4. The expected major product of HCl addition to the alkene would be:
 
(A)
(B)
(C)
(D)
(E)

5.In the following substitution reaction, diastereoselectivity. After analyzing the ster compound A was converted to compound B in excellent ereochemcal relationship between A and B, it was proposed that chloride attacked a key intermediate, resulting in the forination of B. The structure of the key intermediate is most likely to be:   (A)(B)(C)(D)(E)

6.Rank the following protons (I, II, and IlI) in decreasing order (most to least) of acidity. (A)II>IlI>I(B)I>II>IlI(C) IlI>I>II (D)IlI＞II>I (E)I>IlI>II

7.The light-induced bromination of the C-H bond of alkanes with molecular bromine could be a regioselective process. The reactions involved the fomnation of radical intermediates. Identify the major product of the following reaction. (A)(B)(C)(D)(E)

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.

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