Exam I Spring 2014 ‘Name. Ke y Room Student ID, Seat Number, ‘The exam consists of 10 questions on a total of 10 pages, including periodic table. 1 no 2 ___no 3. no 4,0 5. no Co er/i0 7 no 8% no oid 10.10 Regrading: All requests for regrades must be submitted in writing within 48 hours of the return of the exam. You must explicitly state what has been misgraded and why it is an error. The entire exam will be regraded, which could result in points being added or deducted overall.1. (10 points) a) (4 points) For the compound illustrated below indicate the most acidic hydrogen and indicate its pKa, n 9, = eS fg Cyt phone? ieee inert +2 +2 b) (2 points) Identify all of the functional groups found in the molecule illustrated below. -\ Foy (‘ee Bese ee ae tate? ether +l ©) (4 points) For the compound illustrated above, draw a constitutional isomer that is more acidic. Please indicate the identity of all functional groups. coro lic bow F ees ae 2 also acegtehle Csever| possibility esq & mony) allzere +) ' aloabo| +1 oN OH ne jhe kotor #1 pars2. (10 points) For the molecule illustrated below, please answer the following questions: locoliae& er lochized, aN ~ SS sp> a oo 7 a) (4 points) How many carbon atoms are present? How many hydrogen atoms are present? 12 re Carbons: |] Hydrogens: | ') (3 points) Indicate on the above structure the hybridization of each heteroatom. + [Fo p eoch ©) ( points) Indicate on the above structure whether each lone pair is delocalized or localized. + | Far each 3. (10 points) G points) Indicate the hybridization of each atom. spon spe +1 fer each (7 points) Draw an orbital overlap picture for the molecule illustrated directly above. -| far egch error4. (10 points) Draw all significant resonance structures for the compounds illustrated below. Circle the most significant contributor in each case. a) (5 points) _—— @ alm <— +2 For \D oO hy ROT eoch tl For mat J signi Ficont -| for insignsFreat -2 For nrost signiftcont unoceptehle, b) (5 points) a - v eh. uN Zp <—_ UN — SK ° ° 2 iby mast cigniffert5. (6 points) Indicate the most acidic proton on each compound illustrated below. O° 9 ‘NH s oO ‘O 42 Fon ech corrat answer Neeg to hore Cire lech the peiton ; b) (4 points) In which direction does the equilibrium lie? What is Ke for the following process? =z x 5 HCl + Ho Glen fog pka=-8 (2 i9 he pka=-2 +2 For chirction +2 «OCF or arvez ie Keg ela Volve-6. (10 points) a) (4 points) For the acid/base reaction illustrated below, predict the products. Show the mechanism with clearly drawn arrows (only consider left to right). on RY © | i ry +2. for correct pradvots 42. Pon corveat ovvows ont +2 (fF ovylprtene is chepritoncte! with correct orrows ») (4 points) In what direction does the equilibrium lie? Briefly support your answer using base stability principles. Lert +l ARTO jeqetive chovge Vs More TO Soh on mace electvonepoting atom. CNitregen ts more a clectronegctine than Corn ) Foo explenction ©) (2 points) If the above reaction is carried out in HO as solvent, what would you expect the products to be? m+ yh. me 42 fon cornet. ansivep7. (10 points) a) (5 points) For the structure illustrated below, use resonance structures to identify all carbons that are electron deficient. Mark the appropriate carbons in the figure below with a 8°, + 9 et fee exo ie ee 4 wrvet St er s -| For incorvecd- S~ £2 for a correct resonence Stref Ure b) (5 points) For the structure illustrated below, use resonance structures to identify all carbons that are electron rich. Mark the appropriate carbons in the figure below with a 5. SxOs io +2 Fon ech Oo + a s S -l For @ — B J incorrect & oJ ‘ 2 tOL for a covet = structure8. (10 points) a) (5 points) Draw the conjugate base of the following two molecules illustrated below. Nw NH NH, +2 Fon ore f * ° i So? covet Z Z rc) Ss +S Fon hath o, covet cay i i ») (S points) Which of the two molecules is more acidic? Briefly support your answer with appropriate figures and/or text. he nejotive chowe con ay — GSGie debeclrae to hath nitregens - 2 5 +2 for covet molele +/-2 Fe 9. (10 points) 2 for nee explonotion 8) (6 points) Hydroxide is not suitable base for deprotonating an alkyne, why? Use pKa values to support your answer. = Con = — =o H,0 pka = 2s pKka2I5.7 ae MA’ Reoction Favars wecken acd? carved chirectin Cleft side) hosel on pKa 4 Fap ech plea, +2 Fon answen +b) (4 points) Propose a base that would be suitable to deprotonate the alkyne. I acegp the uy, a et a amine \7? epratorctel =o \ ? +4 fan comet answer10. (10 points) a) (S points) Please rank the following compounds in order of their acidity, with 1 being the most acidic and 4 being the least acidic. NHo SH OH NH a0 0 : 2 2 +2 Fan Strongest +2 For weoleyst +] Fao mre two b) (5 points) The barrier to rotation of the indicated bond of an amide is significantly higher than a typical C-N bond, why? resonaxe hy brik tial _dbovble ma eee we pa alleatobion +S For correct : answerPERIODIC TABLE OF THE ELEMENTS F—Jatemic Number | symoor +.008}Atomic Weight 140.1| 409] 144.27 145) per pee lm [pau inp 222.0f 230] 238 Scratch work: 10