CHEM 231 (Davis) Organic Chemistry FINAL EXAM May 15, YOUR NAME (Last, First, M.I.) DISCUSSION SECTION #53 (5 Points)

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1 CHEM 231 (Davis) rganic Chemistry FINAL EXAM May 15, 2006 YUR NAME (Last, First, M.I.) DISCUSSIN SECTIN #53 (5 Points) Initial of last name Instructions Please fill in your name in the space above and on the next page Please put your discussion section number in the space provided. Print the initial of your last name in the box above Please sign your name under the Honor Code acknowledgment 1

2 Name CHEM 231 Final Exam May 15, 2006 This exam is worth 300 points Notes The exam period is 120 minutes. University Honor Code Acknowledgment I have not given or received assistance on this examination. Signature Points Discussion Section (5) Part 1 (150) Part 2 (70) Part 3 (75) Total (300) EXAM BEGINS N NEXT PAGE 2

3 Part A Answer the following questions 1. Draw a structure for (R)-2-chloro, (S)-3-hydroxy-butane 2. Indicate the hybridization at every non-hydrogen atom in the following molecule: C C C H 3. Add electron pairs as needed to make octets, then calculate the formal charge on all the non-hydrogen atoms of the following molecule: N C H 4. What are the approximate bond angles in the following molecule? a c H C C C b C H H d a= b= c= d= 3

4 5. Draw Newman projections for eclipsed and staggered ethane (C 2 H 6 ), looking down the C1-C2 bond of the molecule. Eclipsed Staggered 6. Draw Newman projections for the anti and gauche conformers of butane (C 4 H 10 ), looking down the C2-C3 bond. Anti Conformer Gauche Confromer 7. Draw 2D structures for an isomer of 1,2-dimethylcyclohexane that is chiral and draw the structure of an isomer of 1,2-dimethylcyclohexane that is achiral Chiral Isomer Achiral Isomer 8. Select the isomer from question 7 that has 2 chair conformers of different energy. Draw the 2 chair conformers and clearly depict the axial and equatorial substituents at the C1 and C2 positions of 1,2-dimethylcyclohexane 4

5 9. Rank the following cations in order of increasing stability (4=most stable, 1= least stable) + CH 2 + C( ) 2 + CH( ) + C( ) Draw a structure for the bromonium ion that is formed by reaction of cis-2-butene (cis CH=CH ) with molecular bromine (Br 2 ). 11. Write an equation for the acid/base reaction of HCN with methanol ( H). Label the stronger acid (SA), the stronger base (SB), the weaker acid (WA) and weaker base (WB). 12. Using the above equation and the following pk a values, circle true or false for each statement below: + H 2 pka= -1 HCN pka= 9 H pka=18 a) HCN is highly ionized in methanol TRUE FALSE b) HCN is a Bronsted acid TRUE FALSE c) HCN is 9-fold stronger acid than methanol TRUE FALSE 5

6 13. In the reaction A + B C+D write an expression (equation) for the equilibrium constant (K eq ) and write an expression (equation) that relates the free energy change of the reaction ( G o ) to the equilibrium constant. 14. Draw resonance structures to illustrate why all C-C bond lengths are identical in benzene Å 1.34 Å 1.40 Å 1.40 Å 15. Use structures to illustrate why γ-pyrone is more basic (i. e. protonated more readily) than cyclohexanone. Make sure to compare the 2 systems clearly and completely. γ-pyrone 6

7 Part 2. Mechanisms. Show a step-by step mechanism for the following reaction. Make sure that you account for the proper stereochemistry (20 pts): Hg(Ac) 2 H/THF CH3 Hg(Ac) b) Based on the mechanism from a) above, predict the product of the reaction below (10 pts). H Hg(Ac) 2 THF (only) Note: No methanol added, only THF as solvent 7

8 2. a) For the reaction below, provide an arrow pushing mechanism that explains the transformation. (15 pts) HBr Br 1 2 b) In theory, product 2 above could be a mixture of stereoisomers. Draw the lowest energy chair conformation for the thermodynamic product of the above reaction. Make sure to clearly indicate axial and equatorial substituents for those carbons that have non-hydrogen substituents. (5 pts) Br 2 8

9 3. a) For the reaction below, provide an arrow pushing mechanism that explains the transformation of the enol to keto form of acetone (15 pts) H H 2 CH 2 Enol Keto b) Based on the bond dissociation energies below indicate the H o for this enol to keto transformation: C-H sigma bond 95 kcal/mol C-C sigma bond 100 kcal/mol C-C pi bond 60 kcal/mol -H sigma bond 100 kcal/mol C- sigma bond 100 kcal/mol C- pi bond 80 kcal/mol H H 2 CH 2 Enol Keto H o = 9

10 Part C. Problems 1. (50 pts) Bromination of Alkanes a) Write the radical chain reaction for light-initiated monobromination of methane. Provide equations for the initiation step, each propagation step, and the overall reaction. Also, calculate the H o for each propagation step and the H o for the overall reaction. Values for bond dissociation energies are as follows (35 pts.): Initiation Step Bond Dissociation Energies C-H σ bond 95 kcal/mol Br-Br σ bond 45 kcal/mol H-Br σ bond 90 kcal/mol C-Br σ bond 70 kcal/mol First Propagation Step H o = Second Propagation Step H o = verall Reaction H o = 10

11 b) Provide an energy vs. reaction coordinate diagram for the above reaction, starting with the first propagation step. Make sure to designate the energies that you have calculated on that energy coordinate diagram. Clearly label all intermediates and transition states on the diagram. (15 pts) Energy Reactants from 1st Propagation Step Reaction Pathway 11

12 2. (25 pts) Protonation of the following diene can occur on any 1 of 4 carbons. Draw all 4 carbocations that can result from protonation: a) H + 4 possible cations b) f the 4 possible cations, draw the structure of the most stable carbocation c) Draw 2 resonance forms for your most stable carbocation 12

13 d) Based on your above analysis in part c) draw structures for the 2 possible products of the following reaction. HBr?? 13

14 BLANK_NTHING GRADED 14

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