Exam 1 Key - Name Exam 1 Tuesday Answer as many questions...

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Unformatted text preview: Name Exam 1 Tuesday, October 25, 2011 Answer as many questions as you can in the time allowed. Please be as clear and concise as possible. 1. Benzazepril (lotensin) is a generic drug for the treatment of high blood pressure and heart failure. ‘ a. Identify all the functional groups in benzazepril. Classify as primary, secondary, tertiary where relevant. b. Identify 2 sp3 hybridized atoms and put a square around them. Identify 2 sp2 hybridized atoms and put a triangle around them. a 2. a. Draw the Lewis structure of malononitrile (NCCHZCN). b. Malononitrile is somewhat acidic (pKa = 11). Draw its conjugate base. Draw the most important resonance structures for the-conjugate base. . l c. Using the following pKas, draw the structure of a base which can be used to deprotonate malononitrile. H28 (pKa = 10); HCN (pKa = 9); CH3OH (pKa = 16); CF3C02H (pKa = 0) ago” d. What is the equilibrium constant for the reaction of malononitrile with your base? Kola/05 Name 3a. For each of the following compounds, draw the full MO energy diagram. Make sure the relative energies of the orbitals for all three compounds are clearly indicated (you’ll need this for part c). Clearly label the HOMO and LUMO on each diagram. H\B/H HYH H\_‘/H H H H 4 ,___ 0/?“ ’- Fl 32' ,__ _... ~ A,” A ’— -- LUW‘O L “'— L HOMO 0/ / art: ’i—LHOMO ' 7% 4.“ 419 46%HMOQ, % % it b. Draw the HOMO and LUMO for each of the above compounds. HOMO: 63:0“ “CL/:19 H H. ;c\ c. Of all three compounds above, which has the highest HOMO? Which has the lowest 'LUMO? ~ (V); A” J41 HOMO (kw lq/ lav“) LVMO Name 4. Rank the following in order of decreasing boiling point: 0 H o \ o AOH \H/ / \ /\ ' /\OH O . I, 3 H 5‘“le) 2. '5. Rank the following in order of increasing boiling point. N «gs g [’(owtfll . 6. 2,2,4-Trimethylpentane is a compound that is used as the standard for gasoline octane ratings. Draw Newman projections of all possible conformations around the C3-C4 bond. (There are 4.) Rank them in order of stability. Mg m CV8 0:; C“) H. n /H A ' % H CH) M CH5 I4 ’14 ,5? A:% a _ ' . L Jug L /» Within 3 I “m . Name 7a. Identify all the isomers of 1,4’-difluoro—1-methylcyclohexane. Draw both possible chair conformations of each of these isomers. Circle the most stable conforr'nations of each isomer. ' (IZH) - _ F— 9H C1) R {j CH} V C”; b. Which isomer is more stable? Which is more polar? (’3 I”; Mme r (\ii IS Mafia. Poi” , 8. Rank the following compounds in order of basicity (from most to least). AN/ . /N\ A0 2 q I, moi): ; [cach 9. Rank the following in order of increasing heat of combustion (more negative AHcomb): O A It 3 l-émciifij} q 7 z Name 10. Melamine and cyanuric acid are highly symmetric molecules. For each observation below, briefly explain why (and remember a picture is worth 1000 words). H H2N N NH2 , o N 0 NH N / N HN melamine\i/ I cyanuric acEH/ NH2 0 a. Melamine and cyanuric acid are both soluble in water. _ / H / M 80%, M M 6 M J‘ NAHrv-O‘H "'O‘H Cyawl‘g “(7) AQVLQ May? 0 V \\N‘ H/ \H :0 A Wat” a, b. One of these two compounds is much more soluble at low pH, the other is much more soluble at high pH. Label each graph with the correct compound and explain. solubility solubility ‘ " pH ck 1 PH . Mme ~ “*8; 5 «WM was—“6 [it HL MaM O 0 6 ' ai" law H: » 51040 3/ Y M“ J g Wlamlm 9“ ’49, 1" “‘a “to (“firm c “Effigy/g é‘g M}, C/m‘wvaficvdz NH» . o a «CHM A; 0. Though both melamine and cyanuric acid are soluble in water, a 1:1 mixture of the, two compounds is totally insoluble. 0 3 f0 H? 46.49 M Vvafhy I \M/M ?/ Quiz 4’ m8 dbl/G OVL’EKV‘équ A "44/ \ \F‘ Mia/“MR WW} (ya/‘wfcgcm’f an/ H‘ JCMLK /\’\"O uscv <// HrbonJ. die; A, _ P _ ’7’ CL Ace) That“ no Q—C a, C'H'Earwaj‘ Query cam/a 5.4,le by wmAkS‘i‘tW‘ d. Melamine/cyanuric acid is also used as a flame retardant. /’ fl /1\ C ( g 9 Me 7 " V ,-:—.-,«=:>- , _ ,. Name ...
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This note was uploaded on 01/18/2012 for the course CHEM 335A taught by Professor Michael during the Fall '11 term at University of Washington.

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Exam 1 Key - Name Exam 1 Tuesday Answer as many questions...

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