-ifiOOI-I I>I£>IIZ ZZ>Z>§II 1 31 III : II>III>I (C) The order of base strengths (strongest to weakest) for the foliowing anions is ' circle answer . _ ' ' '- 13:33 it N112 C1130 - I. c313, 1mm?“ _ 11 I I; :1 :11 IV‘ W“ """" stat; in: ‘t ~11- IV>II>I>IILLLL1 §$W3W (D) Which of the acid; beiow wifl have the weakesgconjugate base? 1‘ if 3:- ‘ . I} circle compound 331-330“! WW... ...... $0! / {Lia-S C igCCOOM CH3COGN CICHZCOOH CIZCHCOOM pK mOéé / pKa 4.75 pj£<a : 2.81 pKa m 1.29 {L ) Which of the foiiowirtg IS the sttongest acid? ___ c1r1EI§W<ompound below '\ / + -- Er \._ q) H * C "t“ 1 -. ,L . pKa 11:25.7 pKa m “2 pKa 2 "3.8 pKa : “ELL/r WM.“ (F) The standard free energy changes (AG6) for the dissociation of two acids, PIX and HY, are given beéow. (})H~X 4— 1-120 m H3O+ + X' 13602435 Lotti/moi (2) HMYL + 1.120 W H30"? + Y‘ AG“ 2: 41.5 karat/mo} Accox‘dmg to these vaiues, ”k“ g" " F1 ‘3 E N) E """ {C' troio answer below) ~t11ode1dity~coz1§tantsém both acids are" greater that 1;] but {tin-X IS the: strHor-rgeru "acid; ~thc acidity constants for both acids are 1953 than 1 but 1-1 X 15 the Strongcr ac id { thé acrdity constant for II Y is greater than 1 and it is the stron gér étciEi Whiié thé acuilty conflam Nfiorm H— X as less than 1. and it ___is the weaker acid ~the‘ acidity constant for I-I- X rs greater than 1 and it is the stronger acid white the acidity constant for H Y rs 1855 than 1 and it is the weaker acid. Chemistry 32221/32531 ~é~ Name Exam No. 2 {4) Cents? (G) The {e} flowing diatomic molecuies thafigdre infrared active" are NmN 13:43: L2 II 1—1 (circleanswer) Nzandi-ii WenIy III N2, Brz and III only BIZ EHHM- / (H) The heats of combustion of severai isomers of C 6H1 4 are shown below According to these values, I:IISICJIZCHZCIIZCI-~12<:II3 {<2.I~I3),s<i<:_IIZCII3 CI'MF‘EQHCHs ‘ I‘“ CZ'IgCZ'ig AI“Igom.13 ~995mkca1/mei -991 5 Real X1210 993 kcal Arno} E” I; "y: P fl: i’ 3%" 5- {Ii IBM-"AJ- *ut, {circie correct answer beiow) ~2,2-dime£hyibutarle is the Zeast stabie and hexane is the most stehie isomer. HAS dimeihyibutane is most stab1e and hexane is the Ieast stabie isomer (J) A gasoiine with a performanpe in the internai combustion. engine equivaEent to a mixture of 80% ”isooct-ane" and 20% .he'pfgane is given an octane rating of {circIeanswe-r} 20 60 @3180 _. concise? The as j a3, r. a - Chemistry 3223/32531 -7~ 31;, _ Nameflmmm Exam No 2 p {L :. i : 9 K3 m 1.0 x 10‘29 (a CHBCCB3 4» H20 "W H30" + emcee—Z" ace’éone Ka <10*53 __ fl _ . CH3CH2CH3 + H20 propane {31am} '2 . ".5 =J'='-.:- 51‘? he? Fla (A) (10) Compiete the free energy diagrams below for the two equiiibria above by _ (3.) identifying the reactant and products states for Diagrams A and B by writing RS or 135 inside V {he cizcie .next to the Skate, (ii) drawng an arrow from the reactant siate to the product stare and 1,,” -' writing the symbol for the staodard Gibbs free energy charge (you do not need to cakuEate the value), and (iii) providing the correct structures for the reactarr? anti product siates for each M... diagram inside the boxes below or above each state. 1 A B free energy M— (13) (5) Use resonance theory to oxpiajra the. difference in. acidity bah/Veer} acetone and propane. Jae resonarr e structures in your expianation and refer to your free energy diagram above. Be Jr \» ' V J_ ’ ..... _ I l \ ‘i-Cfifs'fiifgsaa’. 1'“? {q {EW'k-Mi. 1115;”) % 1“€§'fi%rfi.—m m: 3:} RN?” :5, 1‘39": 3 _ ‘1: it; 41‘} {(3%)} ("ti x¥iil~ifl L;{.¥L 1: "1““ k1} L34?“ gwfim“? ‘3 £91.: id, Li»; the I“; ii“ [WE h } .. .. .7: - .- .. f- " - \ fly 2- _ {w __ _ . _ l- ‘ _ - _ -- -: 3'. 5.: L" L13“ :11: a 1 ""'C""~IEL«.’.'*§'="‘L "Z gun. {AL-f3“ L“: Rwy-"'12: (I; [liga- 3.3.45 ,, "E“iag (cg. 41 \N 1:}, 9‘}: wk?) ELH'!_ {La-1' Viv-ML ITE--Lp.--§_i"_ ( =,_ E». ;‘V \m, 1...}34. {1‘33 55‘ i": (”t 3(1) { I'm, a a _} \ ': g; i . ’ . ”5;” g I‘ is g E I" ‘ r 1‘1"“ " ’? h ‘1. I}\€.\..£.5{r“';—.’ 1‘ ggr é ' ’3’": ’1 "' pm i 3 {m . = I g f: !_ _ I { g e g “‘1' 1 i K ‘ r i “ 1‘ if” ‘ a 9 M; r 1,0 M a a Chemistry 322a /325a -8- Nameflmmw ............. Exam No. 2 (6) (1.8) Answer the fotiowirtg questions about the. conformations of simpte alkanes. (A) (2) Define “torsionai strain“ using ethane as an example. “ titrzamj at» {F} at». itemiw t-e'v.a't;."a ulna: »H it New { '5' «t: «m tog-- ”won't 5.5 1o tam? -t1,5,.~.-. Let-em one. «gee. 1.: 5555555.; M _ ‘ 5 it I you: 5 at t I 2, ,5. _ \_ _ J m \ ', .5; A... tum) m 5%“ ( (315.5“..b. ; 3‘ in”. is. i i.) 3‘ 5H )5?» a -' ' ‘5 .3 it; 121E": “opts; \ ”9r *5 ,.‘_"{5‘.: _ 3 f g } ' «fay «3/ ”‘3‘“ .,_ E r, (if; (B) (2) For the alkane beiow, identify the carbonmarborr bond with the highest barrier to .15 a]: _' rotation. Flace your answer on the tine as Cm»Cn where m and rt are the positionat numbers. a“ it 2 3 4 5: {5 *1 CH3~§H-CH2~CI--t:5 " ’6 t CH?) CAC with highest barrier to rotation 5 (C) (4) Draw gauche and anti conformations for rotation around the C2433 bond in butane (Crt3CH2CZ-ZZCH3} by compteting the appropriate Newman {Jrojectiort formufas heiow. Write the name of the conformation (gauche or anti) betow the compieted Newman projection formuia. Use ordy two of the tour Newman projection formulas betowr 5 5 f K “'3 H g 5"}: . . ”EL J 5 \ / f I‘ a a5 t1 ‘- a ”\‘I at a {-1 c o 1} / 5 \ M. t“ A mt i Samar ”a 4;; (ID) (2) Which conformation, gauche or anti, is more stabie? What is source of the energy difference between the conformations? “ f fl tit?” Wm a ma ‘H {‘3 we a Rita; at» rim-.4? \1 Ht: *3 V6 t Cate} ‘fa wk “>1 o «1:? a ‘ , r. Chemistry 322af325a ~9~ Name Exam No. ’2, (i7) (10) I am a hydrocarbon named A. My inflated spectrum is Shown beiow. Zreact with hydrogen gas over a piatizmm catalyst to give compeund 8 (IR spectrum below). Compoand B has a symetzica} structure with oniy primary and secondary H. Combustion of one mole of compound B gives 6 moles of C02 and 7 moies of H20. Provide detaiied structures for me (compound A) and compound 13 in the boxes below. Pt @y/ammam compound A compound B.— combustion- of- one mole of 15 no tertiary H 6 C02 4— 7 1"le .Q’ its a: 35.33;"; PHI! g 1-4:. wavenumber, cm” fiémoaeea 3990 2500 2000 1500240013001200 use me 900 see me --_ Y "i t l N80 1.: . I ' - . II 1- I ' - l E 53 w . , kg.‘ * m __ Wmi ‘ .u, _ 20 m m .- . m ‘3 I f - F 5 t E 02 ._.. a 5 5 7 a 9 1e :1 f2 13 " ' fa i5 Wavenumber. cm" 3600 3290 2800 24100 2838 1808 1600 wag":£:==-"“*= .' 4008 M00 1200 3636 800' m 0 Transmittance. 3%: (mécrons) a symetrical structure with ...
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