CHM3217 F08Exam1Solutions

CHM3217 F08Exam1Solutions - CHM 3217 Organic / Biochemistry...

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Unformatted text preview: CHM 3217 Organic / Biochemistry I Exam 1 Fall 2008 Print‘Name SQ as;le % In the white spaces below each question or problem, neatly provide a clear, concise solution. Organic Structures, Molecular Orbitals, and Bonding l. (A) Draw structures for seven constitutional (structural) isomers of C4H30 (7 points). a £731 l Am Mm few few fiw @ $3“ @fi. gé 3H f ~ . I. I We» W, a 6 ma l W / o\ W“ JR , H r ~ Warsaw” MW 7. I, m“ ‘MW’W afififirmléflwfifi fli‘rlo) mass; “5% , a an. ole. aisles,” _ Kmmwg were” emerging )K/flu (B) Draw one representative Lewis structure (using dashes for bonds between atoms, dots for lone pairs, and formal charges where appropriate) below each molecular formula (6 points / 2 points each). C4H5N W CH3CON(CH3)2 - C5H5N02 sfi W a» s m iv .\ Maw s a ... $2» gills as a a here as . ’ a; g Q ~. figfifiip a g R}, H. gigs 9 w “:33 ‘ H “ :mm m a 2% AM“ as. @313 7’ We? U r flak) ‘ ‘ mm a ’1 IAWWQZY’E/Wf‘ {:36 mfflmfls’ww f? q B “a . . _ -“". ‘t a (C) Circle and name the ten functional groups in the followmg molecule (10 pomts): R lermlfis “Azéa'lfihflgg 2. Consider the at molecular orbitals of the pentadienyl radical: Place the correct letter (ans) of the MO in the blanks below. (4 points / 1 point each) (A) Which MOisthc HOMO? b (B) Which MO is the LUMO? a» (C) Which MOisvt*5? C (33) Which MO would be the HOMO if this radical is ionized to the pcntadienyl cation? fit Acid Base Behavior and Resonance 4. Use inductive and resonance stabilities and structures of the conjugate bases to explain the following trend. Use the space to the right of each molecule to make your points. (8 points, 1 point each) CClgCOzH CH3COgH No2 OH Phenol CH3SH CH3OH CH3COCH3 HCfiCH at we ‘ a ctr-5 washes pKa Q m '1 stag? asfi’ Sight Mars: 5 1 fl sf"- ifi W 0.5 maéwfiegeewfiegmfiwa ! 2% W mm fiflflé mg" {matte Mists-'33"- sss “:3; r as 4» saw seer-it'th 7.2 , m Mae “ iarga areas: "a égfitmflé‘? Chi 3 g ' t arias. errigartwa eatiW fi’g‘ggw 10.3 +2949? «$5.1... i ’. f? Emmi tile“: 4-1 5% s -~ fie slashes! gamete/tie is? W a fihdaféfeé’fifi ea ,rsfstttséssfiagfi s 5. Draw three additional significant resonance structures for the following cation: (5 points) 0 ® Alkane and Cyleoalkane Stereochemistry and Conformations 6. Sighting along C1 w C2 bond of l-bromopropane, draw three Newman projections showing one conformation of greatest stability, one conformation of intermediate stability, and one conformation of least stability. Draw and label (eclipsed, etc.) them below in order (left to right) from greatest to least stable. (6 points) vi gett- :;. E??? 1? a m, ._ __ m E M I: I: «a. M r "'5 ‘. \ .:- g lei fleetaaaagw Egg“ Effigy fig 7. One CH3 on CH3 gauche interaction and one CH3 on H diaxial interaction each account for 3.8 kJ/rnol of strain. Draw the two chair conformations of trans-1,2«dimethyloyclohexane, calculate total strain in each in each structure, and circle the structure with the most stable conformation. (5 points) . “gag, %% é! w I. a» { ’ a ‘ A,” a 6% %a tease ., m , a. {6:33;}? a“ Lag” 3 “$5 m ‘ W a team? all». Mechanisms and Reactions 8. Using curved arrows to Show electron flow, Show a mechanism for all three steps. Be sure to Show structures of the intermediate bromonium ion and cyclic carbocation. (10 points) "B119" Mum-man» Bromomum ion ~—->~ Cychc carbocatlon Bromo— peroxidase Base Br 9. Show a mechanism and predict the product for the reactions below: Don’t worry about stereochemistry here. (5 points) 10. Predict the major product(s) of the following. Show stereochemistry if applicable. Do not provide mechanisms here. (12 points / 2 points each) (A) HBr mew-“mah- 80°C (3) 1)0s04 2) NaHSO3, H20 (C) OH =9 ® SWWL L”? f H 31-120 E as W 3% WWW “"9 (D) ; ,M . ; 913213, THF *3” 5% 2)}1202, 0H9 ‘ r g .1 “33% (B) a 1) Hg(0Ac)2, HZO/THF 2) NaBH4 fl” . (F) . ‘ \ MIA—lg» Mew-’Tfiaefié fiwégfi‘g ‘ 3% gfi May 6"“ 11. Supply the missing reagents over/under the arrows. (6 points) He. Lt‘amé. tee 6 \ ‘ OH i; m? e l Alkene Nomenclature .4». efifi" 12. (A) Draw the structure of (Z)~2—hydroxymethyibut—Z—enoic acid. (3 points) (B) Give the IUPAC name, including stereochemistry, for the following structure. (3 points) / \3 \ a - W “t” feéefie‘ft Bonus Show the mechanism leading to the product. You must consider stereochemistry here. (6 points) ...
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This note was uploaded on 01/11/2010 for the course CHM 3217 taught by Professor Keaffaber during the Fall '09 term at University of Florida.

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CHM3217 F08Exam1Solutions - CHM 3217 Organic / Biochemistry...

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