2.Predict and arrange the reactivity of the following compounds in ascending order when reacting with HBr.

(A)2＜3＜5＜1＜4
(B)5＜3＜2＜4＜1
(C)1＜2＜5＜3＜4
(D)4＜1＜3＜5＜2
(E)2＜5＜3＜1＜4

3. Which of the following structures, if flat, can be considered aromatic? (A) 1 only. (B) 3 and 5 only. (C) 2 and 4 only. (D) 1 and 3 only. (E) None of the above.

4. Which of the following is a correct Diels-Alder reaction product of the following reaction? (A)(B)(C)(D)(E)

5. Which of the following reaction will NOT give the product as shown? (A)(B)(C)(D)(E)

6. Consider a system in which an ester is hydrolyzed in a base catalyzed hydrolysis using potassium hydroxide as the base. After the reaction, what will happen theoretically concerning the acidity of the reaction mixture when compared to the beginning of the reaction? (A) The mixture will become more basic compared to the beginning. (B) The mixture will become more acidic compared to the beginning. (C) The acidity of the reaction mixture will not change. (D) The concept of acidity cannot be applied to organic system. (E) The exact situations depend on the actual structure of the ester.

7. Which of the following position is the most reactive towards electrophilic aromatic substitution? (A)A(B)B(C)C(D)D(E)E

8. Describe the number of signals and their splitting in the 1H NMR of the following compound: (A) 7 signals: 1 singlet, 2 doublets, 1 triplet, 3 quartet (B) 6 signals: 1 singlet, 3 doublets, 1 triplet, 1 quartet (C) 7 signals: 4 doublets, 2 triplet, 1 quartet (D) 7 signals: 1 singlet, 4 doublets, 1 triplet, 1 quartet (E) 8 signals: 2 singlet, 4 doublets, 1 triplet, 1 quartet

9.Which of the following pair of structures represent an identical compound? (A)(B)(C)(D)(E)

10. Which of the following solvent is the most soluble in water? (A) hexanoic acid (B) dichloromethane (C) dimethylformamide (D) 1-butanol (E) ethyl acetate

11. Which of the following compound is the most reactive in an SN1 reaction? (A)(B)(C)(D)(E)

12. Which of the following reaction conditions will give the desire product as shown? Reaction conditions: (1)O3 (2) (3) Excess HBr, then excess KOH (4) BuLi, then H2O (A) (1) and (2) only (B) (2) and (3) only (C) (2), (3) and (4) only (D) All of the above (E) None of the above

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