FinalExam_Key - Circle the section in which you are...

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Please write the first three letters of your last name in the above boxes Organic Chemistry CH 310M/318M Dr. Jonathan L. Sessler Final Exam Friday, December 12, 2008 Name:_______________________________ UT EID:_____________________________ Signature:____________________________ NOTE: There are no regrades on the final exam. Good luck, and have a great winter break!
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2 pts: 1. Resonance structures (32 points) a. Draw the two most plausible resonance structures for nitromethane (CH 3 NO 2 ) in the boxes below. Use curved arrows to show the flow of electrons. b. Draw the two most significant additional resonance structures for the enolate ion in the boxes below. Use curved arrows to show the flow of electrons. c. Draw the two most significant additional resonance structures for the following structure. Use curved arrows to show the flow of electrons. d. Draw the two most significant additional resonance structures for the following molecule. C H H H N O C H H H N O O O O enolate O O O O H O N O H O N O H O N O N N N N N C N / 32
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3 pts: 2. Complete the energy diagram for 1, and label all eclipsed (E) and gauche (G) interactions responsible for their relative positions on the energy diagram. While you should pay attention to the relative levels between the different maxima and minima, you do not need to estimate activation energies. Hint: Start with the structure in the lower left and rotate the front carbon 60 o clockwise each time. (20 points) H H 3 C CH 3 H CH 3 H 1 / 20 E Torsional Angle ( º ) 0 60 120 180 240 300 360 H H CH 3 CH 3 CH 3 H H H CH 3 H CH 3 H 3 C H H CH 3 CH 3 H H 3 C H H CH 3 H 3 C H H 3 C H H CH 3 H 3 C CH 3 H H H CH 3 H CH 3 H 3 C G G G G E E
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4 pts: 3. Give the stereochemical relationship between each pair of structures by writing one of the following in the box provided: Same compound ( SC ), constitutional isomers ( CI ), enantiomers ( E ), or diastereomers ( D ). Assume you are working at room temperature and that you have free rotation around unrestricted single bonds. (16 points) a) b) c) d) H H CH 3 Br OH H 3 C H H CH 3 HO Br H 3 C and H H CH 3 Br OH H 3 C H H CH 3 H 3 C Br HO and H HO CH 3 Br OH H 3 C H H 3 C OH Br OH H 3 C and H HO CH 3 Br OH H 3 C H Br OH H 3 C OH H 3 C and / 16 E SC D CI
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5 pts: 4. The following is the structure of cortisone. Fill in the chart appropriately for the labeled atoms. (18 points) Hybridization Avg. Bond Angles Chiral Center? If Chiral, (sp 3 , sp 2 , sp) about the atom Yes or No R or S a sp 2 120 o No b sp 2 120 o No c sp 3 109.5 o Yes S d sp 3 109.5 o Yes R e sp 3 109.5 o No f sp 3 109.5 o Yes R / 18 O H H H OH O OH O a b c d e f cortisone
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6 pts: 5. (8 points) A. Draw the conjugate acid of each of the following: 1. NH 3 2. Cl - 3. OH - 4. H 2 O B. Draw the conjugate base of each of the following: 1. NH 3 2. HBr 3. HNO 3 4. H 2 O 6.
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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 at Austin.

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FinalExam_Key - Circle the section in which you are...

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