8.Which of the following compounds is chiral? 
(A)
(B)
(C)
(D)
(E)

9.As viewed from the angle indicated, draw the Newman projection of the conformer of the following compound where the two methyl groups are gauche. (A)(B)(C)(D)(E)

10.For the following reaction sequence, which molecule is expected as the major product? (A)(B)(C)(D)(E)

11.Examine the transforration shown below and then indicate which of the following statements is correct.  (A)This is a reduction reaction. (B)The product is a protected ester. (C) The product has two resonance structures. (D)The entropy of the reaction decreases. (E) The unsaturation numbers of the starting material and the product are different.

12. A professor wanted to invent a C-H oxidation reaction, in which n-pentane could be oxidized to give mono- hydroxy products without skeletal rearrangement. In theory, how many isomers could be produced in this transformation?(A)3(B)4(C)5(D)6(E)7

13. A graduate student found four reagent vials (I, II, III, IV) with unclear labels. A lab manager mentioned that one of the reagents could be chlorine-substituted alkane (R-Cl). The graduate student quickly made a judgment after collecting the mass spectra of these four samples. Based on the data, please tell us which vial contains a chloroalkane compound. (A)reagent vial I(B) reagent vial Il (C)reagent vial III (D)reagent vial IV(E)None of them is a chlorine-substituted compound.

14. One of the following chloronorbornanes undergoes E2 eiimination much faster than others. Considering the E2 mechanism and structural features of the norbornane systemns, determine which one is faster to give the corresponding alkene product. (A)(B)(C)(D)(E)The above compounds react equally fast.

15.A student reported that an acid (H+X- ) promoted a reaction of the epoxide to give a product. By analyzing the1H NMR spectrum of the product, the student saw that the most downfield peak is 3.4 ppm. Considering the reactivity of the epoxide and the spectroscopic data of the product, what is the most reasonable structure of the product?(A)(B)(C)(D)(E)

16. Based on your knowledge of current organic chemistry, which of the following reactions leads to a correct major product? Note: Only key reagents are shown, and assuming that appropriate workup procedures are applied. (A)(B)(C)(D)(E)

17. What is the major product for the following reaction? (A)(B)(C)(D)(E)

18. Which of the following reactions will NOT give a ketone as a major product? (A)(B)(C)(D)(E)

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