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2. OC(=O)C1C(C(C1C(=O)O)C(=O)O)C(=O)O

3.O=C1C=CC(=O)C2C3OC(C=C3)C21

4. Select the compound that would undergo a Diels-Alder reaction with cyclopentadiene the fastest:

5. One of the following compounds does not undergo a Diels-Alder reaction. Which one?

6. represents one of the MOs of the pentadienyl system, i.e. the pentadienyl radical, anion, or cation. Which one? B. y₂ This orbital has 1 node. Therefore, it must be the second lowest in energy.

7. One of the following representations of an MO is incorrect. Which one?

Since there is a node at C-2, the phase of the orbitals at C-1 and C-3 can't be the same.

8.* C/C=C/CC\C=C\C or C/C=C/CC/C=C/C

9. Classify the following sigmatropic rearrangement:C. [1,5]

10. Arrange the following alkenes in order of increasing electron density in the double bond. Enter your answer as a 4-digit number with the pi system with lowest electron density first and that with the highest electron density last, e.g. 1234. 2413

11. Select the picture that represents the LUMO of the allylic anion, H₂C=CH₂-CH₂:^-.

12. C[Si](C)(C)OC1=CCC(=C(C1)c2ccccc2)c3ccccc3

13.CC1=C(C=C)C(=C(C)CC1)C=C

14.

CC=CC=CC(Cl)c1ccc(O)cc1

15. CC(=O)CCC=C

16. How many electrons are involved in the following reaction? 4

17.* Compound X undergoes the photochemically induced 2+2 cycloaddition reaction shown below. Draw the structure of X.

C/C=C/C

18. COC(=O)C1=C(CC2=CC=CC=CC12)C(=O)[O]

19.O=C1C2C=CC=CC1C3CC2C=C3

20. Classify the following cylcoaddition reaction using the x+y formalism.14+2 or 2+14

21.* The following transformation is known as an electrocylcic reaction:Draw the product of the following electrocyclic reaction: C[C@H]1C=C[C@H]1C

22. Assume that you are interested in measuring substituent effects on the acidity of a series of substituted benzoic acids. You find experimentally that 4-nitrobenzoic acid is a stronger acid than benzoic acid. You suspect that the increase in acidity is due to both the inductive effect and the resonance effect of the nitro group, but you are not sure of their relative importance. You decide to measure the inductive effect of the nitro group by recording the H-NMR spectrum of an appropriate model compound. Which of the following structures would make an appropriate model? Since inductive effects are transmitted through sigma bonds, choice D is most appropriate.

23.Oc1ccccc1CCC=O

24. Select the alkene that would react fastest when treated with aqueous sulfuric acid. Protonation of the methylene group of the double bond in this structure produces a tertiary carbocation.

25. What is the highest oxidation level that a carbon atom can have in a hydrocarbon? 0

26. The reactionwill proceed fastest when G =

A. 2-F B. 3-F C. 2-CO₂CH₃ D. 3-CO₂CH₃ Enter the letter that corresponds to the group of your choice.

27. Select the compound that would react faster with a solution of KOH dissolved in ethanol:

28. The labeled hydrogens in are enantiotopic. One is called the pro-R hydrogen, while the other is called the pro-S hydrogen. Which one is pro-R? H1

29. Consider the following information:

Based on the data provided, calculate the relative reactivity of a secondary hydrogen compared to that of a primary hydrogen. Express you answer to two significant figures. 3.2/1 The theoretical ratio of secondary to primary is 4/6 or 0.67/1. The experimental ratio is 68/32 or 2.125/1. Therefore, the experimental ratio is 2.125/0.67 = 3.2 times greater than the theoretical ratio.

30. An unknown compound contained 89.5% C and 10.5% H. The material rapidly decolorized a solution of Br₂ in CCl₄. CC1CCCC2=C1C=CC2