Exam 1 Key-Fall 2007

Exam 1 Key-Fall 2007 - 1. (25 pts) The structure pictured...

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Unformatted text preview: 1. (25 pts) The structure pictured below is Penicillin G, an antibiotic that shows high in vitro activity against a wide variety of bacteria by inhibiting the biosynthesis of cell walls. (3) a. Penicillin G is typically administered as a potassium salt resulting from the formation of a carboxylate anion under slightly basic conditions. Draw the structure corresponding to this anion (conjugate base), and draw the resulting resonance structure: Carboxylate Anion Resonance Structure b. Circle and clearly label three different functional groups. Mull , emboxuub natal , s‘u Lfiolfi» c. Determine the hybridization of the atoms indicated by the arrows above. Write your answers in the appropriate spaces below. (1) {f‘ 9r ep’ (2) 5F (3) 4P7 2. (16 pts) Give the products of the following acid—base reactions and indicate the direction of the equilibrium by circling the dominant species (the side to which the equilibrium lies). e x + NH2 = 3. (16 pts) Circle the most acidic hydrogen in each molecule, andjustify your choice by using appropriate pKa values (Compare for the pKa for each functional group). ®o ‘——: H4 PM; t6 Plait”: 4. (8 pts) a. List the following carboxylic acids in order of decreasing acidity, where 1 is the strongest acid and 4 is the weakest acid. 0” Cl OH OH CI El b. In one word, give the name of the effect responsible for this difference in acidity :‘Moffivf'lm 0H Cl 5. (6 pts) Give the IUPAC name for each of the following compounds: a. Br I CH3CHCH2CH2CHCHZCHZCH3 l oH CH3CHZCCHZCH3 I CHZCHZCH3 3- “its (7 3 ‘ luxmwl/ 6. (12 pts) Draw skeletal structures of the following compounds. a. 5-ethyl-2-methyloctane b. propylcyclopentane c. 1,3-dimethylcyclohexane d. 2-methyl-4-(l-methylethyl)octane 7. (9 pts) For each of following pairs of compound, circle the one with the higher boiling point: a. 1-bromopentane VS b n-butyl chloride VS isobutyl chloride c VS diisopropylamine 8. (24 pts) Consider l-bromopropane, CH3CH2CHzBr a) Draw all possible Newman Projections for the conformations about the C1-C2 bond on the following template starting with the configuration provided, and rotating clockwise by 60° : 120 180 240 300 360 Torsional angle (3 60 b. Draw the most stable conformer below, and label all eclipsed, gauche, and anti interactions using arrows labeled E, G, or A respectively. 81 [A] n H H H CH), C. Draw the least stable conformer below and label all eclipsed, guache, and anti -interactions using arrows labeled E, G, or A respectively. a lE7 CK}. BY n H H \ / A *\ E E Ema 9. (38 pts) The following molecular anion (structure 1) or formate is formed by the deprotonation of formic acid. a. Draw the Lewis dot structure for the formate anion 1 and show all appropriate resonance structures and formal charges: :O: 09 ‘ ' H . 929:0” @0)\H fir! b. Sketch the bonding sigma molecular orbital for the formate anion 1: .‘0_ 4 u c. For 1, how many electrons are present in the following: i. 0 bonds: 6 ii. lone pairs: 8 iii. It molecular orbitals: (71/ (1. Draw the three at molecular orbitals of formate anion 1 in the order of increasing energy with the lowest energy orbitals at the bottom. Fill in the appropriate orbitals with the available Jt-electrons using lines or arrows, and label as B, NB, or AB. Bonding (B), Non- bonding(NB), or Anti-bonding (AB) W-electrons AB e. What is the bond order between for each of the carbon oxygen bonds ? Are they the same or different ‘? Why ? banal «WU/r, [,f re§0rwmw mw/U/s Hm 7' imoi eWij V" betk Clo W 10. (30 pts) Write a mechanism for the light-initiated reaction of cyciohexane with chlorine to give chlorocyclohexane. hv 0L Initiation: ‘ \ , M “ Soi' + Propagation: Termination: a?“ “ 2" ~——-———) In E) NH O. + 'O A» (3—D ...
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This note was uploaded on 03/23/2010 for the course CH 54410 taught by Professor Sessler during the Spring '10 term at University of Texas.

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Exam 1 Key-Fall 2007 - 1. (25 pts) The structure pictured...

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