Test_I_3331_J - T ta 5W1 “F ’77“MEM 333...

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Unformatted text preview: T? ta 5W1 “F ’77“MEM 333;; Nomenclature (9 points) A. pu Give the lUPAC.name for each of the following compounds: ’8 :1: O I '31, ( I! Q Q 6:: Q a :1: I0 0 .L r a RT, f I I I Draw! the structure that correspc-rtxwith the foliowé :::- com S'L‘fld ’ h LI ' a: A- I h h 4—sey uLyn-3,a-umcthylcctcns -- _ [ .l 2. Hybridization/molecular orbitals 2A. Indicate the hybridization state for”each indicated carbon and oxygen atom in the following molecule. Place your answers in the boxes provided (5 points). 2'8; For the following organic species, indicate the hybridization for the oxygen atoms. Please draw a three dimensional orbital picture'for the entire soeciee and place your ans-Hers in the boxes provided (6 points]. ’? 3. Resonance (11 points) Draw gfl the resonance oontributors for the foliowing species (10 points). 9‘ r a I @ CH3 ‘ " \KZZ firm—"9 HCJ), ii . rLGQL I<%Vm:*mf’i Y—Gfi .t/ Cir-ole the major resonance contributor {circle omit.r one structure) {1 point}: F) Wok 1" a Q T] 4. LEWIS STRUCTURES: Total = 9 points, 3 points each Provide a proper Lewis structure for each of the following compounds. (Place your answers in the boxes provided.) A.CH~COCH3 d QlA—uw' ow Lannie/fl Llellfia o3 F KanSVoérfl ‘fltll-«Hlkglwvx .Q\QC.'T{L.A"¢=_-— n1] BSEHCIS J \ ( NJ-r-ILGf-rr M g 0 Q \m (S—‘Ixfl UI rw J: Qxckkuwasu CIA—Um. : ' ex.) _ .S'IH‘CHQNzo '2'" I; I *§( ) Km es‘w‘j rvw {IQEilT‘IUwD {32/ alarm-Ir M\ ) L—_~l_—_.____ \mraimj cog-(WW (“V W"! 5. Electron pushing (8 points). For the foilowing reactions use curved arrows to indicate the movement of electron pairs associated with bond breaking or formation. 1M1 A. I ' - . 8H3 + H3,cr"‘”5““~cH3 " H3BS(CH3)2 1 :8” oh 8. H3C\ CH3 r 1"“13‘3’ H30 H )ng J, gar Ho H3O CH3 H30 I \ r” \ Br '5 {213 r c. NH3 + CH3CH2CI CH3CH2NH3CI LS“ m1 6. lsomers (10 points). identify the foliowihg pairs of molecufes as "identical", “different” (Le. not isomers). u u “structural isomers _ stereoisomers". Place your answers In the u . A. (2 points each) (a) H3C—CEN H30— 25: i ' .. i {b} I ' | xxx/P” //\\//’J or .H H ,H *1 )z Ho m )fi (c; ,.v—1\ , CH3 mo H H C! of the compound I. The five member ring as shown in M E 1 w“ w d1 ' ' ' _- —1 pr Como-ooh ! _ I! Ev CH? I i J“ x T O k I. : . . l < K E Qfljxfl’r‘? f CH1 I , 7. Dipble Moments : Total :10 points A. in the box provided state whether each molecule is polar or nonpolar. (3 pts. each) B. For the molecule below, draw an arrow representing the net dipole moment. Place the arrow in the box provided. (4 pts.) 8. Physical Properties : Total = 9 points, 3 points each A. Place the following compounds in order of increasing boiling point. (blow-est, . ‘ Szhighest} Place numbers in boxes provided - ‘1 \‘ .' \u‘lw—fi/ \flb—J}; \w—jf r“ 7 ' l“? l '1 L4 l.___l Wt Lei M W: r7 '2?" l 8. Place the foilowing compounds in order of increasing solubility in hexane. (1: least soluble, Szmost soluble) Piace numbers in the boxes. CH30H20H2F ' LiF - CH30H20H20H3 [I D \-fl3r 5W Lexi Wfligflfi C. Piece the following compounds in order of increasing solubiiiry in H2O. (i=ieast soiubie, Szrnost soiubie} Piace numbers in the boxes. ' ongongcngcegoe onioezmzngcwi3 CHSICH2)4Q(CH2)4CH3 9. ACID/BASE : Total = 9 points A. Place the following compounds in increasing order of acidity. (1:!988t acidic, 3=most acidic) Place numbers in boxes. (1 pt. each) 8 ' {ffir [1 CH OH OH CH can CH CH SH 3 2 3 3 2' LyKJ Y E E El "Wrd3fl B. Given the pKa values below, predict whether the equilibrium lies to the left or the right for each equation below. lndicate your choice by writing the word "Lei-t" or “Right” in the box provided. (3 pts._ea_ch) - .3 : ' _ ‘ «(fl—um + .. t. cnalsz + CHacOZH ——r CH3NH3 + CH3002 rfla it“)? i l 73 ._.___J -- l +— 2 '" why H2O "' F ,. fit 2“ o j [631"] \ 2 7) " Selected pix”; valu es: pKa H30; - 1.74 CHqC 0,44 4.75 NHd': - 3.1;. CSHSOH 9.9 CH3NH3+ 10.6 H20 15.7 CH3CH2C'H I 15 CHsNHz 37 5 NH3 :38 CL'ESCHg, 50 10. Formal charges (9 points) Calculate the formal charges on each carbon and nitrogenatom In each of the following compounds or chemical species. Place your answer in the box provided‘ H ‘H C 5 '7) I if H v.1 a. H~—C—4'N—~OI ‘ i .. . N : H 1-i 2 .. rw—‘— o HmCHH = l0 11. Molecular orbitals and energy diagrams a. Construct the bonding and antibono‘lng molecular orbitals using the LCAO (linear combination of atomic orbitals) approach for the following possible molecule and draw the corresponding energy diagram (4 points). H82 _. _ l:- K// lli. 7‘. l p ‘7 'o. Do you think this moiecule would be stable or unstable? Circle your answer below - {l pomt}. stable ' unstable 11 ...
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