1. Final Exam Instructions:
1. You must bring a #2 pencil. YOU MAY NOT USE A CALCULATOR. You MAY NOT use the formula sheet.
2. Cell phones are not allowed. If you are observed with a cell phone in use or in sight, you will receive a grade of ZERO on the final exam.
3. You may not leave the testing room for any reason. If you must leave the room during the exam, you must turn in your exam first, and you will NOT be allowed to continue after it is turned in.
4. You will have exactly 120 minutes to complete 70 multiple choice questions. If you are late, you will have less than 120 minutes to complete the exam.
5. Your grade will be determined as a percentile of the national average or as a raw percentage, which ever score is higher.
6. You will be provided with a test booklet which has abbreviations, a section of the periodic table, and some molecular structures, answer sheet, and scratch paper.

2. Point Distribution
The exam grades will be “curved” based on the national norms as follows. Out of 70 total questions graded for one exam booklet
score
points
Points
67-70
150 51
122 37 79 23 49
65-66
149 50
119 36 77 22 47
63-64
147
116 35 75 21 45 62
146 48
111 34 73 20 43 61
144
108 33 71 19 41 60
143 46
104 32 69 18 39 59
141 99 31 66 17 58
140 44 96 30 64 16 57
138 92 29 15 56
135 42 90 28 14 55
134 88 27 13 54
131 40 86 26 12 53
128 84 25 11 24 52
125 38 81 10

3. Point Distribution
The exam grades will be “curved” based on the national norms as follows. Out of 64 total questions graded for the other exam booklet
score
points
Points
61-64
150 46
119 32 75 18 43
59-60
149 45
116 31 73 17 40
58-59
147 44
111 30 70 16 38 57
146
108 29 67 15 35 56
144 42
104 28 65 14 33 55
143 41 99 27 63 13 54
141 96 26 61 12 53
140 39 92 25 58 11 52
138 89 24 10 23 51
135 37 87 9 21 50
134 36 85 22 8 19 49
131 82 7 48
128 34 80 20 47 6
125 77 5

4. Final Exam Topics:
Naming: IUPAC and common names we covered, E/Z notation
Reactivity: all reaction conditions we discussed are fair game, strengths of organic acids and bases (based on stability of their conjugates), strengths of nulcleophiles and electrophiles, electron withdrawing or donating groups and their effects on the ring, drawing transition states, reaction coordinate diagrams for reaction mechanisms, polymerizations, kinetics and rate law, thermodynamics
Drawing molecules, formal charge, resonance, recognizing aromaticity, sp, sp2 sp3 hybridization and molecular geometry,
Stability: Newman projections, gauche interactions, cyclohexanes (axial and equitorial position), 3˚, 2˚, 1˚, and resonance stabilized carbocations, HOMO and LUMO, degree of substitution on a C=C,
Isomers: constitutional, chirality, stereo (diastereomers, enantiomers), stereocenters, R and S configuration, meso compounds, racemic mixtures
Spectroscopy: IR, MS, NMR (proton and carbon), optical activity, UV

5. Organic Chemistry Olympiad 2010 Rules
The class will be split into 2 teams.
Each team will send a team member to the front of the room to compete heads up (no team member may participate in heads up twice until all team members have participated at least once). No coaching will be allowed during heads-up competition.
Heads-up competition will result in one of the following outcomes.
Both competitors choose not to answer the question
In this event, the competitors will consult with their team. During team consultation, a free-for-all will ensue, and any team member may submit an answer on the board. The first team to officially submit a correct answer will receive 1 point.
Both competitors answer the question correctly
In this event, the competitor who submitted their answer first will receive 2 points for their team, and the competitor will get one point for their team.
One competitor answers correctly and the other does not
The competitor who answers correctly will earn 2 points for their team.
Both competitors answer the question incorrectly
No points will be awarded.
Competitors may NOT look at each others work until they have both officially submitted their answers.

6. Of the following molecules, which is (Z)-3-pentenal:
A B C D

7. What should the product of the following reaction sequence be?

8. Draw the following molecule with the correct formal charge:

9. Name the following molecule:

10. Give reagents that could be used to make the following compound via Diels Alder.

11. Give the most likely product that would form the following reaction sequence.

12. Give the most likely product that would form the following reaction.

13. Which of the following molecules should have a peak in the IR spectrum above 3000 cm-1 and a peak at around 1700 cm-1
A B C D

14. True or False: If benzoic acid were substituted with an electron withdrawing group in the para position, the resulting compound will have a lower pKa than benzoic acid.

15. Give the structure of a ketone that would give 2 13C NMR peaks but has 3 total carbons.

16. Give the most likely product that would form each of the following reactions.

17. Give the hybridization of the indicated atoms in the molecule below.

18. Label the following molecules if they are aromatic.

19. Draw chair or boat conformations to represent the highest and lowest energy conformations of trans-1-tertbuty-3-methylcyclohexane?

20. Give the most likely product that would form the following reaction sequence.

21. What will be the most likely product in the following reaction?.

22. Rank the following in order of increasing reactivity in the presence of methoxide.
A B C

23. Draw Newman projections to represent the highest and lowest energy conformations of pentane.

24. Give the function group generally created with a primary alcohol is treated with TsCl/pyr followed by NaOEt.

25. Which have the smallest HOMO-LUMO gap
Which have the smallest HOMO-LUMO gap? Which will absorb the shortest wavelenth UV light?
Alkene, diene, conjugated diene, conjugated triene, alkane

26. Rank the following in order of increasing pKa
Acetylene, methyl amine, methanol

27. Rank the following in order of increasing basicity
Aniline, p-methoxyaniline, p-nitroaniline, m-chloroaniline

28. Draw The transition state in the first step of following reaction.

29. Label all stereogenic centers in the following molecule as either R or S.

30. Identify the key difference in the IR of aldehydes, ketones, carboxylic acids, alcohols, and amines.

31. Predict the most likely products for the following reaction.

32. Predict the most likely products for the following reaction.

33. Draw a molecule that could give the following 13C decoupled NMR data?
Peak shift (ppm)
1 20
2 27
3 30
4 –

34. Which of the following molecules should have the strongest conjugate acid.
A B C D

35. Which of the following molecules is optically active.
A B C D

36. Draw a molecule that could be synthesized starting from an ester and two moles of a grignard reagent.

37. Draw the first step in the mechanism by which an ester undergoes soponification (hydrolysis) in the presence of NaOH.

38. Devise a synthesis for the following reaction
Devise a synthesis for the following reaction. Include all necessary reagents and indicate the order which the reagents would be added.

39. Draw the first intermediate that would form in the reaction where the following ester reacts with LiAlH4.

40. What type of isomers are the following compounds?

41. What could be true about a molecule with the following formula: C10H16?
It may contain two triple bonds
It may contain no unsaturation
It may contain a ring and two double bonds
It may contain two rings and a triple bond

42. Explain why vinyl chloride will undergo free radical polymerization more readily than ethene.

43. Draw any molecule that would likely give a peak in the 1H NMR with a quartet around 4.0 ppm.

44. Draw a reasonable energy diagram (reaction coordinate diagram) for the substitution reaction between 2-methyl-2-bromopentane and NaOH.

45. Give the most likely end product from the following reaction sequence.

46. Draw an alkyl halide that could readily undergo substitution by either SN1 or SN2.

47. Which should undergo SN1 most readily?
Benzyl bromide, 4-methylbenzyl bromide, 4-nitrobenzyl bromide, 4-methoxybenzyl bromide

48. Starting from 2-cyclopentenone, what reagents would be necessary to make 2,3-dipropylcyclopentanone?

49. If ethyl acetate were treated with ethoxide followed by dilute acid/H2O, draw the product that would most likely result.

50. Give reagents necessary to make N-methyl-1-phenyl-ethanamine in one step from acetophenone.

51. Show the antiperiplanar transition state for the elimination of bromocyclohexane.

52. Give the most likely end product from the following reaction.

53. Draw 2 functional groups that can withdraw electrons through both induction and resonance.

54. What should be the major product of the following reaction?

55. Give a molecule that could produce the following products after undergoing ozonolysis.